CN1842272A - 用于防治有害昆虫和蜘蛛的腙衍生物 - Google Patents
用于防治有害昆虫和蜘蛛的腙衍生物 Download PDFInfo
- Publication number
- CN1842272A CN1842272A CNA2004800146224A CN200480014622A CN1842272A CN 1842272 A CN1842272 A CN 1842272A CN A2004800146224 A CNA2004800146224 A CN A2004800146224A CN 200480014622 A CN200480014622 A CN 200480014622A CN 1842272 A CN1842272 A CN 1842272A
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- Prior art keywords
- alkyl
- group
- halogenated
- phenyl
- carbonyl
- Prior art date
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
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- 229960005137 succinic acid Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
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- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
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- 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
- A01N37/28—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 group; Thio analogues thereof
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
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-
- A—HUMAN NECESSITIES
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- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
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- 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
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-
- A—HUMAN NECESSITIES
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- 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
- A01N43/80—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 1,2
-
- A—HUMAN NECESSITIES
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- 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
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- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及一种防治昆虫或蜘蛛的方法,包括使昆虫或蜘蛛,其栖息地,繁殖地,食物源,其中昆虫或蜘蛛生长或可能生长的植物、种子、土壤、区域、材料或环境或需要防止昆虫或蜘蛛侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的通式(I)化合物或其盐接触,其中Ar为环状基团,n为0或1,X为CO或SO2且R1-R4如权利要求1所定义。
Description
本发明涉及一种防治有害昆虫和蜘蛛的方法。
尽管目前可以获得用于防治有害昆虫和蜘蛛的市售杀虫剂,但由昆虫和蜘蛛引起的对生长和收获作物的损害以及其他公害,如疾病传播仍然存在。因此,一直需要提供可用于防治有害昆虫和蜘蛛的化合物。
因此,本发明的目的是提供可以用于防治有害昆虫和蜘蛛的化合物。
R.J.Cremlyn(J.Chem Soc.C 1967,77-81)描述了某些磺胺酰肼(sulfanil hydrazide)具有杀真菌活性。
WO 87/66133描述了可以用于杀灭影响温血动物和人类的体内寄生虫如线虫、吸虫和绦虫的酰腙。
US 3066023公开了在静电复印用材料中作为光导绝缘层的组分的芳酰腙。
WO 99/01423公开了可以用作胰增血糖素拮抗剂或反激动剂的芳酰腙的制备。
EP-A 322691公开了用作制备1-酰基吡唑啉的前体的芳酰基腙。
本申请的发明人惊人地发现了式I化合物或其盐可以用于防治昆虫和蜘蛛:
其中:
Ar为选自如下的环状基团:苯基,萘基和具有1-4个相互独立地选自O、N和S的杂原子的5或6元杂环基团,其中该5或6元杂环基团可以与1或2个苯环稠合,其中该环状基团可以具有1、2、3、4或5个取代基Ra,所述取代基Ra相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基、R5R6N-CO-、苯基、苄基和苯氧基,其中苯基、苄基和苯氧基可以被1、2、3、4或5个取代基Rb取代,所述取代基Rb相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO-;
X为CO或SO2;
R1为H、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C2-C10卤代炔基或可以被1-5个相互独立地选自如下的取代基取代的苯基:卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO-;
R2和R3相互独立地为H、卤素、氰基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、羟基-C1-C10烷基、C1-C10烷氧基-C1-C10烷基、卤代-C1-C10烷氧基-C1-C10烷基、C1-C10烷氧羰基-C1-C10烷基、卤代-C1-C10烷氧羰基-C1-C10烷基或可以被1-5个相互独立地选自如下的取代基取代的苯基:卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO;
R4为选自苯基、吡啶基、嘧啶基或呋喃基、噻吩基的芳族基团,其中芳族基团可以带有1、2、3、4或5个取代基Rc,所述取代基Rc相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基、R5R6N-CO-和可以被1、2、3、4或5个取代基Rd取代的苯氧基,所述取代基Rd相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO;或
R2和R4与它们所键合的碳原子一起形成苯环或具有1或2个相互独立地选自O、N和S的杂原子的5或6元杂环,其中苯环和5或6元杂环可以与苯环稠合,其中苯环和5或6元杂环和/或它们所稠合的苯环可以带有1、2、3或4个取代基Re,所述取代基Re相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C2-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C2-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基、R5R6N-CO和可以被1、2、3、4或5个取代基Rf取代的苯氧基,所述取代基Rf相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO,其中5或6元杂环可以含有1个羰基作为环成员;
R5和R6相互独立地为H或C1-C10烷基;和
n为0或1。
本发明因此涉及一种防治有害昆虫和蜘蛛的方法,包括使昆虫或蜘蛛,其栖息地,繁殖地,食物源,其中昆虫或蜘蛛生长或可能生长的植物、种子、土壤、区域、材料或环境或需要防止昆虫或蜘蛛侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的式I的腙化合物接触。
本发明尤其涉及一种保护作物免受昆虫或蜘蛛侵袭或侵染的方法,包括使作物与杀虫有效量的上述式I化合物接触。
合适的通式I化合物包括可能存在的所有可能立体异构体(顺式/反式异构体)及其混合物。立体异构中心例如为腙基的碳原子(N=C)和带有基团R3和R4的碳原子。合适的化合物还包括可能的对映体和外消旋混合物。
根据本发明适合使用的式I化合物的盐尤其是可农用盐。它们可以常规方法形成,例如通过使该化合物与所述阴离子的酸反应。
合适的盐的实例包括化合物I与马来酸、二马来酸、富马酸、二富马酸、甲磺酸、甲磺酸和琥珀酸的加合物。此外,作为“盐”还包括可以与例如胺类、金属、碱土金属碱或季铵碱形成的那些,包括两性离子类。适合作为成盐剂的金属和碱土金属氢氧化物包括钡、铝、镍、铜、锰、钴、锌、铁、银、锂、钠、钾、镁或钙的盐。额外的成盐剂包括氯化物、硫酸盐、乙酸盐、碳酸盐、氢化物和氢氧化物。理想的盐包括化合物I与马来酸、二马来酸、富马酸、二富马酸和甲磺酸的加合物。
本文所用的术语“具有1-4个相互独立地选自O、N和S的杂原子的5或6元杂环基团”是指芳族和非芳族环如具有1-4个,优选1、2或3个杂原子作为环成员的饱和或部分不饱和基团。
杂芳族环的实例是三嗪基、吡嗪基、嘧啶基、哒嗪基、吡啶基、噻吩基、呋喃基、吡咯基、吡唑基、咪唑基、三唑基、四唑基、噻唑基、唑基、噻二唑基、二唑基、异噻唑基或异唑基。
若5或6元杂芳族环与1或2个苯环稠合,则这是指例如喹啉基、异喹啉基、吲哚基、中氮茚基、异吲哚基、吲唑基、苯并呋喃基、苯并噻吩基、苯并噻唑基、苯并唑基、苯并咪唑基、二苯并吡咯基、二苯并呋喃基或二苯并噻吩基。
非芳族环的实例是吡咯烷基、吡唑啉基、咪唑啉基、吡咯啉基、吡唑啉基、咪唑啉基、四氢呋喃基、二氢呋喃基、二氧戊环基、间二氧杂环戊烯基(dioxolenyl)、硫杂戊环基(thiolanyl)、二氢噻吩基、唑烷基、异唑烷基、唑啉基、异唑啉基、噻唑啉基、异噻唑啉基、噻唑烷基、异噻唑烷基、氧硫杂戊环基(oxathiolanyl)、哌啶基、哌嗪基、吡喃基、二氢吡喃基、四氢吡喃基、二烷基、噻喃基、二氢噻喃基、四氢噻喃基、吗啉基和噻嗪基。
若5或6元杂环非芳族基团稠合于苯基上,则这是指例如二氢吲哚基、二氢中氮茚基、二氢异吲哚基、二氢喹啉基、二氢异喹啉基、苯并吡喃基、苯并二氢吡喃基等。
本文所用的术语“具有1或2个相互独立地选自O、N和S的杂原子的5或6元杂环,其中该5或6元杂环可以与苯环稠合”例如是指吡嗪基、嘧啶基、哒嗪基、吡啶基、噻吩基、呋喃基、吡咯基、吡唑基、咪唑基、噻唑基、唑基、异噻唑基、异唑基、喹啉基、异喹啉基、吲哚基、吲唑基、苯并呋喃基、苯并噻吩基、苯并噻唑基、苯并唑基、苯并咪唑基或苯并吡喃基且还指对5或6元杂环非芳族环以及与苯基稠合的杂环非芳族环所举例的基团。
若可以与苯环稠合的具有1或2个杂原子的5或6元杂环含有羰基作为环成员,则这是指例如吡咯烷酮基、吡唑烷酮基、吡唑啉酮基、唑烷酮基、吡啶酮基、吡喃酮基、3-吲哚氧基(indoxylyl)、2-羟基吲哚基、α-苯并吡喃酮基、苯并-γ-吡喃酮基(色酮基)等。
“卤素”应指氟、氯、溴和碘。
本文所用的术语“C1-C10烷基”指具有1-10个碳原子的支化或未支化饱和烃基,例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、庚基、辛基、2-乙基己基、壬基和癸基及其异构体。C1-C4烷基例如指甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基或1,1-二甲基乙基。
本文所用的术语“C1-C10卤代烷基”指其中部分或所有氢原子可以被上述卤原子代替的具有1-10个碳原子的直链或支化烷基(如上所述),例如C1-C4卤代烷基,如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基等。
类似地,“C1-C10烷氧基”和“C1-C10烷硫基”是指分别通过在烷基中的任意键处的氧或硫键键合的具有1-10个碳原子的直链或支化烷基(如上所述)。实例包括C1-C4烷氧基如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、异丁氧基和叔丁氧基,此外还有C1-C4烷硫基如甲硫基、乙硫基、丙硫基、异丙硫基和正丁硫基。
因此,术语“C1-C10卤代烷氧基”和“C1-C10卤代烷硫基”是指其中这些基团中的部分或所有氢原子可以被上述卤原子代替,且分别通过在烷基中的任意键处的氧或硫键键合的具有1-10个碳原子的直链或支化烷基(如上所述),例如C1-C2卤代烷氧基,如氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯一氟甲氧基、一氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基和五氟乙氧基,此外还有C1-C2卤代烷硫基,如氯甲硫基、溴甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、二氯一氟甲硫基、一氯二氟甲硫基、1-氯乙硫基、1-溴乙硫基、1-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、2,2,2-三氯乙硫基和五氟乙硫基等。
本文所用的术语“C2-C10链烯基”是指具有2-10个碳原子和在任意位置的双键的支化或未支化不饱和烃基,如乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基;
本文所用的术语“C2-C10卤代链烯基”是指其中这些基团中的部分或所有氢原子可以被上述卤原子代替的具有2-10个碳原子和在任意位置的双键的支化或未支化不饱和烃基。
类似地,本文所用的术语“C2-C10链烯氧基”是指具有2-10个碳原子和在任意位置的双键的支化或未支化不饱和烃基,该链烯基分别通过在链烯基中的任意键处的氧键键合,例如乙烯氧基、丙烯氧基等。
相应地,本文所用的术语“C2-C10卤代链烯氧基”是指具有2-10个碳原子和在任意位置的双键的支化或未支化不饱和烃基,该链烯基分别通过在链烯基中的任何键处的氧键键合,其中这些基团中的部分或所有氢原子可以被上述卤原子代替。
本文所用的术语“C2-C10炔基”是指具有2-10个碳原子和至少一个叁键的支化或未支化不饱和烃基,如乙炔基、丙炔基、1-丁炔基、2-丁炔基等。
本文所用的术语“C3-C10卤代炔基”是指具有3-10个碳原子和至少一个叁键的支化或未支化不饱和烃基,其中这些基团中的部分或所有氢原子可以被上述卤原子代替,条件是卤原子不直接与叁键键合。
本文所用的术语“C2-C10炔氧基”是指具有2-10个碳原子和至少一个叁键的支化或未支化不饱和烃基,该炔基通过在炔基的任意键处的氧键键合。
类似地,本文所用的术语“C3-C10卤代炔氧基”是指具有3-10个碳原子和至少一个叁键的支化或未支化不饱和烃基,该基团通过在炔基的任意键处的氧键键合,其中这些基团中的部分或所有氢原子可以被上述卤原子代替,条件是卤原子不直接与叁键键合。
本文所用的术语“C3-C10环烷基”是指单环3-10元饱和碳原子环,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基和环癸基。
本文所用的术语“C3-C10卤代环烷基”是指其中这些基团中的部分或所有氢原子可以被上述卤原子代替的单环3-10元饱和碳原子环(如环丙基、环丁基、环戊基、环己基、环庚基、环辛基和环癸基),例如一氯环丙基、二氯环丙基、三氯环丙基、一氟环丙基、二氟环丙基、三氟环丙基、一氯环己基、二氯环己基、三氯环己基、四氯环己基、五氯环己基和六氯环己基等。
对于式I化合物的本发明用途,特别优选取代基的下列含义,在每种情况下单独或组合:
优选使用如下式I化合物,其中:
Ar为选自如下的环状基团:苯基,萘基,具有1-3个相互独立地选自O、N和S的杂原子的5或6元杂环基团,其中该5或6元杂环基团可以与1或2个苯环稠合且其中该环状基团未被取代或如上所定义被取代,即被1、2、3、4或5个上述基团Ra取代。
特别优选使用如下式I化合物,其中:
Ar为选自如下的环状基团:苯基、三嗪基、吡嗪基、嘧啶基、哒嗪基、吡啶基、噻吩基、呋喃基、吡咯基、吡唑基、咪唑基、三唑基、噻唑基、唑基、噻二唑基、二唑基、异噻唑基、异唑基、萘基、喹啉基、异喹啉基、吲哚基、吲唑基、苯并呋喃基、苯并噻吩基、苯并噻唑基、苯并唑基、苯并咪唑基、苯并吡喃基、苯并-γ-吡喃酮基、二苯并吡喃基或芴基,其中该环状基团未被取代或如上所定义被取代。
此外,特别优选使用如下式I化合物,其中:
Ar为选自如下的环状基团:噻吩基、呋喃基、吡咯基、吡唑基、咪唑基、三唑基、唑基、异唑基、二唑基、噻唑基、异噻唑基、噻二唑基、苯基、吡啶基、吡嗪基、嘧啶基、哒嗪基、萘基、二苯并吡喃基、吲哚基、苯并咪唑基、苯并呋喃基、苯并唑基、苯并噻吩基、苯并噻唑基或苯并-γ-吡喃酮基,其中该环状基团未被取代或被1、2、3,4或5个上述基团Ra取代。
再有,特别优选使用如下式I化合物,其中:
Ar为选自如下的环状基团:噻吩基、呋喃基、吡唑基、咪唑基、异唑基、噻唑基、噻二唑基、苯基、吡啶基、吡嗪基、萘基、二苯并吡喃基、吲哚基或苯并噻吩基,其中该环状基团未被取代或被1、2、3,4或5个上述基团Ra取代。
甚至更特别优选使用如下式I化合物,其中:
Ar为选自如下的环状基团:噻吩基、呋喃基、吡唑基、咪唑基、异唑基、苯基、吡啶基、吡嗪基、萘基、吲哚基或苯并噻吩基,尤其是噻吩基、呋喃基、吡唑基、咪唑基、异唑基、苯基、吡啶基、吡嗪基、萘基或吲哚基,其中该环状基团未被取代或被1、2、3,4或5个上述基团Ra取代。
特别优选使用如下式I化合物,其中:
Ar为选自如下的环状基团:噻吩基、呋喃基、吡唑基、苯基、异唑基或吡啶基,其中该环状基团未被取代或被1、2、3,4或5个上述基团Ra取代。然而,还高度优选其中Ar为任选取代的苯基的化合物。
优选对Ar所提到的环状基团未被取代或带有1、2、3或4个取代基Ra,尤其是1、2或3个,更优选1或2个取代基Ra。
优选的取代基Ra相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C1-C10烷氧基、C1-C10卤代烷氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、苯基、苯氧基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和NR5R6-CO-。
特别优选的取代基Ra相互独立地选自卤素,羟基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,未被取代或被1-3个尤其相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基和C1-C4烷氧基的取代基Rb,尤其是卤素取代的苯基,以及未被取代或被1-3个尤其相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基和C1-C4烷氧基的取代基Rb,尤其是C1-C4卤代烷基取代的苯氧基。
更优选的取代基Ra相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和C1-C4卤代烷氧基。
尤其优选的取代基Ra相互独立地选自氟、氯、溴、C1-C4烷基、C1-C4烷氧基,尤其是甲氧基,C1-C4卤代烷氧基,尤其是二氟甲氧基或三氟甲氧基和CF3。
优选使用其中R1为H、C1-C4烷基或C1-C4卤代烷基的式I化合物。
特别优选使用其中R1为H或甲基,最优选H的式I化合物。
优选使用其中R2为H、C1-C10烷基、C1-C10卤代烷基、卤素、苯基或氰基的式I化合物。
特别优选使用其中R2为H,C1-C10烷基,尤其是C1-C4烷基,卤素,苯基或氰基的式I化合物。
此外,特别优选使用其中R2为H,C1-C10烷基,尤其是C1-C4烷基或卤素,例如甲基、乙基、异丙基、氟、氯或溴的式I化合物。最优选R2为C1-C4烷基,尤其是甲基或乙基。
优选使用其中R3为H、C1-C4烷基、C1-C4卤代烷基、卤素或苯基的式I化合物。
特别优选使用其中R3为H、C1-C4烷基、卤素或苯基,尤其是H或卤素的式I化合物。
优选使用如下式I化合物,其中:
R4为选自如下的芳族基团:苯基、吡啶基、嘧啶基、呋喃基、噻吩基或苯并呋喃基,其中该芳族基团未被取代或如上所定义被取代,即被1、2、3,4或5个上述基团Rc取代。
特别优选使用其中R4为未被取代或如上所定义被取代的苯基的式I化合物。
对R4所提到的芳族基团可以未被取代或可以带有1-5个,优选1-4个,更优选1-3个,尤其是1或2个取代基Rc。
优选的取代基Rc相互独立地选自羟基、卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C1-C10烷氧基、C1-C10卤代烷氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、R5R6N-CO-和可以被C1-C4卤代烷基取代的苯氧基。
特别优选的取代基Rc相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氰基、硝基、NR5R6和可以被C1-C4卤代烷基取代的苯氧基。
更优选的取代基Rc相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基和C1-C4卤代烷硫基,例如选自氟、氯、甲基、乙基、丙基、异丙基、丁基、氟甲基、二氟甲基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基和三氟甲硫基。
尤其优选的取代基Rc相互独立地选自卤素、C1-C4烷基和C1-C4卤代烷基。
若R4为带有1、2或3个上述取代基Rc的苯基,则该取代基中的至少一个优选位于2、4和/或6位。特别优选的取代苯基的实例是在表2和3中作为基团R4提到的那些。
另外,优选使用如下式I化合物,其中:
R2和R4与它们所键合的碳原子一起形成苯环或具有1或2个相互独立地选自O、N和S的杂原子的5或6元杂环,其中该5或6元杂环可以与苯环稠合,该5或6元杂环和/或其所稠合的苯环可以带有1、2、3或4个上述取代基Re。优选取代基Re相互独立地选自卤素,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基,C1-C4卤代烷硫基,氰基,硝基,未被取代或被1、2或3个相互独立地选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和卤素的取代基Rf取代的苯基,以及未被取代或被1-3个相互独立地选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和卤素的取代基取代的苯氧基,且其中该5或6元杂环可以含有1个羰基作为环成员。
在该可选方案中,特别优选使用如下式I化合物,其中R2和R4与它们所键合的碳原子一起形成苯基、苯并呋喃基、苯并噻吩基、吲哚基、苯并吡喃基、苯并-γ-吡喃酮基、吡唑基或呋喃基结构部分,且其中所述结构部分可以带有1、2、3或4个上述取代基Re。
此外,特别优选使用如下式I化合物,其中R2和R4与它们所键合的碳原子一起形成苯基、苯并呋喃基、苯并噻吩基或苯并吡喃基结构部分,且其中所述结构部分可以被1、2或3个取代基Re取代。
甚至更优选使用其中R2和R4与它们所键合的碳原子一起形成苯并呋喃基或苯并噻吩基结构部分的式I化合物。
在该可选方案中,R3为H或者为由R2和R4与它们所连接的碳原子一起形成的结构部分的上述取代基之一。
取代基Re尤其相互独立地选自卤素,C1-C4烷基,C1-C4卤代烷基,C1-C4卤代烷氧基,C1-C4卤代烷硫基,氰基,硝基,未被取代或被1、2或3个相互独立地选自C1-C4卤代烷基和卤素的取代基取代的苯基,以及未被取代或被C1-C4卤代烷基取代的苯氧基。优选取代基Re相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、氰基和硝基。更优选取代基Re相互独立地选自C1-C4烷基、C1-C4卤代烷基和卤素。
特别优选的基团Rb、Rd和Rf选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、氰基和硝基,尤其选自卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基。
本发明非常优选的实施方案涉及使用通式Ia的吡啶基化合物:
(Ia)
其中Ra、R1和R3如本文所定义,
m为0、1、2或3,
R2a为H或C1-C4烷基,和
R4a为可以带有1、2、3或4个如本文所定义的取代基Rc的苯基。
当R2a为C1-C4烷基且额外满足下列条件i)-iv)之一时,化合物Ia是新的且因此为本发明的一部分:
i)m不为0或
ii)R4a带有至少一个不为氢的取代基Rc,或
iii)R1不为氢,或
iv)R2a不为甲基。
在式Ia中,优选其中m为0、1或2的化合物。
优选式Ia中的Ra具有表示为优选、更优选、特别优选或尤其优选的含义之一。最优选Ra为卤素,尤其是F、Cl或Br,C1-C4烷基,尤其是甲基或乙基、苯基、二氟甲基、三氟甲基或C1-C4烷氧基,尤其是甲氧基。
在式Ia化合物中,优选其中R1和R3相互独立地具有表示为优选、更优选、特别优选或尤其优选的含义之一的那些。最优选其中R1和R3为氢的化合物Ia。
优选取代基Rc(若存在的话)具有表示为优选、更优选、特别优选或尤其优选的含义之一。Rc尤其选自F、Cl、甲氧基或甲基。取代的苯基尤其选自表3或4中对R4所给含义之一,尤其选自2-氟苯基、3-氟苯基、4-氟苯基、2,4-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,6-二氟苯基、2,4,6-三氟苯基、2-氯苯基、3-氯苯基、3,5-二氯苯基、2,6-二氯苯基、4-氯苯基、2-氟-4-氯苯基、3-氟-4-三氟甲基苯基、3,4,5-三氟苯基、2-三氟甲氧基苯基、3-三氟甲氧基苯基、4-三氟甲氧基苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-二氟甲氧基苯基、3-二氟甲氧基苯基、4-二氟甲氧基苯基。然而,还高度优选其中R4a为未取代苯基的化合物Ia。
在式Ia中R2a最优选为甲基或乙基。
本发明的另一非常优选实施方案涉及使用通式Ib的异唑化合物:
其中n、X、R1、R2、R3和R4如本文所定义,和
Ar为可以带有1或2个如本文所定义的取代基Ra的异唑基。
当若Ar为取代的4-异唑基,则Ar不带有任选取代的苯基作为基团Ra时,这些化合物是新的且也为本发明的一部分。
在式Ib的化合物中,优选其中n、X、Ra、R1、R2、R3和R4相互独立地具有表示为优选、更优选、特别优选或尤其优选的含义之一的那些。变量R1、R2、R3和Ra尤其具有下列含义:
R1为H,
R2为H或C1-C4烷基,最优选甲基或乙基,
R3为H,和
R4为可以带有1、2、3或4个如本文所定义的取代基Rc的苯基。
优选取代基Rc(若存在的话)具有表示为优选、更优选、特别优选或尤其优选的含义之一。Rc尤其选自F、Cl、甲氧基或甲基。取代的苯基尤其选自表3或4中对R4所给的含义之一,尤其选自2-氟苯基、3-氟苯基、4-氟苯基、2,4-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,6-二氟苯基、2,4,6-三氟苯基、2-氯苯基、3-氯苯基、3,5-二氯苯基、2,6-二氯苯基、4-氯苯基、2-氟-4-氯苯基、3-氟-4-三氟甲基苯基、3,4,5-三氟苯基、2-三氟甲氧基苯基、3-三氟甲氧基苯基、4-三氟甲氧基苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-二氟甲氧基苯基、3-二氟甲氧基苯基、4-二氟甲氧基苯基。然而,还高度优选其中R4为未取代苯基的化合物Ia。
在式Ib中,X优选为C=O且n优选为0。
本发明另一非常优选实施方案涉及使用通式Ic的吡唑化合物:
其中n、X、R1、R2、R3和R4如权利要求1所定义,
Ar为在吡唑氮原子上带有取代基Ra2且可以额外带有1或2个如权利要求1所定义的取代基Ra的吡唑基,其中Ra2选自C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、苯基和苄基,其中苯基和苄基可以未被取代或被1、2、3、4或5个如权利要求1所定义的取代基Rb取代。
式Ic的化合物是新的且因此也为本发明的一部分。
在式Ic的化合物中,优选其中n、X、Ra、Rb、R1、R2、R3和R4相互独立地具有表示为优选、更优选、特别优选或尤其优选的含义之一的那些。
Ra2优选选自C1-C6烷基、C3-C6环烷基或苯基。在特别优选的实施方案中,Ra2为C1-C4烷基。
变量R1、R2、R3和R4尤其具有下列含义:
R1为H,
R2为H或C1-C4烷基,最优选甲基或乙基,
R3为H,和
R4为可以带有1、2、3或4个如本文所定义的取代基Rc的苯基。
优选取代基Rc(若存在的话)具有表示为优选、更优选、特别优选或尤其优选的含义之一。Rc尤其选自F、Cl、甲氧基或甲基。取代的苯基尤其选自表3或4中对R4所给的含义之一,尤其选自2-氟苯基、3-氟苯基、4-氟苯基、2,4-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,6-二氟苯基、2,4,6-三氟苯基、2-氯苯基、3-氯苯基、3,5-二氯苯基、2,6-二氯苯基、4-氯苯基、2-氟-4-氯苯基、3-氟-4-三氟甲基苯基、3,4,5-三氟苯基、2-三氟甲氧基苯基、3-三氟甲氧基苯基、4-三氟甲氧基苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-二氟甲氧基苯基、3-二氟甲氧基苯基、4-二氟甲氧基苯基。然而,还高度优选其中R4为未取代苯基的化合物Ia。
在式Ic中,X优选为C=O且n优选为0。
本发明的非常优选实施方案涉及使用通式Id的苯基化合物:
(Id)
其中Ra、R1和R3如本文所定义,
m为1、2或3,
R2d为H或C1-C4烷基,和
R4d为可以带有1、2、3或4个如本文所定义的取代基Rc的苯基。
在式Id中,优选其中m为1或2的化合物。
优选式Id中的Ra具有表示为优选、更优选、特别优选或尤其优选的含义之一。最优选Ra为卤素,尤其是F、Cl或Br,C1-C4烷基,尤其是甲基或乙基、苯基、二氟甲基、三氟甲基或C1-C4烷氧基,尤其是甲氧基。最优选至少一个基团Ra为卤素,尤其是氟。
在式Id的化合物中,优选其中R1和R3相互独立地具有表示为优选、更优选、特别优选或尤其优选的含义之一的那些。最优选其中R1和R3为氢的化合物Ia。
优选取代基Rc(若存在的话)具有表示为优选、更优选、特别优选或尤其优选的含义之一。Rc尤其选自F、Cl、甲氧基或甲基。取代的苯基尤其选自表3或4中对R4所给的含义之一,尤其选自2-氟苯基、3-氟苯基、4-氟苯基、2,4-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,6-二氟苯基、2,4,6-三氟苯基、2-氯苯基、3-氯苯基、3,5-二氯苯基、2,6-二氯苯基、4-氯苯基、2-氟-4-氯苯基、3-氟-4-三氟甲基苯基、3,4,5-三氟苯基、2-三氟甲氧基苯基、3-三氟甲氧基苯基、4-三氟甲氧基苯基、2-三氟甲基苯基、3-三氟甲基苯基、4-三氟甲基苯基、2-氟甲氧基苯基、3-二氟甲氧基苯基、4-二氟甲氧基苯基。
在式Id中,R2d最优选为甲基或乙基。
就特殊立体异构体而言,优选使用其中C/N双键处的构型为E的式I化合物。还优选使用对C/N双键而言呈E/Z异构体的混合物,其中E异构体占主导。
此外还优选使用其中R2和R4相互呈顺式连接的式I化合物。还优选就R2和R4的相互位置而言呈顺式/反式异构体的混合物,其中顺式异构体占主导。
式I化合物可以使用通常被合成有机化学家已知的技术容易地合成。示例性合成方法例如描述于WO 87/06133中。
例如,可以使合适的酰肼与醛类或酮类反应而形成酰腙:
肉桂醛和类似的酮类可以根据文献程序由苯甲醛和脂族酮类或醛类得到(Organikum,Johann Ambrosius Barth Verlag,Heidelberg,1996,第493-495页)。
磺酰腙(X=SO2)可以类似方式由对应的磺酰肼开始而得到(例如Munshi,Shah,Trivedi,Indian J.Chem.1963,1,318-320):
若不可市购,则原料(酰肼)可以根据文献程序例如由羧酸酯(Ar-(CH2)n-COORa)或其他酸衍生物如Ar-(CH2)n-COY(Y=卤素)制备(例如Khan,Siddiqui,Bhatt,Oriental Journal of Chemistry 2002,18,163-164),其中使后二者与肼反应而形成对应的酰肼。另外,可以使羧酸(Ar-(CH2)n-COOH)与被保护的肼在偶联试剂如DCC或DIC存在下反应(根据Guan,Green,Bergstrom,J.Comb.Chem.2000,2,297-300)并随后除去保护基团(Messina,Botta,Corelli,Paladino,Tetrahedron Asymm.2000,11,4895-4901;Greene,Wuts,Protective Groups in OrganicSynthesis(有机合成中的保护基团),第2版,1991,第309页):
*P=保护基团;Ra=C1-C10烷基
磺酰肼(X=SO2)可以类似方式由对应的磺酸衍生物开始,例如由对应的磺酸(Ar-(CH2)n-SO2OH)或其他衍生物如磺酰卤(Ar-(CH2)n-SO2Y;Y=卤素)开始而得到(例如El-Maghrabi,Mohamed,J.Chem.Tech.Biotechnol.1983,33A,25-32):
*P=保护基团;Ra=C1-C10烷基
若单个化合物I不能通过上述途径得到,则可以通过衍生其他化合物I或通过所述合成途径的常规改进而制备它们。
式I化合物的制备可能导致它们以异构体混合物(立体异构体、对映体)得到。需要的话,可以通过常用于该目的的方法如也在旋光吸附物上的结晶或层析而拆分它们,从而得到纯异构体。
根据本发明,通式I的化合物用于防治有害昆虫和蜘蛛。具体而言,它们用于防治下列动物害虫:
鳞翅目昆虫(鳞翅目),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、Alabama argillacea、黎豆夜蛾(Anticarsia gemmatalis)、Argyresthia conjugella、Autographa gamma、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、Cirphisunipuncta、苹果小卷蛾(Cydia pomonella)、Dendrolimus pini、Diaphanianitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Eariasinsulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetria bouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothisvirescens)、玉米穗虫(Heliothis zea)、菜螟(Hellula undalis)、Hiberniadefoliaria、美国白蛾(Hyphantria cunea)、Hyponomeuta malinellus、番茄虫蛾(Keifria lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygmaexigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletis blancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostege sticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantriamonacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosomaneustria)、甘蓝夜蛾(Mamestra brassicae)、Orgyia pseudotsugata、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophoragossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutellaxylostella)、大豆夜蛾(Pseudoplusia includens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotroga cerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、Spodoptera eridania、草地夜蛾(Spodopterafrugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodopteralitura)、Thaumatopoea pityocampa、Tortrix viridana、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis,
甲虫(鞘翅目),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agrioteslineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallus solstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、甜菜隐食甲(Atomaria linearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotomatrifurcata、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderusvespertinus、石刁柏负泥虫(Crioceris asparagi)、Diabrotica longicornis、Diabrotica 12-punctata、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ipstypographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lemamelanopus)、马铃薯叶甲(Leptinotarsa decemlineata)、Limoniuscalifornicus、稻水象甲(Lissorhoptrus oryzophilus)、Melanotus communis、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、辣根猿叶甲(Phaedon cochleariae)、Phyllotreta chrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popillia japonica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilusgranaria),
双翅目昆虫(双翅目),例如埃及伊蚊(Aedes aegypti)、剌扰伊蚊(Aedesvexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anophelesmaculipennis)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、高粱瘿蚊(Contarinia sorghicola)、Cordylobia anthropophaga、尖音库蚊(Culexpipiens)、瓜实蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossina morsitans)、Haematobiairritans、Haplodiplosis equestris、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、麦瘿蚊(Mayetiola destructor)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、瑞典麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、葱蝇(Phorbiaantiqua)、萝卜蝇(Phorbia brassicae)、麦地种蝇(Phorbia coarctata)、樱桃实蝇(Rhagoletis cerasl)、苹果实蝇(Rhagoletis pomonella)、Tabanusbovinus、Tipula oleracea和欧洲大蚊(Tipula paludosa),
蓟马(缨翅目),例如兰蓟马(Dichromothrips corbetti)、烟褐蓟马(Frankliniella fusea)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothrips citri)、稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci),
膜翅目昆虫(膜翅目),例如新疆菜叶蜂(Athalia rosae)、Atta cephalotes、Atta sexdens、Atta texana、Hoplocampa minuta、Hoplocampa testudinea、小黄家蚁(Monomorium pharaonis)、Solenopsis geminata和红火蚁(Solenopsis invicta),
异翅目昆虫(异翅目),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercuscingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygaster integriceps)、烟草蝽(Euschistus impictiventris)、棉铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubea insularis和Thyanta perditor,
同翅目昆虫(同翅目),例如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、Aphis forbesi、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶镳子蚜(Aphisgrossulariae)、希奈德蚜(Aphis schneideri)、Aphis spiraecola、接骨木蚜(Aphis sambuci)、豌豆蚜(Acyrthosiphon pisum)、茄无网蚜(Aulacorthumsolani)、银叶粉虱(Bemisia argentifolii)、飞廉短尾蚜(Brachycauduscardui)、李短尾蚜(Brachycaudus helichrysi)、桃短尾蚜(Brachycauduspersicae)、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosipha gossypii、草莓中瘤钉毛蚜(Chaetosiphonfragaefolii)、茶镳隐瘤蚜(Cryptomyzus ribis)、高加索冷杉椎球蚜(Dreyfusianordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphisradicola)、Dysaulacorthum pseudosolani、车前圆尾蚜(Dysaphisplantaginea)、梨西圆尾蚜(Dysaphis pyri)、蚕豆微叶蝉(Empoasca fabae)、李大尾蚜(Hyalopterus pruni)、茶镳苦菜超瘤蚜(Hyperomyzus lactucae)、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇长管蚜(Macrosiphon rosae)、巢莱修尾蚜(Megoura viciae)、Melanaphispyrarius、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱蚜(Myzus ascalonicus)、李瘤蚜(Myzus cerasi)、桃蚜(Myzus persicae)、黄药子瘤蚜(Myzus varians)、黑茶镳子衲长管蚜(Nasonovia ribis-nigri)、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodon humuli)、苹木虱(Psyllamali)、梨木虱(Psylla piri)、Rhopalomyzus ascalonicus、玉米蚜(Rhopalosiphum maidis)、禾谷缢管蚜(Rhopalosiphum padi)、苹草缢管蚜(Rhopalosiphum insertum)、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneura lanuginosa、禾谷网蚜(Sitobionavenae)、温室粉虱(Trialeurodes vaporariorum)、桔二叉蚜(Toxopteraaurantiiand)和葡萄根瘤蚜(Viteus vitifolii)。
白蚁(等翅目),例如Calotermes flavicollis、Leucotermes flavipes、欧洲散白蚁(Reticulitermes lucifugus)和Termes natalensis,
直翅目昆虫(直翅目),例如居屋艾蟋(Acheta domestica)、东方蜚蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、欧洲球螋(Forficulaauricularia)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplus femur-rubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲蟑螂(Periplaneta americana)、美洲沙漠蝗(Schistocerca americana)、Schistocerca peregrina、Stauronotus maroccanus和庭疾灶螽(Tachycinesasynamorus),
蛛形纲(Arachnoidea),如蜘蛛(蜱螨目),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyommaamericanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argaspersicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssus gallinae)、绵羊疥病(Psoroptesovis)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),以及瘿螨科(Eriophyidae),如斯氏刺瘿螨(Aculusschlechtendali)、桔皱叶刺瘿螨(Phyllocoptrata oleivora)和桔芽瘿螨(Eriophyes sheldoni);跗绒螨科(Tarsonemidae),如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨科(Tenuipalpidae),如紫红短须螨(Brevipalpus phoenicis);叶螨科(Tetranychidae),如朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果全爪螨(Panonychus ulmi)、柑桔全爪螨(Panonychus citri)和草地小爪螨(oligonychus pratensis)。
式I化合物优选用于防治鳞翅目、缨翅目、同翅目和蜱螨目害虫,更优选用于防治鳞翅目和同翅目昆虫。
式(I)化合物可以通过使植物/作物与杀虫有效量的式(I)化合物接触而用于保护生长植物和作物以防被昆虫或蜘蛛侵袭或侵染。术语“作物”是指生长的作物和收获的作物二者。
可以通过本领域已知的任何施用方法使昆虫、蜘蛛、植物和/或其中植物生长的土壤或水与本发明化合物I或包含它们的组合物接触。这里的“接触”包括直接接触(将化合物/组合物直接施用于昆虫、蜘蛛和/或植物上,通常直接施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于昆虫、蜘蛛的生长场所和/或植物上)二者。
此外,昆虫或蜘蛛可以通过使目标害虫、其食物供应源或其生长场所与杀虫有效量的式(I)化合物接触而防治。这里的施用可以在生长场所、生长的作物或收获的作物被害虫侵染之前或之后进行。
“生长场所”是指栖息地,繁殖地,其中害虫或寄生虫生长或可能生长的植物、种子、土壤、区域、材料或环境。
通常而言,为了用于处理作物植株,本发明化合物和/或组合物的施用率可以为约0.1至约4000g/公顷,理想的是约25至约600g/公顷,更理想的是约50至约500g/公顷。为了用于处理种子,典型施用率为约1至约500g/kg种子,理想的是约2至约300g/kg种子,更理想的是约10至约200g/kg种子。在材料保护中的常规施用率例如为约0.001至约2000g,理想的是约0.005至约1000g活性化合物/立方米被保护材料。
可以将化合物I转化成常规配制剂,例如溶液、乳液、微乳液、悬浮液、可流动浓缩物、粉剂、粉末、糊和颗粒。使用形式取决于特定的目的;在任何情况下都应确保本发明化合物精细和均匀地分布。
配制剂以已知方式制备,例如通过将活性成分与溶剂和/或载体混合来制备,需要的话使用乳化剂和分散剂,若将水用作稀释剂,则还可以将其他有机溶剂用作辅助溶剂。合适的助剂主要是:溶剂如芳族化合物(例如二甲苯),氯代芳族化合物(例如氯苯),链烷烃类(例如矿物油馏分),醇类(例如甲醇、丁醇),酮类(例如环己酮),胺类(例如乙醇胺、二甲基甲酰胺)和水;载体如磨碎的天然矿物(例如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(例如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸、烷基硫酸、烷基磺酸、脂肪醇硫酸和脂肪酸及其碱金属和碱土金属盐,硫酸化脂肪醇乙二醇醚的盐,磺化萘和萘衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚或甲醛的缩合产物,聚氧乙烯辛基苯基醚,乙氧基化异辛基酚、辛基酚和壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备直接可喷雾溶液、乳液、糊或油分散体的物质是中沸点到高沸点的矿物油馏分如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如苯、甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、氯仿、四氯化碳、环己醇、环己酮、氯苯、异佛尔酮,强极性溶剂如二甲基甲酰胺、二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和粉剂可以通过将活性物质和固体载体混合或一起研磨来制备。
颗粒(如涂敷颗粒、压实颗粒、浸渍颗粒和均质颗粒)可以通过使活性成分与固体载体粘附而制备。固体载体实例为矿土如硅石、硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素,植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
本发明的该类配制剂或组合物包括本发明的式I化合物(或其组合)以及与其相混合的一种或多种可农用惰性、固体或液体载体。这些组合物含有杀虫有效量的所述化合物,其量可以随具体化合物、目标害虫和使用方法而变化。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性成分。该活性成分以90%-100%,优选95%-100%的纯度(根据NMR光谱)使用。
下列为配制剂实例:
I.将5重量份本发明化合物与95重量份细碎高岭土均匀混合。这得到包含5重量%活性成分的粉剂。
II.将30重量份式I化合物与92重量份粉状硅胶和8重量份喷雾于该硅胶表面上的石蜡油的混合物均匀混合。这得到具有良好粘附性能的活性成分配制剂(包含23重量%活性成分)。
III.将10重量份式I化合物溶于由90重量份二甲苯、6重量份的8-10mol氧化乙烯与1mol油酸N-单乙醇酰胺的加合物、2重量份十二烷基苯磺酸钙和2重量份的40mol氧化乙烯与1mol蓖麻油的加合物组成的混合物中(包含9重量%活性成分)。
IV.将20重量份式I化合物溶于由60重量份环己酮、30重量份异丁醇、5重量份的7mol氧化乙烯与1mol异辛基酚的加合物和5重量份的40mol氧化乙烯与1mol蓖麻油的加合物组成的混合物中(包含16重量%活性成分)。
V.将80重量份式I化合物与3重量份二异丁基萘-α-磺酸的钠盐、10重量份来自亚硫酸盐废液的木素磺酸的钠盐和7重量份粉状硅胶均匀混合,并在锤磨机中研磨该混合物(包含80重量%活性成分)。
VI.将90重量份式I化合物与10重量份N-甲基-α-吡咯烷酮混合,得到适于以微滴形式使用的溶液(包含90重量%活性成分)。
VII.将20重量份式I化合物溶于由40重量份环己酮、30重量份异丁醇、20重量份的7mol氧化乙烯与1mol异辛基酚的加合物以及10重量份的40mol氧化乙烯与1mol蓖麻油的加合物组成的混合物中。将该溶液倾入100,000重量份水中并使其在其中精细分布,得到包含0.02重量%活性成分的水分散体。
VIII.将20重量份式I化合物与3重量份二异丁基萘-α-磺酸的钠盐、17重量份来自亚硫酸盐废液的木素磺酸的钠盐和60重量份粉状硅胶均匀混合,并在锤磨机中研磨该混合物。将该混合物精细地分散在20,000重量份水中,得到包含0.1重量%活性成分的喷雾混合物。
活性成分可以通过喷雾、雾化、撒粉、撒播或浇灌直接使用,以其配制剂形式或由其制备的使用形式使用,例如以直接可喷溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、粉剂、撒播用材料或颗粒形式使用。使用形式完全取决于意欲的目的;在任何情况下应确保本发明的活性成分尽可能最精细地分布。
含水使用形式可以通过添加水由乳油、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为了制备乳液、糊或油分散体,可以借助湿润剂、增粘剂、分散剂或乳化剂将物质直接或溶于油或溶剂之后在水中均化。或者,可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话,溶剂或油组成的浓缩物且该类浓缩物适于用水稀释。
活性成分在即用产品中的浓度可以在宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性成分还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性成分的配制剂或甚至可以在没有添加剂的情况下施用活性成分。
根据本发明使用的组合物还可以含有其他活性成分,例如其他农药,杀虫剂,除草剂,肥料如硝酸铵、尿素、钾碱和过磷酸钙,植物毒素和植物生长调节剂、安全剂和杀线虫剂。这些额外的成分可以随后使用或与上述组合物结合使用,合适的话也仅在紧临使用之前加入(桶混合)。例如,可以在用其他活性成分处理之前或之后用本发明的组合物喷雾植物。
这些试剂可以1∶10-10∶1的重量比与本发明所用试剂混合。将化合物I或包含它们的组合物以杀虫剂的使用形式与其他杀虫剂混合通常导致更宽的杀虫作用谱。
式I化合物与与其一起使用的下列杀虫剂可用来阐述可能的组合,但并不施以任何限制:
有机磷酸酯类:高灭磷(Acephate)、谷硫磷(Azinphos-methyl)、毒死蜱(Chlorpyrifos)、毒虫畏(Chlorfenvinphos)、二嗪农(Diazinon)、敌敌畏(Dichlorvos)、百治磷(Dicrotophos)、乐果(Dimethoate)、乙拌磷(Disulfoton)、乙硫磷(Ethion)、杀螟松(Fenitrothion)、倍硫磷(Fenthion)、异唑磷(Isoxathion)、马拉硫磷(Malathion)、甲胺磷(Methamidophos)、杀扑磷(Methidathion)、甲基一六零五(Methyl-Parathion)、速灭磷(Mevinphos)、久效磷(Monocrotophos)、砜吸磷(Oxydemeton-methyl)、对氧磷(Paraoxon)、一六零五(Parathion)、稻丰散(Phenthoate)、伏杀磷(Phosalone)、亚胺硫磷(Phosmet)、磷胺(Phosphamidon)、甲拌磷(Phorate)、辛硫磷(Phoxim)、虫螨磷(Pirimiphos-methyl)、丙溴磷(Profenofos)、丙硫磷(Prothiofos)、乙丙硫磷(Sulprophos)、三唑磷(Triazophos)、敌百虫(Trichlorfon);
氨基甲酸酯类:棉铃威(Alanycarb)、丙硫克百威(Benfuracarb)、甲奈威(Carbaryl)、丁硫克百威(Carbosulfan)、双氧威(Fenoxycarb)、呋线威(Furathiocarb)、二唑虫(Indoxacarb)、灭虫威(Methiocarb)、灭多虫(Methomyl)、甲氨叉威(Oxamyl)、抗蚜威(Pirimicarb)、残杀威(Propoxur)、硫双威(Thiodicarb)、唑蚜威(Triazamate);
合成除虫菊酯类:氟氯菊酯(Bifenthrin)、氟氯氰菊酯(Cyfluthrin)、氯氰菊酯(Cypermethrin)、溴氰菊酯(Deltamethrin)、高氰戊菊酯(Esfenvalerate)、醚菊酯(Ethofenprox)、甲氰菊酯(Fenpropathrin)、杀灭菊酯(Fenvalerate)、(RS)氯氟氰菊酯(Cyhalothrin)、氯氟氰菊酯(Lambda-Cyhalothrin)、氯菊酯(Permethrin)、灭虫硅醚(Silafluofen)、氟胺氰菊酯(Tau-Fluvalinate)、七氟菊酯(Tefluthrin)、四溴菊酯(Tralomethrin)、己体氯氰菊酯(Zeta-Cypermethrin);
节肢动物生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类:定虫隆(Chlorfluazuron)、氟脲杀(Diflubenzuron)、氟螨脲(Flucycloxuron)、氟虫脲(Flufenoxuron)、氟铃脲(Hexaflumuron)、氟丙氧脲(Lufenuron)、双苯氟脲(Novaluron)、伏虫隆(Teflubenzuron)、杀虫隆(Triflumuron);噻嗪酮(Buprofezin)、茂醚(Diofenolan)、噻螨酮(Hexythiazox)、特苯唑(Etoxazole)、四螨嗪(Clofentazine);b)蜕皮激素拮抗剂:特丁苯酰肼(Halofenozide)、甲氧苯酰肼(Methoxyfenozide)、双苯酰肼(Tebufenozide);c)保幼激素类似物:蚊蝇醚(Pyriproxyfen)、蒙五一五(Methoprene)、双氧威(Fenoxycarb);d)类脂生物合成抑制剂:螺螨酯(Spirodiclofen);
各种杀虫剂:齐墩螨素(Abamectin)、灭螨醌(Acequinocyl)、虫螨脒(Amitraz)、艾扎丁(Azadirachtin)、联苯肼酯(Bifenazate)、杀螟丹(Cartap)、氟唑虫清(Chlorfenapyr)、杀虫脒(Chlordimeform)、灭蝇胺(Cyromazine)、杀螨硫隆(Diafenthiuron)、Dinetofuran、茂醚(Diofenolan)、Emamectin、硫丹(Endosulfan)、Ethiprole、喹螨醚(Fenazaquin)、锐劲特(Fipronil)、伐虫脒(Formetanate)、伐虫脒盐酸盐(Formetanate hydrochloride)、灭蚁腙(Hydramethylnon)、吡虫啉(Imidacloprid)、二唑虫(Indoxacarb)、哒螨酮(Pyridaben)、拒嗪酮(Pymetrozine)、艾克敌105(Spinosad)、硫(Sulfur)、吡螨胺(Tebufenpyrad)、噻虫嗪(Thiamethoxam)和硫环杀(Thiocyclam)。
现在通过下列实施例更详细说明本发明。
1.合成实施例
1.1制备原料
产物通过联用的高效液相色谱法/质谱法(HPLC/MS)、NMR或其熔点表征。
HPLC柱:RP-18柱(Chromolith Speed ROD,购自德国Merck KgaA)。
洗脱:乙腈+0.1%三氟乙酸(TFA)/水+0.1%TFA,比例为5∶95-95∶5,在40℃下进行5分钟。
MS:Quadrupol电喷雾离子化,80V(正方法)
1.1.1制备4-甲基噻吩甲酰肼
将142.2mg(1mmol)4-甲基噻吩甲酸、158.6mg(1.2mmol)Boc保护的肼和518mg(1mmol)N-环己基-N’-甲基聚苯乙烯碳二亚胺在8ml二氯甲烷中的混合物在室温下搅拌一夜。过滤之后加入400mg 4-苄氧基苯甲醛聚苯乙烯并搅拌一夜。在过滤并蒸发溶剂之后,得到130mg(0.51mmol,51%)Boc保护的酰肼(保留时间(RT)=2.339分钟,m/z=279[M+Na]+)。然后加入3ml1∶1的三氟乙酸/二氯甲烷。在2小时后真空除去溶剂并加入水。通过用二氯甲烷萃取(3次)并除去溶剂而分离出产物。纯度足以用于进一步的反应(RT=1.132min,m/z=157[M+H]+)。
1.2制备最终的式I的腙
1.2.1制备呋喃-2-甲酸[(苯并呋喃-2-基)亚甲基]酰肼
将219.2mg(1.5mmol)苯并[b]呋喃-2-甲醛和283.7mg(2.25mmol)呋喃-2-甲酰肼在4ml甲醇中的混合物回流3小时。冷却到室温之后,沉淀出白色固体,将其真空干燥。收率:398mg,根据1H NMR的纯度为95%。
1H NMR(d6-DMSO;400MHz):6.8(s,1H),7.3(m,1H),7.4(m,1H),7.45(m,1H),7.6(d,1H),7.7(d,1H),8.0(s,1H),8.5(s,1H),12.1(s,1H)。
以类似方式制备下表1-4所列化合物。表4中所列各化合物显示以低施用率,例如以500ppm或更低的施用率施用时对至少一种所提到的昆虫或对蚜虫的杀虫活性。
表1
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT*(HPLC/MS)) |
1 | 噻吩-2-基 | H | CH3 | H | 苯基 | |
2 | 5-氯噻吩-2-基 | H | Cl | H | 苯基 | 178-180℃ |
3 | 5-氯噻吩-2-基 | H | CH3 | H | 4-氟苯基 | 114-116℃ |
4 | 5-氯噻吩-2-基 | H | CH3 | H | 3-三氟甲基苯基 | 117-119℃ |
5 | 5-氯噻吩-2-基 | H | H | H | 4-甲氧基苯基 | |
6 | 5-氯噻吩-2-基 | H | H | H | 苯基 | 145-147℃ |
7 | 5-氯噻吩-2-基 | H | CH3 | H | 苯基 | 143-145℃ |
8 | 4,5-二氯噻吩-2-基 | H | CH3 | H | 苯基 | |
9 | 2,5-二氯噻吩-3-基 | H | H | H | 苯基 | 142-144℃ |
10 | 2,5-二氯噻吩-3-基 | H | CH3 | H | 苯基 | 129-131℃ |
11 | 4-溴-2,5-二氯噻吩-3-基 | H | H | H | 苯基 | 167-169℃ |
表2
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT*(HPLC/MS)) |
12 | 噻吩-2-基 | H | CH3 | H | 苯基 | |
13 | 噻吩-3-基 | H | H | CH3 | 苯基 | 184℃ |
14 | 噻吩-3-基 | H | H | Cl | 苯基 | 152-153℃ |
15 | 噻吩-3-基 | H | Cl | H | 苯基 | 205-212℃ |
16 | 噻吩-3-基 | H | H | H | 2-甲氧基苯基 | 164-165℃ |
17 | 苯基 | H | Cl | H | 苯基 | 3.255分钟;m/z=299[M+H]+ |
18 | 苯基 | H | CH3 | H | 苯基 | 3.239分钟;m/z=279[M+H]+ |
19 | 苯基 | H | CH3 | H | 3-氟苯基 | 3.620分钟;m/z=297[M+H]+ |
20 | 3,4-二甲氧基苯基 | H | CH3 | H | 4-氟苯基 | 3.359分钟;m/z=357[M+H]+ |
21 | 1-萘基 | H | CH3 | H | 3-氟苯基 | 4.001分钟;m/z=347[M+H]+ |
22 | 吲哚-3-基 | H | CH3 | H | 4-氟苯基 | 3.454分钟;m/z=336[M+H]+ |
23 | 吲哚-3-基 | H | CH3 | H | 3-氟苯基 | 3.464分钟;m/z=336[M+H]+ |
24 | 4-氟苯基 | H | CH3 | H | 苯基 | 3.521分钟;m/z=297[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT*(HPLC/MS)) |
25 | 4-氟苯基 | H | CH3 | H | 3-氟苯基 | 3.569分钟;m/z=315[M+H]+ |
26 | 3-甲氧基苯基 | H | CH3 | H | 苯基 | 3.450分钟;m/z=309[M+H]+ |
27 | 2-氟苯基 | H | CH3 | H | 苯基 | 3.535分钟;m/z=297[M+H]+ |
28 | 2-氟苯基 | H | CH3 | H | 4-氟苯基 | 3.571分钟;m/z=315[M+H]+ |
29 | 2-氟苯基 | H | CH3 | H | 3-氟苯基 | 3.586分钟;m/z=315[M+H]+ |
30 | 3-三氟甲基苯基 | H | CH3 | H | 苯基 | 3.855分钟;m/z=347[M+H]+ |
31 | 3-三氟甲基苯基 | H | CH3 | H | 2-氟苯基 | 3.868分钟;m/z=365[M+H]+ |
32 | 4-氯苯基 | H | CH3 | H | 4-氟苯基 | 3.760分钟;m/z=331[M+H]+ |
33 | 3-氯苯基 | H | CH3 | H | 4-氟苯基 | 3.771分钟;m/z=331[M+H]+ |
34 | 3-氯苯基 | H | CH3 | H | 3-氟苯基 | 3.785分钟;m/z=331[M+H]+ |
35 | 3-氯苯基 | H | CH3 | H | 2-氟苯基 | 3.765分钟;m/z=331[M+H]+ |
36 | 2-氯-4-氟苯基 | H | CH3 | H | 3-氟苯基 | 3.823分钟;m/z=349[M+H]+ |
表3
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
37 | 噻吩-2-基 | H | (CH2)5CH3 | H | 苯基 | 126-128℃ |
38 | 噻吩-2-基 | H | CH3 | H | 4-氟苯基 | 161-163℃ |
39 | 噻吩-2-基 | H | CH3 | H | 4-氯苯基 | 138-140℃ |
40 | 噻吩-2-基 | H | CH3 | H | 2-氯苯基 | 170-172℃ |
41 | 噻吩-2-基 | H | CH3 | H | 3-氯-4-氟苯基 | 173-175℃ |
42 | 噻吩-2-基 | H | CH3 | H | 3,4-二氟苯基 | 164-166℃ |
43 | 噻吩-2-基 | H | 苯基 | H | 4-氟苯基 | 144-146℃ |
44 | 噻吩-2-基 | H | CH(CH3)2 | H | 4-氟苯基 | 175-177℃ |
45 | 噻吩-2-基 | H | Cl | H | 4-氟苯基 | 164-166℃ |
46 | 噻吩-2-基 | H | H | H | 4-氟苯基 | 146-148℃ |
47 | 噻吩-2-基 | H | CH3 | H | 3,4,5-三氟苯基 | 202-204℃ |
48 | 噻吩-2-基 | H | Cl | H | 3-氟-4-三氟甲基苯基 | 178-180℃ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
49 | 噻吩-2-基 | H | Br | H | 苯基 | |
50 | 噻吩-2-基 | H | CH3 | H | 苯基 | |
51 | 噻吩-2-基 | H | Cl | H | 苯基 | |
52 | 噻吩-2-基 | H | H | H | 2-硝基苯基 | |
53 | 噻吩-2-基 | H | H | H | 苯基 | |
54 | 噻吩-2-基 | CH3 | H | H | 苯基 | |
55 | 噻吩-2-基 | H | CH3 | H | 2-三氟甲氧基苯基 | 163-164℃ |
56 | 噻吩-2-基 | H | CH3 | H | 3-三氟甲氧基苯基 | 148-150℃ |
57 | 噻吩-2-基 | H | H | H | 4-甲氧基苯基 | 173-174℃ |
58 | 噻吩-2-基 | H | CH3 | H | 2,4-二氟苯基 | 185-187℃ |
59 | 噻吩-2-基 | H | CH3 | H | 3-(3-三氟甲基-苯氧基)苯基 | 116-118℃ |
60 | 噻吩-2-基 | H | CH3 | H | 4-三氟甲基苯基 | 155-157℃ |
61 | 噻吩-2-基 | H | CH3 | H | 2-氟-4-三氟甲基苯基 | 188-190℃ |
62 | 噻吩-2-基 | H | CH3 | H | 3-二氟甲氧基苯基 | 118-120℃ |
63 | 噻吩-2-基 | H | CH3 | H | 4-三氟甲氧基苯基 | 150-152℃ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
64 | 噻吩-2-基 | H | CH3 | H | 2-二氟甲氧基苯基 | |
65 | 噻吩-2-基 | H | CH3 | H | 3-三氟甲基苯基 | 175-177℃ |
66 | 噻吩-2-基 | H | F | H | 苯基 | 218-222℃ |
67 | 噻吩-2-基 | H | CH3 | H | 3-氟苯基 | 153-154℃ |
68 | 噻吩-2-基 | H | H | Cl | 苯基 | 100-102℃ |
69 | 噻吩-2-基 | H | Cl | H | 苯基 | 3.465分钟;m/z=291[M+H]+ |
70 | 噻吩-2-基 | H | CH3 | H | 3-氟苯基 | 3.565分钟;m/z=289[M+H]+ |
71 | 噻吩-2-基 | H | CH3 | H | 4-氟苯基 | 3.588分钟;m/z=289[M+H]+ |
72 | 3-甲基噻吩-2-基 | H | H | H | 4-氟苯基 | 182-184℃ |
73 | 3-甲基噻吩-2-基 | H | CH3 | H | 苯基 | 175-177℃ |
74 | 3-甲基噻吩-2-基 | H | H | H | 苯基 | 178-180℃ |
75 | 3-甲基噻吩-2-基 | H | CH3 | H | 4-二氟甲氧基苯基 | 160-162℃ |
76 | 3-甲基噻吩-2-基 | H | CH3 | H | 苯基 | 3.589分钟;m/z=285[M+H]+ |
77 | 5-甲基噻吩-2-基 | H | CH3 | H | 4-氟苯基 | 156-158℃ |
78 | 5-甲基噻吩-2-基 | H | CH3 | H | 4-氯苯基 | 191-193℃ |
79 | 5-甲基噻吩-2-基 | H | CH3 | H | 4-氯-3-氟苯基 | 173-175℃ |
80 | 5-甲基噻吩-2-基 | H | CH3 | H | 3-氯-4-氟苯基 | 107-109℃ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
81 | 5-甲基噻吩-2-基 | H | CH(CH3)2 | H | 4-氟苯基 | 172-174℃ |
82 | 5-甲基噻吩-2-基 | H | Cl | H | 4-氟苯基 | 170-172℃ |
83 | 5-甲基噻吩-2-基 | H | H | H | 4-氟苯基 | 174-176℃ |
84 | 5-甲基噻吩-2-基 | H | CH3 | H | 3-三氟甲基苯基 | 173-175℃ |
85 | 5-甲基噻吩-2-基 | H | CH3 | H | 2,4-二氟苯基 | 110-112℃ |
86 | 5-甲基噻吩-2-基 | H | CH3 | H | 4-氯-2-氟苯基 | 154-156℃ |
87 | 5-甲基噻吩-2-基 | H | CH3 | H | 3-(3-三氟甲基苯氧基)苯基 | 172-180℃ |
88 | 5-甲基噻吩-2-基 | H | CH3 | H | 4-三氟甲基苯基 | 159-161℃ |
89 | 5-甲基噻吩-2-基 | H | H | H | 苯基 | 175-176℃ |
90 | 5-甲基噻吩-2-基 | H | CH3 | H | 3-二氟甲氧基苯基 | 88-90℃ |
91 | 5-甲基噻吩-2-基 | H | CH3 | H | 4-二氟甲氧基苯基 | |
92 | 5-甲基噻吩-2-基 | H | Cl | H | 苯基 | 172-176℃ |
93 | 5-甲基噻吩-2-基 | H | CH3 | H | 3-氟苯基 | 198-201℃ |
94 | 5-氯噻吩-2-基 | H | CH3 | H | 3,4-二氯苯基 | 187-189℃ |
95 | 5-氯噻吩-2-基 | H | CH3 | H | 苯基 | |
96 | 5-氯噻吩-2-基 | H | H | H | 苯基 | 3.786分钟;m/z=291[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
97 | 5-氯噻吩-2-基 | H | Cl | H | 苯基 | 4.055分钟;m/z=325[M+H]+ |
98 | 5-氯噻吩-2-基 | H | CH3 | H | 3-氟苯基 | 185-187℃ |
99 | 5-氯噻吩-2-基 | H | H | Cl | 苯基 | 191-193℃ |
100 | 3-氯-4-甲基噻吩-2-基 | H | H | H | 4-羟基-3-甲氧基苯基 | 214-216℃ |
101 | 3-氯-4-甲基噻吩-2-基 | H | H | H | 苯基 | 176-180℃ |
102 | 3-氯-4-甲基噻吩-2-基 | H | Cl | H | 苯基 | 194℃ |
103 | 3-氯-4-甲基噻吩-2-基 | H | CH3 | H | 苯基 | 161-162℃ |
104 | 3-氯-4-甲基噻吩-2-基 | H | H | Cl | 苯基 | 151-153℃ |
105 | 3-氯-4-甲基噻吩-2-基 | H | CH3 | H | 3-氟苯基 | 173-174℃ |
106 | 苯并噻吩-2-基 | H | CH3 | H | 苯基 | 194-195℃ |
107 | 苯并噻吩-2-基 | H | H | H | 苯基 | 219-220℃ |
108 | 苯并噻吩-2-基 | H | (CH2)2CH3 | H | 2,4-二氯苯基 | |
109 | 苯并噻吩-2-基 | H | CH3 | H | 3-氟苯基 | 3.964分钟;m/z=339[M+H]+ |
110 | 3-氯苯并噻吩-2-基 | H | H | H | 苯基 | 204-206℃ |
111 | 3-乙氧基噻吩-2-基 | H | CH3 | H | 苯基 | 138-140℃ |
112 | 3-乙氧基噻吩-2-基 | H | H | H | 苯基 | 99-102℃ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
113 | 噻吩-3-基 | H | CH3 | H | 3-三氟甲氧基苯基 | |
114 | 噻吩-3-基 | H | CH3 | H | 4-二氟甲氧基苯基 | 145-147℃ |
115 | 噻吩-3-基 | H | CH3 | H | 苯基 | 142-144℃ |
116 | 噻吩-3-基 | H | H | H | 苯基 | 222-225℃ |
117 | 噻吩-3-基 | H | H | H | 4-氟苯基 | 205-208℃ |
118 | 噻吩-3-基 | H | CH3 | H | 4-三氟甲氧基苯基 | |
119 | 噻吩-3-基 | H | CH3 | H | 3-三氟甲基苯基 | 168-170℃ |
120 | 呋喃-2-基 | H | Cl | H | 苯基 | 2.598分钟;m/z=275[M+H]+ |
121 | 呋喃-2-基 | H | CH3 | H | 苯基 | 2.528分钟;m/z=255[M+H]+ |
122 | 呋喃-2-基 | H | Br | H | 苯基 | 2.819分钟;m/z=319[M+H]+ |
123 | 呋喃-2-基 | H | CH3 | H | 4-甲基苯基 | 3.035分钟;m/z=269[M+H]+ |
124 | 呋喃-2-基 | H | H | H | 3,5-二氯苯基 | 3.167分钟;m/z=309[M+H]+ |
125 | 呋喃-2-基 | H | CH3 | H | 2-甲基苯基 | 2.900分钟;m/z=269[M+H]+ |
126 | 呋喃-2-基 | H | CH2CH3 | H | 苯基 | 3.042分钟;m/z=269[M+H]+ |
127 | 呋喃-2-基 | H | CH3 | H | 4-甲氧基苯基 | 2.793分钟;m/z=285[M+H]+ |
128 | 呋喃-2-基 | H | CH3 | H | 4-氯苯基 | 3.102分钟;m/z=289[M+H]+ |
129 | 呋喃-2-基 | H | H | H | 3-氟苯基 | 2.640分钟;m/z=259[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
130 | 呋喃-2-基 | H | H | H | 2-氟苯基 | 2.641分钟;m/z=259[M+H]+ |
131 | 呋喃-2-基 | H | CH3 | H | 3-氟苯基 | 3.121分钟;m/z=273[M+H]+ |
132 | 5-溴呋喃-2-基 | H | CH3 | H | 苯基 | 156-157℃ |
133 | 5-甲基异唑-3-基 | H | CH3 | H | 苯基 | 195℃ |
134 | 5-甲基异唑-3-基 | H | H | H | 苯基 | 207-208℃ |
135 | 异唑-5-基 | H | CH3 | H | 苯基 | 188-190℃ |
136 | 异唑-5-基 | H | CH3 | H | 4-氟苯基 | |
137 | 4-甲基咪唑-5-基 | H | Br | H | 苯基 | 2.197分钟;m/z=333[M+H]+ |
138 | 4-甲基咪唑-5-基 | H | CH3 | H | 2,4-二氯苯基 | 2.593分钟;m/z=337[M+H]+ |
139 | 4-甲基咪唑-5-基 | H | H | H | 3,5-二氯苯基 | 2.520分钟;m/z=323[M+H]+ |
140 | 4-甲基咪唑-5-基 | H | CH3 | H | 2-甲基苯基 | 2.310分钟;m/z=283[M+H]+ |
141 | 4-甲基咪唑-5-基 | H | H | H | 3-氟苯基 | 2.171分钟;m/z=273[M+H]+ |
142 | 4-甲基咪唑-5-基 | H | CH3 | H | 苯基 | 2.293分钟;m/z=269[M+H]+ |
143 | 4-甲基咪唑-5-基 | H | CH3 | H | 4-氟苯基 | 2.372分钟;m/z=287[M+H]+ |
144 | 4-甲基咪唑-5-基 | H | CH3 | H | 3-氟苯基 | |
145 | 1,5-二甲基吡唑-3-基 | H | H | H | 苯基 | |
146 | 1,5-二甲基吡唑-3-基 | H | CH3 | H | 苯基 | 144-146℃ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
147 | 1,5-二甲基吡唑-3-基 | H | Cl | H | 苯基 | 159-161℃ |
148 | 3-甲基吡唑-5-基 | H | CH3 | H | 苯基 | |
149 | 1-(4-氯苯基)-5-三氟甲基吡唑-4-基 | H | Cl | H | 苯基 | 104℃ |
150 | 1-(4-氯苯基)-5-三氟甲基吡唑-4-基 | H | CH3 | H | 苯基 | 165℃ |
151 | 1-(4-氯苯基)-5-三氟甲基吡唑-4-基 | H | H | H | 苯基 | 134℃ |
152 | 1,3-二甲基吡唑-5-基 | H | CH3 | H | 苯基 | |
153 | 4-氯-1,3-二甲基吡唑-5-基 | H | H | H | 苯基 | 185-187℃ |
154 | 2-甲基-4-三氟甲基噻唑-5-基 | H | CH3 | H | 苯基 | 178-179℃ |
155 | 吲哚-2-基 | H | CH3 | H | 苯基 | |
156 | 吡啶-2-基 | H | CH3 | H | 苯基 | 3.059分钟;m/z=266[M+H]+ |
157 | 吡啶-2-基 | H | Cl | H | 苯基 | 3.094分钟;m/z=286[M+H]+ |
158 | 吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.161分钟;m/z=284[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
159 | 吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.178分钟;m/z=284[M+H]+ |
160 | 吡啶-3-基 | H | CH3 | H | 苯基 | |
161 | 吡啶-3-基 | H | CH3 | H | 3-三氟甲基苯基 | |
162 | 吡啶-3-基 | H | Cl | H | 苯基 | |
163 | 吡啶-3-基 | H | CH3 | H | 4-氟苯基 | |
164 | 吡啶-3-基 | H | CH3 | H | 3-氟苯基 | 194-197℃ |
165 | 6-氯吡啶-3-基 | H | CH3 | H | 苯基 | 189-191℃ |
166 | 6-氯吡啶-3-基 | H | Cl | H | 苯基 | 205-206℃ |
167 | 6-溴吡啶-3-基 | H | H | H | 苯基 | 221-222℃ |
168 | 4-三氟甲基吡啶-3-基 | H | CH3 | H | 苯基 | |
169 | 4-三氟甲基吡啶-3-基 | H | CH3 | H | 4-氟苯基 | |
170 | 吡啶-4-基 | H | Cl | H | 苯基 | 2.319分钟;m/z=286[M+H]+ |
171 | 吡啶-4-基 | H | CH3 | H | 苯基 | 2.198分钟;m/z=266[M+H]+ |
172 | 吡啶-4-基 | H | CH3 | H | 4-氟苯基 | 2.419分钟;m/z=284[M+H]+ |
173 | 吡啶-4-基 | H | CH3 | H | 3-氟苯基 | 2.424分钟;m/z=284[M+H]+ |
174 | 2-氯吡啶-4-基 | H | CH3 | H | 苯基 | 188℃ |
175 | 2-氯吡啶-4-基 | H | H | H | 苯基 | 194-195℃ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
176 | 2-氯吡啶-4-基 | H | Cl | H | 苯基 | 200℃ |
177 | 吡嗪-2-基 | H | CH3 | H | 苯基 | |
178 | 吡嗪-2-基 | H | CH3 | H | 4-氟苯基 | |
179 | 吡嗪-2-基 | H | CH3 | H | 3-乙氧基苯基 | |
180 | 苯基 | H | CH3 | H | 苯基 | 3.122分钟;m/z=265[M+H]+ |
181 | 苯基 | H | CH3 | H | 4-氟苯基 | 3.245分钟;m/z=283[M+H]+ |
182 | 3-甲基苯基 | H | CH3 | H | 3-氟苯基 | 3.476分钟;m/z=297[M+H]+ |
183 | 4-甲基苯基 | H | CH3 | H | 苯基 | 3.080分钟;m/z=279[M+H]+ |
184 | 4-羟基苯基 | H | CH3 | H | 4-氟苯基 | 2.900分钟;m/z=299[M+H]+ |
185 | 3,4-二甲氧基苯基 | H | CH3 | H | 苯基 | 2.831分钟;m/z=325[M+H]+ |
186 | 2-甲氧基苯基 | H | CH3 | H | 4-氟苯基 | 3.410分钟;m/z=313[M+H]+ |
187 | 2-甲氧基苯基 | H | CH3 | H | 3-氟苯基 | 3.427分钟;m/z=313[M+H]+ |
188 | 4-甲氧基苯基 | H | CH3 | H | 苯基 | 2.945分钟;m/z=295[M+H]+ |
189 | 4-氟苯基 | H | CH2CH3 | H | 苯基 | 3.565分钟;m/z=297[M+H]+ |
190 | 4-氟苯基 | H | CH3 | H | 苯基 | 3.300分钟;m/z=283[M+H]+ |
191 | 4-氟苯基 | H | CH3 | H | 4-氟苯基 | 3.347分钟;m/z=301[M+H]+ |
192 | 2-氟苯基 | H | Br | H | 苯基 | 3.365分钟;m/z=348[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
193 | 2-氟苯基 | H | CH2CH3 | H | 苯基 | 3.611分钟;m/z=297[M+H]+ |
194 | 2-氟苯基 | H | CH3 | H | 苯基 | 3.345分钟;m/z=283[M+H]+ |
195 | 2-氟苯基 | H | Cl | H | 苯基 | 3.384分钟;m/z=303[M+H]+ |
196 | 2-氟苯基 | H | H | H | 苯基 | 3.046分钟;m/z=269[M+H]+ |
197 | 2-氟苯基 | H | H | H | 2-氟苯基 | 3.192分钟;m/z=287[M+H]+ |
198 | 2-氟苯基 | H | CH3 | H | 3-氟苯基 | 3.383分钟;m/z=301[M+H]+ |
199 | 2-氟苯基 | H | CH3 | H | 4-氟苯基 | 3.366分钟;m/z=301[M+H]+ |
200 | 3-氟苯基 | H | CH2CH3 | H | 苯基 | 3.620分钟;m/z=297[M+H]+ |
201 | 3-氟苯基 | H | CH3 | H | 3-氟苯基 | 3.401分钟;m/z=301[M+H]+ |
202 | 2,5-二氟苯基 | H | CH3 | H | 4-氟苯基 | 3.479分钟;m/z=319[M+H]+ |
203 | 2,5-二氟苯基 | H | CH3 | H | 3-氟苯基 | 3.494分钟;m/z=319[M+H]+ |
204 | 2,5-二氟苯基 | H | CH3 | H | 2-甲基苯基 | 3.584分钟;m/z=315[M+H]+ |
205 | 2,5-二氟苯基 | H | CH3 | H | 4-甲氧基苯基 | 3.425分钟;m/z=331[M+H]+ |
206 | 2,6-二氟苯基 | H | CH3 | H | 4-氟苯基 | 3.539分钟;m/z=319[M+H]+ |
207 | 2,6-二氟苯基 | H | CH3 | H | 3-氟苯基 | 3.485分钟;m/z=319[M+H]+ |
208 | 3,4-二氟苯基 | H | CH3 | H | 4-氟苯基 | 3.460分钟;m/z=319[M+H]+ |
209 | 3,5-二氯苯基 | H | CH3 | H | 3-氟苯基 | 3.963分钟;m/z=351[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
210 | 2-萘基 | H | CH3 | H | 3-氟苯基 | 3.699分钟;m/z=333[M+H]+ |
211 | 噻吩-2-基 | H | CH3 | H | 2-氟苯基 | 180-182℃ |
212 | 噻吩-2-基 | H | CH3 | H | 3-氯苯基 | 155-158℃ |
213 | 噻吩-2-基 | H | CH3 | H | 3-甲基苯基 | 163-165℃ |
214 | 3-甲氧基噻吩-2-基 | H | CH3 | H | 2,5-二氟苯基 | 3.310分钟;m/z=337[M+H]+ |
215 | 3-甲氧基噻吩-2-基 | H | CH3 | H | 2,3-二氟苯基 | 3.338分钟;m/z=337[M+H]+ |
216 | 3-甲氧基噻吩-2-基 | H | CH3 | H | 3,5-二氟苯基 | 3.372分钟;m/z=337[M+H]+ |
217 | 3-甲氧基噻吩-2-基 | H | CH3 | H | 3,4-二氟苯基 | 3.299分钟;m/z=337[M+H]+ |
218 | 3-甲基噻吩-2-基 | H | CH3 | H | 3,5-二氟苯基 | 3.607分钟;m/z=321[M+H]+ |
219 | 5-硝基噻吩-2-基 | H | CH3 | H | 3,5-二氟苯基 | 3.463分钟;m/z=352[M+H]+ |
220 | 2-溴-4,5-二甲基噻吩-3-基 | H | CH3 | H | 3,5-二氟苯基 | 3.847分钟;m/z=415[M+H]+ |
221 | 呋喃-2-基 | H | CH3 | H | 3,4-二氟苯基 | 3.003分钟;m/z=291[M+H]+ |
222 | 呋喃-2-基 | H | CH3 | H | 2,5-二氟苯基 | 3.002分钟;m/z=291[M+H]+ |
223 | 呋喃-2-基 | H | CH3 | H | 2,3-二氟苯基 | 3.034分钟;m/z=291[M+H]+ |
224 | 呋喃-2-基 | H | CH3 | H | 3,5-二氟苯基 | 3.085分钟;m/z=291[M+H]+ |
225 | 5-溴呋喃-2-基 | H | CH3 | H | 4-氟苯基 | 3.366分钟;m/z=353[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
226 | 5-溴呋喃-2-基 | H | CH3 | H | 3-氟苯基 | 3.371分钟;m/z=351[M+H]+ |
227 | 2-甲基呋喃-3-基 | H | CH3 | H | 3,5-二氟苯基 | 3.320分钟;m/z=305[M+H]+ |
228 | 5-甲基异唑-3-基 | H | CH3 | H | 4-氟苯基 | 3.101分钟;m/z=288[M+H]+ |
229 | 5-甲基异唑-3-基 | H | CH3 | H | 3-氟苯基 | 3.112分钟;m/z=288[M+H]+ |
230 | 5-氯甲基异唑-3-基 | H | CH3 | H | 苯基 | 3.240分钟;m/z=304[M+H]+ |
231 | 5-氯甲基异唑-3-基 | H | CH3 | H | 4-氟苯基 | 3.371分钟;m/z=322[M+H]+ |
232 | 5-氯甲基异唑-3-基 | H | CH3 | H | 3-氟苯基 | 3.297分钟;m/z=322[M+H]+ |
233 | 3-乙基异唑-5-基 | H | CH3 | H | 苯基 | 3.100分钟;m/z=284[M+H]+ |
234 | 3-乙基异唑-5-基 | H | CH3 | H | 4-氟苯基 | 3.160分钟;m/z=302[M+H]+ |
235 | 5-异丙基异唑-3-基 | H | CH3 | H | 苯基 | 3.504分钟;m/z=298[M+H]+ |
236 | 5-异丙基异唑-3-基 | H | CH3 | H | 4-氟苯基 | 3.541分钟;m/z=316[M+H]+ |
237 | 5-异丙基异唑-3- | H | CH3 | H | 3-氟苯基 | 3.553分钟;m/z=316[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
基 | ||||||
238 | 3-异丙基异唑-5-基 | H | CH3 | H | 苯基 | 3.365分钟;m/z=298[M+H]+ |
239 | 3-异丙基异唑-5-基 | H | CH3 | H | 4-氟苯基 | 3.343分钟;m/z=316[M+H]+ |
240 | 3-异丙基异唑-5-基 | H | CH3 | H | 3-氟苯基 | 3.408分钟;m/z=316[M+H]+ |
241 | 3-异丙基异唑-5-基 | H | CH3 | H | 2-氟苯基 | 3.393分钟;m/z=316[M+H]+ |
242 | 吡啶-2-基 | H | CH3 | H | 2,5-二氟苯基 | 3.161分钟;m/z=302[M+H]+ |
243 | 吡啶-2-基 | H | CH3 | H | 2,3-二氟苯基 | 3.190分钟;m/z=302[M+H]+ |
244 | 吡啶-2-基 | H | CH3 | H | 3,5-二氟苯基 | 3.229分钟;m/z=302[M+H]+ |
245 | 吡啶-2-基 | H | CH3 | H | 4-甲基苯基 | 3.224分钟;m/z=280[M+H]+ |
246 | 吡啶-2-基 | H | CH2CH3 | H | 苯基 | 3.235分钟;m/z=280[M+H]+ |
247 | 吡啶-2-基 | H | CH3 | H | 4-氯苯基 | 3.264分钟;m/z=300[M+H]+ |
248 | 吡啶-2-基 | H | H | H | 2-甲基苯基 | 2.826分钟;m/z=266[M+H]+ |
249 | 吡啶-2-基 | H | H | H | 3-氟苯基 | 2.781分钟;m/z=270[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
250 | 吡啶-2-基 | H | H | H | 2-氟苯基 | 2.744分钟;m/z=270[M+H]+ |
251 | 吡啶-2-基 | H | H | H | 2-甲氧基苯基 | 2.752分钟;m/z=282[M+H]+ |
252 | 吡啶-2-基 | H | H | H | 2-溴苯基 | 3.088分钟;m/z=330[M+H]+ |
253 | 吡啶-2-基 | H | CH3 | H | 3-甲基苯基 | 3.256分钟;m/z=280[M+H]+ |
254 | 吡啶-2-基 | H | CH3 | H | 2-甲氧基苯基 | 2.984分钟;m/z=296[M+H]+ |
255 | 吡啶-2-基 | H | H | H | 2-溴苯基 | 3.088分钟;m/z=330[M+H]+ |
256 | 吡啶-2-基 | H | CH3 | H | 3-甲基苯基 | 3.256分钟;m/z=280[M+H]+ |
257 | 吡啶-2-基 | H | CH3 | H | 2-甲氧基苯基 | 2.984分钟;m/z=296[M+H]+ |
258 | 吡啶-2-基 | H | Br | H | 苯基 | 2.998分钟;m/z=332[M+H]+ |
259 | 吡啶-2-基 | H | H | H | 2-氯苯基 | 3.027分钟;m/z=286[M+H]+ |
260 | 吡啶-2-基 | H | CH3 | H | 2-氟苯基 | 3.034分钟;m/z=284[M+H]+ |
261 | 吡啶-2-基 | H | CH3 | H | 2-氯苯基 | 3.231分钟;m/z=300[M+H]+ |
262 | 3-甲基吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.048分钟;m/z=298[M+H]+ |
263 | 3-甲基吡啶-2-基 | H | CH3 | H | 2,5-二氟苯基 | 3.105分钟;m/z=316[M+H]+ |
264 | 3-甲基吡啶-2-基 | H | CH3 | H | 2,3-二氟苯基 | 3.134分钟;m/z=316[M+H]+ |
265 | 3-甲基吡啶-2-基 | H | CH3 | H | 3,5-二氟苯基 | 3.177分钟;m/z=316[M+H]+ |
266 | 6-甲基吡啶-2-基 | H | CH3 | H | 2,5-二氟苯基 | 3.282分钟;m/z=316[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
267 | 6-甲基吡啶-2-基 | H | CH3 | H | 2,3-二氟苯基 | 3.259分钟;m/z=316[M+H]+ |
268 | 6-甲基吡啶-2-基 | H | CH3 | H | 3,5-二氟苯基 | 3.299分钟;m/z=316[M+H]+ |
269 | 6-甲基吡啶-2-基 | H | CH3 | H | 3,4-二氟苯基 | 3.260分钟;m/z=316[M+H]+ |
270 | 6-甲基吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.352分钟;m/z=298[M+H]+ |
271 | 6-溴吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.507分钟;m/z=362[M+H]+ |
272 | 6-溴吡啶-2-基 | H | CH3 | H | 2,5-二氟苯基 | 3.537分钟;m/z=382[M+H]+ |
273 | 6-溴吡啶-2-基 | H | CH3 | H | 2,3-二氟苯基 | 3.565分钟;m/z=382[M+H]+ |
274 | 6-溴吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.649分钟;m/z=362[M+H]+ |
275 | 4-氯吡啶-2-基 | H | CH3 | H | 苯基 | 3.433分钟;m/z=300[M+H]+ |
276 | 4-氯吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.470分钟;m/z=318[M+H]+ |
277 | 4-氯吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.480分钟;m/z=318[M+H]+ |
278 | 4-氯吡啶-2-基 | H | CH3 | H | 2-氟苯基 | 3.472分钟;m/z=318[M+H]+ |
279 | 6-苯基吡啶-2-基 | H | CH3 | H | 苯基 | 3.957分钟;m/z=342[M+H]+ |
280 | 6-苯基吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.978分钟;m/z=360[M+H]+ |
281 | 6-苯基吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.957分钟;m/z=360[M+H]+ |
282 | 6-苯基吡啶-2-基 | H | CH3 | H | 2-氟苯基 | 3.958分钟;m/z=360[M+H]+ |
283 | 5-三氟甲基吡啶-2-基 | H | CH3 | H | 苯基 | 3.584分钟;m/z=334[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
284 | 5-三氟甲基吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.629分钟;m/z=352[M+H]+ |
285 | 5-三氟甲基吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.578分钟;m/z=352[M+H]+ |
286 | 6-三氟甲基吡啶-2-基 | H | CH3 | H | 苯基 | 3.652分钟;m/z=334[M+H]+ |
287 | 6-三氟甲基吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.683分钟;m/z=352[M+H]+ |
288 | 6-三氟甲基吡啶-2-基 | H | CH3 | H | 2-氟苯基 | 3.678分钟;m/z=352[M+H]+ |
289 | 3,6-二氯吡啶-2-基 | H | CH3 | H | 苯基 | 3.468分钟;m/z=334[M+H]+ |
290 | 3,6-二氯吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.498分钟;m/z=352[M+H]+ |
291 | 3,6-二氯吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.513分钟;m/z=352[M+H]+ |
292 | 5-溴吡啶-3-基 | H | CH3 | H | 2,3-二氟苯基 | 3.238分钟;m/z=380[M+H]+ |
293 | 4-三氟甲基吡啶-3-基 | H | CH3 | H | 3-氟苯基 | 3.188分钟;m/z=352[M+H]+ |
294 | 4-三氟甲基吡啶-3-基 | H | CH3 | H | 3,4-二氟苯基 | 3.268分钟;m/z=370[M+H]+ |
295 | 4-三氟甲基吡啶-3-基 | H | CH3 | H | 2,5-二氟苯基 | 3.215分钟;m/z=370[M+H]+ |
296 | 4-三氟甲基吡啶-3-基 | H | CH3 | H | 2,3-二氟苯基 | 3.234分钟;m/z=370[M+H]+ |
297 | 4-三氟甲基吡啶-3-基 | H | CH3 | H | 3,5-二氟苯基 | 3.297分钟;m/z=370[M+H]+ |
298 | 吡啶-3-基 | H | CH3 | H | 2-氯苯基 | 146-148℃ |
299 | 吡啶-3-基 | H | CH3 | H | 2-氟苯基 | 137-140℃ |
300 | 吡啶-3-基 | H | CH3 | H | 3-氯苯基 | 164-166℃ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
301 | 吡啶-3-基 | H | CH3 | H | 3-甲氧基苯基 | |
302 | 吡啶-3-基 | H | CH3 | H | 3-甲基苯基 | |
303 | 吡啶-3-基 | H | CH3 | H | 4-氟苯基 | 185-188℃ |
304 | 吡啶-3-基 | H | CH3 | H | 3,5-二氟苯基 | 2.493分钟;m/z=302[M+H]+ |
305 | 吡啶-4-基 | H | 4-氟苯基 | H | 4-氯苯基 | 213-215℃ |
306 | 吡啶-4-基 | H | 苯基 | H | 2,6-二氯苯基 | 214-218℃ |
307 | 吡啶-4-基 | H | 苯基 | H | 2-氯苯基 | 201-203℃ |
308 | 吡啶-4-基 | H | CH3 | H | 3,5-二氟苯基 | 2.492分钟;m/z=302[M+H]+ |
309 | 2-氯吡啶-4-基 | H | CH3 | H | 3-氟苯基 | 3.136分钟;m/z=318[M+H]+ |
310 | 2-氯吡啶-4-基 | H | CH3 | H | 3,4-二氟苯基 | 3.211分钟;m/z=336[M+H]+ |
311 | 6-羟基-2-甲基嘧啶-4-基 | H | CH3 | H | 4-氟苯基 | 2.644分钟;m/z=315[M+H]+ |
312 | 5-溴-2-甲硫基嘧啶-4-基 | H | CH3 | H | 2-氟苯基 | 3.614分钟;m/z=411[M+H]+ |
313 | 吡嗪基 | H | CH3 | H | 3-氟苯基 | 2.783分钟;m/z=285[M+H]+ |
314 | 吡嗪基 | H | CH3 | H | 2-氟苯基 | 2.809分钟;m/z=285[M+H]+ |
315 | 苯基 | H | CH2CH3 | H | 苯基 | 3.149分钟;m/z=279[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
316 | 苯基 | H | H | H | 3-氟苯基 | 2.761分钟;m/z=269[M+H]+ |
317 | 苯基 | H | H | H | 2-氟苯基 | 2.765分钟;m/z=269[M+H]+ |
318 | 2,4-二氟苯基 | H | CH3 | H | 苯基 | 3.369分钟;m/z=301[M+H]+ |
319 | 2,4-二氟苯基 | H | CH3 | H | 4-氟苯基 | 3.411分钟;m/z=319[M+H]+ |
320 | 2,4-二氟苯基 | H | CH3 | H | 3-氟苯基 | 3.418分钟;m/z=319[M+H]+ |
321 | 2,4-二氟苯基 | H | CH3 | H | 2-氟苯基 | 3.403分钟;m/z=319[M+H]+ |
322 | 3-甲基苯基 | H | Cl | H | 苯基 | 2.850分钟;m/z=299[M+H]+ |
323 | 3-甲基苯基 | H | CH3 | H | 2-甲基苯基 | 3.291分钟;m/z=293[M+H]+ |
324 | 3-甲基苯基 | H | CH2CH3 | H | 苯基 | 3.357分钟;m/z=293[M+H]+ |
325 | 3-甲基苯基 | H | CH3 | H | 4-甲氧基苯基 | 3.106分钟;m/z=309[M+H]+ |
326 | 3-甲基苯基 | H | H | H | 3-氟苯基 | 2.980分钟;m/z=283[M+H]+ |
327 | 3-甲基苯基 | H | CH3 | H | 4-氟苯基 | 3.460分钟;m/z=297[M+H]+ |
328 | 4-甲基苯基 | H | CH3 | H | 2-甲基苯基 | 3.239分钟;m/z=293[M+H]+ |
329 | 4-甲基苯基 | H | H | H | 3-氟苯基 | 2.958分钟;m/z=283[M+H]+ |
330 | 4-甲基苯基 | H | H | H | 2-氟苯基 | 2.966分钟;m/z=283[M+H]+ |
331 | 4-甲基苯基 | H | Cl | H | 苯基 | 3.084分钟;m/z=299[M+H]+ |
332 | 2-溴苯基 | H | CH3 | H | 3-氟苯基 | 3.529分钟;m/z=361[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
333 | 4-溴苯基 | H | CH3 | H | 4-氟苯基 | 3.618分钟;m/z=363[M+H]+ |
334 | 2-氯苯基 | H | CH3 | H | 苯基 | 3.125分钟;m/z=299[M+H]+ |
335 | 2-氯苯基 | H | CH3 | H | 4-氟苯基 | 3.478分钟;m/z=317[M+H]+ |
336 | 2-氯苯基 | H | CH3 | H | 3-氟苯基 | 3.498分钟;m/z=317[M+H]+ |
337 | 3-氯苯基 | H | Br | H | 苯基 | 3.273分钟;m/z=365[M+H]+ |
338 | 2,5-二氯苯基 | H | CH3 | H | 3-氟苯基 | 3.818分钟;m/z=351[M+H]+ |
339 | 3,5-二氯苯基 | H | CH3 | H | 4-氟苯基 | 3.930分钟;m/z=351[M+H]+ |
340 | 2-氯-5-溴苯基 | H | Cl | H | 苯基 | 3.349分钟;m/z=399[M+H]+ |
341 | 2-氟苯基 | H | H | H | 3,5-二氯苯基 | 3.718分钟;m/z=337[M+H]+ |
342 | 2-氟苯基 | H | CH3 | H | 4-叔丁基苯基 | 4.151分钟;m/z=339[M+H]+ |
343 | 2-氟苯基 | H | CH3 | H | 4-甲氧基苯基 | 3.254分钟;m/z=313[M+H]+ |
344 | 2-氟苯基 | H | H | H | 3-氟苯基 | 3.072分钟;m/z=287[M+H]+ |
345 | 3-氟苯基 | H | CH3 | H | 2,4-二氯苯基 | 3.888分钟;m/z=351[M+H]+ |
346 | 3-氟苯基 | H | H | H | 3-氟苯基 | 3.150分钟;m/z=287[M+H]+ |
347 | 3-氟苯基 | H | CH3 | H | 4-氟苯基 | 3.376分钟;m/z=301[M+H]+ |
348 | 3-氟-4-甲基苯基 | H | CH3 | H | 4-氟苯基 | 3.536分钟;m/z=315[M+H]+ |
349 | 3-氟-4-甲基苯基 | H | CH3 | H | 3-氟苯基 | 3.554分钟;m/z=315[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
350 | 3-氟-4-甲基苯基 | H | CH2CH3 | H | 苯基 | 3.756分钟;m/z=311[M+H]+ |
351 | 3-氟-4-甲基苯基 | H | CH3 | H | 4-叔丁基苯基 | 4.184分钟;m/z=353[M+H]+ |
352 | 3,4-二氟苯基 | H | CH3 | H | 3-氟苯基 | 3.476分钟;m/z=319[M+H]+ |
353 | 2,5-二氟苯基 | H | Br | H | 苯基 | 3.432分钟;m/z=365[M+H]+ |
354 | 2,5-二氟苯基 | H | CH3 | H | 1,3-苯并间二氧杂环戊烯-5-基 | 3.289分钟;m/z=345[M+H]+ |
355 | 2,5-二氟苯基 | H | H | H | 3,5-二氯苯基 | 3.758分钟;m/z=355[M+H]+ |
356 | 2,5-二氟苯基 | H | H | H | 4-氰基苯基 | 2.886分钟;m/z=312[M+H]+ |
357 | 2,6-二氟苯基 | H | CH3 | H | 4-硝基苯基 | 3.299分钟;m/z=346[M+H]+ |
358 | 2,6-二氟苯基 | H | CH3 | H | 4-氯苯基 | 3.746分钟;m/z=335[M+H]+ |
359 | 4-氟苯基 | H | Cl | H | 苯基 | 3.308分钟;m/z=303[M+H]+ |
360 | 4-氟苯基 | H | H | H | 苯基 | 3.012分钟;m/z=269[M+H]+ |
361 | 4-氟苯基 | H | CH3 | H | 4-氯苯基 | 3.656分钟;m/z=317[M+H]+ |
362 | 4-氟苯基 | H | H | H | 4-氰基苯基 | 2.877分钟;m/z=294[M+H]+ |
363 | 4-氟苯基 | H | CH3 | H | 3-氟苯基 | 3.356分钟;m/z=301[M+H]+ |
364 | 2-硝基苯基 | H | CH3 | H | 3-氟苯基 | 3.462分钟;m/z=328[M+H]+ |
365 | 3-硝基苯基 | H | CH3 | H | 3-氟苯基 | 3.434分钟;m/z=328[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
366 | 4-硝基苯基 | H | CH3 | H | 3-氟苯基 | 3.410分钟;m/z=328[M+H]+ |
367 | 3-甲基-4-硝基苯基 | H | CH3 | H | 4-氟苯基 | 3.547分钟;m/z=342[M+H]+ |
368 | 2-甲氧基苯基 | H | Cl | H | 苯基 | 3.064分钟;m/z=315[M+H]+ |
369 | 2-甲氧基苯基 | H | CH3 | H | 苯基 | 3.064分钟;m/z=295[M+H]+ |
370 | 3-甲氧基苯基 | H | Cl | H | 苯基 | 2.702分钟;m/z=315[M+H]+ |
371 | 3-甲氧基苯基 | H | CH3 | H | 苯基 | 2.720分钟;m/z=295[M+H]+ |
372 | 3,4-二甲氧基苯基 | H | CH3 | H | 4-氟苯基 | 3.143分钟;m/z=343[M+H]+ |
373 | 3-三氟甲基苯基 | H | CH2CH3 | H | 苯基 | 3.573分钟;m/z=347[M+H]+ |
374 | 3-三氟甲基苯基 | H | CH3 | H | 3-氟苯基 | 3.777分钟;m/z=351[M+H]+ |
375 | 3,5-二(三氟甲基)苯基 | H | CH3 | H | 4-氟苯基 | 4.205分钟;m/z=419[M+H]+ |
376 | 3,5-二(三氟甲基)苯基 | H | CH3 | H | 3-氟苯基 | 4.215分钟;m/z=419[M+H]+ |
377 | 4-氯苯基 | H | Cl | H | 苯基 | 3.195分钟;m/z=319[M+H]+ |
378 | 4-氯苯基 | H | CH3 | H | 苯基 | 3.190分钟;m/z=299[M+H]+ |
379 | 3,5-二氯苯基 | H | CH3 | H | 2-甲基苯基 | 4.052分钟;m/z=347[M+H]+ |
380 | 3,5-二氯苯基 | H | CH3 | H | 苯基 | 3.888分钟;m/z=333[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
381 | 3,5-二氯苯基 | H | Cl | H | 苯基 | 3.921分钟;m/z=353[M+H]+ |
382 | 4-乙氧基苯基 | H | Cl | H | 苯基 | 3.128分钟;m/z=329[M+H]+ |
383 | 3-羟基苯基 | H | CH3 | H | 4-氟苯基 | 2.936分钟;m/z=299[M+H]+ |
384 | 3-羟基苯基 | H | CH3 | H | 3-氟苯基 | 2.949分钟;m/z=299[M+H]+ |
385 | 4-羟基苯基 | H | CH3 | H | 3-氟苯基 | 2.912分钟;m/z=299[M+H]+ |
386 | 3-羟基-2-萘基 | H | H | H | 2-氟苯基 | 3.198分钟;m/z=335[M+H]+ |
387 | 2-甲氧基-4-甲硫基苯基 | H | CH3 | H | 4-氟苯基 | 3.652分钟;m/z=359[M+H]+ |
388 | 2-甲氧基-4-甲硫基苯基 | H | H | H | 苯基 | 3.380分钟;m/z=327[M+H]+ |
389 | 2-甲氧基-4-甲硫基苯基 | H | CH3 | H | 4-氯苯基 | 3.890分钟;m/z=375[M+H]+ |
390 | 2-甲氧基-4-甲硫基苯基 | H | H | H | 3-氟苯基 | 3.448分钟;m/z=345[M+H]+ |
391 | 2-甲氧基-4-甲硫基苯基 | H | H | H | 2-氟苯基 | 3.473分钟;m/z=345[M+H]+ |
392 | 吡啶-2-基 | H | CH2CH3 | H | 2-氟苯基 | 3.275分钟;m/z=298[M+H]+ |
实施例号 | Ar | R1 | R2 | R3 | R4 | 熔点或RT(HPLC/MS)) |
393 | 吡啶-2-基 | H | CH2CH3 | H | 4-氟苯基 | 3.273分钟;m/z=298[M+H]+ |
394 | 6-甲基吡啶-2-基 | H | CH2CH3 | H | 2-氟苯基 | 3.502分钟;m/z=312[M+H]+ |
395 | 6-甲基吡啶-2-基 | H | CH2CH3 | H | 2,3-二氟苯基 | 3.577分钟;m/z=330[M+H]+ |
396 | 6-溴吡啶-2-基 | H | CH2CH3 | H | 4-氟苯基 | 3.680分钟;m/z=378[M+H]+ |
397 | 6-氯吡啶-2-基 | H | CH3 | H | 3-氟苯基 | 3.398分钟;m/z=318[M+H]+ |
398 | 3-氟吡啶-2-基 | H | CH3 | H | 苯基 | 2.938分钟;m/z=284[M+H]+ |
399 | 3-氟吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 2.998分钟;m/z=302[M+H]+ |
400 | 6-氟吡啶-2-基 | H | CH3 | H | 苯基 | 3.165分钟;m/z=284[M+H]+ |
401 | 6-氟吡啶-2-基 | H | CH3 | H | 4-氟苯基 | 3.212分钟;m/z=302[M+H]+ |
表4
实施例号 | Ar | n | X | Z | R3 | R5 | 熔点或RT*(HPLC/MS)或δ(1H NMR) |
402 | 5-氯噻吩-2-基 | 0 | SO2 | O | H | H | 128-130℃ |
403 | 2,5-二氯噻吩-3-基 | 0 | SO2 | O | H | H | 152-154℃ |
404 | 4-溴-2,5-二氯噻吩-3-基 | 0 | SO2 | O | H | H | 154-155℃ |
405 | 噻吩-2-基 | 1 | CO | O | H | H | |
406 | 噻吩-3-基 | 1 | CO | O | H | H | 154-155℃ |
407 | 苯基 | 1 | CO | O | H | H | 3.232分钟;m/z=279[M+H]+ |
408 | 3,4-二甲氧基苯基 | 1 | CO | O | H | H | 3.015分钟;m/z=339[M+H]+ |
409 | 3,4-二甲氧基苯基 | 1 | CO | S | H | H | 3.295分钟;m/z=355[M+H]+ |
410 | 1-萘基 | 1 | CO | O | H | H | 3.639分钟;m/z=329[M+H]+ |
411 | 吲哚-3-基 | 1 | CO | S | H | H | 3.341分钟;m/z=334[M+H]+ |
412 | 噻吩-2-基 | 0 | CO | O | H | H | |
413 | 噻吩-2-基 | 0 | CO | CH2O | Cl | Cl |
实施例号 | Ar | n | X | Z | R3 | R5 | 熔点或RT*(HPLC/MS)或δ(1H NMR) |
414 | 噻吩-2-基 | 0 | CO | S | CH3 | H | 240-242℃ |
415 | 噻吩-2-基 | 0 | CO | S | H | H | 3.375分钟;m/z=287[M+H]+ |
416 | 噻吩-2-基 | 0 | CO | O | H | H | 3.078分钟;m/z=271[M+H]+ |
417 | 3-甲基噻吩-2-基 | 0 | CO | O | H | H | 174-176℃ |
418 | 5-甲基噻吩-2-基 | 0 | CO | O | H | H | 209-212℃ |
419 | 5-甲基噻吩-2-基 | 0 | CO | O | Cl | H | 211-212℃ |
420 | 5-氯噻吩-2-基 | 0 | CO | O | H | H | 205-206℃ |
421 | 5-溴噻吩-2-基 | 0 | CO | O | H | H | 232-234℃ |
422 | 5-溴噻吩-2-基 | 0 | CO | O | Cl | H | 236-237℃ |
423 | 3-氯-4-甲基噻吩-2-基 | 0 | CO | O | H | H | 234-237℃ |
424 | 3-氯-4-甲基噻吩-2-基 | 0 | CO | O | Cl | H | 208℃ |
425 | 苯并噻吩-2-基 | 0 | CO | O | H | H | 3.577分钟;m/z=321[M+H]+ |
426 | 苯并噻吩-2-基 | 0 | CO | S | H | H | 3.916分钟;m/z=337[M+H]+ |
427 | 3-乙氧基噻吩-2-基 | 0 | CO | O | H | H | 180-182℃ |
428 | 呋喃-2-基 | 0 | CO | S | H | H | 2.906分钟;m/z=271[M+H]+ |
429 | 呋喃-2-基 | 0 | CO | O | H | H | 2.661分钟;m/z=255[M+H]+ |
430 | 异唑-5-基 | 0 | CO | O | H | H |
实施例号 | Ar | n | X | Z | R3 | R5 | 熔点或RT*(HPLC/MS)或δ(1H NMR) |
431 | 4-甲基咪唑-5-基 | 0 | CO | O | H | H | 2.077分钟;m/z=269[M+H]+ |
432 | 1,5-二甲基吡唑-3-基 | 0 | CO | O | H | H | |
433 | 1,3-二甲基吡唑-5-基 | 0 | CO | O | H | H | |
434 | 4-氯-1,3-二甲基吡唑-5-基 | 0 | CO | O | H | H | 172-174℃ |
435 | 吡啶-2-基 | 0 | CO | O | H | H | 3.799分钟;m/z=266[M+H]+ |
436 | 吡啶-2-基 | 0 | CO | S | H | H | 3.044分钟;m/z=282[M+H]+ |
437 | 吡啶-3-基 | 0 | CO | O | H | H | 2.095分钟;m/z=266[M+H]+ |
438 | 2-苯氧基吡啶-3-基 | 0 | CO | O | H | H | 3.342分钟;m/z=358[M+H]+ |
439 | 吡啶-4-基 | 0 | CO | S | H | H | 2.305分钟;m/z=282[M+H]+ |
440 | 吡啶-4-基 | 0 | CO | O | H | H | 2.090分钟;m/z=266[M+H]+ |
441 | 2-氯吡啶-4-基 | 0 | CO | O | H | H | 230-231℃ |
442 | 吡嗪-2-基 | 0 | CO | O | H | H | |
443 | 二苯并-4H-吡喃-4-基 | 0 | CO | O | H | H | 3.786分钟;m/z=369[M+H]+ |
444 | 苯基 | 0 | CO | O | H | H | 2.913分钟;m/z=265[M+H]+ |
445 | 3-甲基苯基 | 0 | CO | O | H | H | 3.155分钟;m/z=279[M+H]+ |
实施例号 | Ar | n | X | Z | R3 | R5 | 熔点或RT*(HPLC/MS)或δ(1H NMR) |
446 | 4-甲基苯基 | 0 | CO | O | H | H | 3.129分钟;m/z=279[M+H]+ |
447 | 2-甲氧基苯基 | 0 | CO | O | H | H | 3.122分钟;m/z=295[M+H]+ |
448 | 3-甲氧基苯基 | 0 | CO | S | H | H | 3.233分钟;m/z=311[M+H]+ |
449 | 3-甲氧基苯基 | 0 | CO | O | H | H | 3.001分钟;m/z=295[M+H]+ |
450 | 2-氟苯基 | 0 | CO | O | H | H | 2.979分钟;m/z=283[M+H]+ |
451 | 2,5-二氟苯基 | 0 | CO | O | H | H | 3.095分钟;m/z=301[M+H]+ |
452 | 3-氟-4-甲基苯基 | 0 | CO | O | H | H | 3.250分钟;m/z=297[M+H]+ |
453 | 3-溴苯基 | 0 | CO | O | H | H | 3.345分钟;m/z=344[M+H]+ |
454 | 3-甲基苯基 | 0 | CO | S | H | H | 3.369分钟;m/z=295[M+H]+ |
455 | 2-硝基苯基 | 0 | CO | S | H | H | 3.256分钟;m/z=326[M+H]+ |
456 | 4-三氟甲基苯基 | 0 | CO | S | H | H | 3.657分钟;m/z=349[M+H]+ |
457 | 3-溴苯基 | 0 | CO | S | H | H | 3.560分钟;m/z=361[M+H]+ |
458 | 2-氯苯基 | 0 | CO | S | H | H | 3.352分钟;m/z=315[M+H]+ |
459 | 2,5-二氯苯基 | 0 | CO | S | H | H | 3.705分钟;m/z=349[M+H]+ |
460 | 2-甲氧基苯基 | 0 | CO | S | H | H | 3.424分钟;m/z=311[M+H]+ |
461 | 3,4,5-三甲氧基苯基 | 0 | CO | S | H | H | 3.241分钟;m/z=371[M+H]+ |
462 | 3,4-二甲氧基苯基 | 0 | CO | S | H | H | 3.082分钟;m/z=341[M+H]+ |
实施例号 | Ar | n | X | Z | R3 | R5 | 熔点或RT*(HPLC/MS)或δ(1H NMR) |
463 | 3,5-二(三氟甲基)苯基 | 0 | CO | S | H | H | 4.119分钟;m/z=417[M+H]+ |
464 | 3-甲基-4-硝基苯基 | 0 | CO | S | H | H | 3.477分钟;m/z=340[M+H]+ |
465 | 苯基 | 0 | CO | S | H | H | 3.169分钟;m/z=281[M+H]+ |
466 | 4-羟基苯基 | 0 | CO | S | H | H | 2.801分钟;m/z=297[M+H]+ |
467 | 2-氟苯基 | 0 | CO | S | H | H | 3.225分钟;m/z=299[M+H]+ |
468 | 2,5-二氟苯基 | 0 | CO | S | H | H | 3.339分钟;m/z=317[M+H]+ |
469 | 2-甲氧基-4-甲硫基苯基 | 0 | CO | S | H | H | 3.587分钟;m/z=357[M+H]+ |
470 | 3,4-二氟苯基 | 0 | CO | S | H | H | 3.380分钟;m/z=317[M+H]+ |
471 | 3-羟基-2-萘基 | 0 | CO | O | H | H | 3.471分钟;m/z=331[M+H]+ |
472 | 4-苯基苯基 | 0 | CO | O | H | H | 3.610分钟;m/z=341[M+H]+ |
473 | 2-溴苯基 | 0 | CO | O | H | H | 3.162分钟;m/z=343[M+H]+ |
474 | 2-萘基 | 0 | CO | O | H | H | 3.402分钟;m/z=315[M+H]+ |
475 | 4-溴苯基 | 0 | CO | O | H | H | 3.317分钟;m/z=345[M+H]+ |
476 | 4-氯苯基 | 0 | CO | O | H | H | 3.253分钟;m/z=299[M+H]+ |
477 | 2-氯苯基 | 0 | CO | O | H | H | 3.112分钟;m/z=299[M+H]+ |
478 | 2,5-二氯苯基 | 0 | CO | O | H | H | 3.436分钟;m/z=333[M+H]+ |
479 | 4-叔丁基苯基 | 0 | CO | O | H | H | 3.707分钟;m/z=321[M+H]+ |
实施例号 | Ar | n | X | Z | R3 | R5 | 熔点或RT*(HPLC/MS)或δ(1H NMR) |
480 | 3,4-二甲氧基苯基 | 0 | CO | O | H | H | 2.858分钟;m/z=325[M+H]+ |
481 | 4-甲氧基苯基 | 0 | CO | O | H | H | 2.980分钟;m/z=295[M+H]+ |
482 | 2,4-二氯苯基 | 0 | CO | O | H | H | 3.459分钟;m/z=333[M+H]+ |
483 | 3-三氟甲基苯基 | 0 | CO | O | H | H | 3.479分钟;m/z=333[M+H]+ |
484 | 4-氟苯基 | 0 | CO | O | H | H | 2.999分钟;m/z=283[M+H]+ |
485 | 3-氟苯基 | 0 | CO | O | H | H | 3.037分钟;m/z=283[M+H]+ |
486 | 2,6-二氟苯基 | 0 | CO | O | H | H | 3.075分钟;m/z=301[M+H]+ |
487 | 3,5-二氯苯基 | 0 | CO | O | H | H | 3.631分钟;m/z=333[M+H]+ |
488 | 2-甲氧基-4-甲硫基苯基 | 0 | CO | O | H | H | 3.400分钟;m/z=341[M+H]+ |
489 | 3-甲氧基噻吩-2-基 | 0 | CO | O | H | H | 2.897分钟;m/z=301[M+H]+ |
490 | 4-三氟甲基吡啶-3-基 | 0 | CO | NMe | H | H | 3.082分钟;m/z=347[M+H]+ |
*RT=保留时间HPLC/MS
2.对害虫的作用实施例
式I化合物对害虫的作用通过下列试验证实。
2.1亚热带粘虫(即南部灰翅夜蛾(Spodoptera eridania)),二龄幼虫
为了测试对昆虫和蜘蛛的活性,将活性化合物配制成在35%丙酮和水的混合物中的10.000ppm溶液,需要的话,用水稀释该溶液。
在搅拌下将生长至长7-8cm的菜豆(Sieva lima bean)叶子浸入搅动的试验溶液中3秒钟并在通风橱中干燥。然后将叶子放入含有位于底部上的潮湿滤纸和10只二龄幼虫的100×10mm陪替氏培养皿中。在5天内观察死亡率、进食减退或任何正常换羽干扰。
在该测试中,与未处理对照相比,化合物18、97、101、134、160、161、162、164、166、174、175、177、183、185、190、192、198、238、318、406、427和445在300ppm下显示出超过80%的死亡率。
2.2棉蚜(即Aphis gossypii)
在50∶50丙酮∶水和100ppm Kinetic®表面活性剂中配制活性化合物。
通过将来自主群体的严重侵染的叶子放于各子叶的顶部而侵染子叶阶段的棉花植物(每盆一棵植株)。使蚜虫在一夜内转移到寄主植株上并取出用于转移蚜虫的叶子。将子叶浸于测试溶液中并干燥。5天后统计死亡率。
在该测试中,与未处理对照相比,化合物8、67、70、71、120、121、126、130、131、156、157、159、181、194、202、203、207、236、240、277、314、319、392、394、395、398、399、429、442、444、447、450和451在300ppm下显示出超过75%的死亡率。
2.3桃蚜(即Myzus persicae)
在50∶50丙酮∶水和100ppm Kinetic®表面活性剂中配制活性化合物。
通过将侵染的叶片放于测试植物顶部而将第二对叶阶段的胡椒植物(品种为“California Wonder”)用约40只实验室饲养的蚜虫侵染。在24小时后取出叶片。将整棵植物的叶子浸入测试化合物的梯度溶液中并干燥。将测试植物在约25℃和20-40%相对湿度下维持在荧光(24小时光照期)下。5天后相对于对照植物上的死亡率测定处理植物上的蚜虫死亡率。
在该测试中,与未处理对照相比,化合物3、10、14、19、20、76、128、152、173、186、194、195、197、198、200、204、235、237、278、320、321、393、396、397、400、401、407、408、409、411和453在300ppm下显示出超过75%的死亡率。
2.4蚕豆蚜(即甜菜蚜(Aphis fabae))
在50∶50丙酮∶水和100ppm Kinetic®表面活性剂中配制活性化合物。
通过将侵染的所切植物放于测试植物的顶部而将生长在Metro混合物中的第一对叶阶段的旱金莲属植物(品种为“Mixed Jewle”)用约2-30只实验室饲养的蚜虫侵染。24小时后取出所切植物。将各植物浸入测试溶液中以完全覆盖叶面、茎、突出的种子表面和周围的立方体表面并在烟橱中干燥。将处理植物在连续荧光下保持在约25℃。3天后测定蚜虫死亡率。
在该测试中,与未处理对照相比,化合物18、69、71、126、157、159、168、169、170、171、184、191、196、199、202、210、253、436、442、444和446在300ppm下显示出超过75%的死亡率。
2.5银叶粉虱(即Bemisia argentifolii)
在50∶50丙酮∶水和100ppm Kinetic®表面活性剂中配制活性化合物。
使选取的棉花植物生长到子叶阶段(每盆一棵植株)。将子叶浸入测试溶液中以完全覆盖叶面并放于良好通风的区域以进行干燥。将具有处理秧苗的各盆放入塑料杯中并引入10-12只银叶粉虱成虫(约3-5天龄)。使用呼吸器和连接于防渗移液管尖端的0.6cm无毒Tygon®管(R-3603)收集昆虫。然后将含有收集的昆虫的该尖端轻轻地插入含有处理植物的土壤中,使昆虫爬出该尖端而到达叶面上取食。将杯子用可再用的筛盖(150微米网眼的聚酯筛PeCap,购自Tetko Inc)覆盖。将测试植物在保持室中于约25℃和20-40%相对湿度下保持3天,并避免直接暴露于荧光(24小时光照期)以防止在杯子内蓄积热。在处理植物3天后评价死亡率。
在该测试中,与未处理对照相比,化合物2、6、50、156、158、175、183、187、189、193、406和435在300ppm下显示出超过80%的死亡率。
2.6二斑叶螨(即二点叶螨(Tetranychus urticae),耐OP的品系)
在50∶50丙酮∶水和100ppm Kinetic®表面活性剂中配制活性化合物。
通过在各植物上放置一小片取自主群体的侵染叶子(含约100只螨虫)而将主叶生长至7-12cm的菜豆(Sieva lima bean)植物侵染。这在处理之前约2小时进行以使螨虫移到测试植物上产卵。取出用于转移螨虫的叶片。将新侵染的植物浸入测试溶液中并干燥。将测试植物在约25℃和20-40%相对湿度下保持在荧光(24小时光照期)下。5天后取出一片叶并统计死亡率。
在该测试中,与未处理对照相比,化合物21、91、96、114、138、183、429和452在300ppm下显示出超过75%的死亡率。
2.7兰蓟马(即Dichromothrips corbetti)
用于生物评价的兰蓟马成虫由连续维持在实验室条件下的群体得到。为了进行测试,将试验化合物在丙酮∶水的1∶1混合物(加有0.01% Kinetic®表面活性剂)中稀释到浓度为500ppm(化合物重量∶稀释剂体积)。
各化合物的蓟马防治效力通过使用花浸渍技术进行评价。将塑料陪替氏培养皿用作测试器。将各完整兰花的所有花瓣浸入处理溶液中约3秒钟并干燥2小时。将处理过的花与10-15只蓟马成虫一起放入各培养皿中。然后用盖子覆盖培养皿。将所有测试器保持在连续光照和约28℃的温度下以持续进行评价。4天后在各花上以及各培养皿的内壁上统计活蓟马数目。由预处理蓟马数目外推蓟马死亡率水平。
在该测试中,与未处理对照相比,化合物103、105和144在500ppm下显示出超过95%的死亡率。
Claims (21)
1.一种防治昆虫或蜘蛛的方法,包括使昆虫或蜘蛛,其栖息地,繁殖地,食物源,其中昆虫或蜘蛛生长或可能生长的植物、种子、土壤、区域、材料或环境或需要防止昆虫或蜘蛛侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的通式I化合物或其盐接触:
其中:
Ar为选自如下的环状基团:苯基,萘基和具有1-4个相互独立地选自O、N和S的杂原子的5或6元杂环基团,其中该5或6元杂环基团可以与1或2个苯环稠合,其中该环状基团可以具有1、2、3、4或5个取代基Ra,所述取代基Ra相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基、R5R6N-CO-、苯基、苄基和苯氧基,其中苯基、苄基和苯氧基可以被1、2、3、4或5个取代基Rb取代,所述取代基Rb相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO-;
X为CO或SO2;
R1为H、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C2-C10卤代炔基或可以被1-5个取代基取代的苯基,所述取代基相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO-;
R2和R3相互独立地为H、卤素、氰基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、羟基-C1-C10烷基、C1-C10烷氧基-C1-C10烷基、卤代-C1-C10烷氧基-C1-C10烷基、C1-C10烷氧羰基-C1-C10烷基、卤代-C1-C10烷氧羰基-C1-C10烷基或可以被1-5个取代基取代的苯基,所述取代基相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO;
R4为选自苯基、吡啶基、嘧啶基或呋喃基、噻吩基的芳族基团,其中芳族基团可以带有1-5个取代基Rb,所述取代基Rb相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基、R5R6N-CO-和可以被1-5个取代基取代的苯氧基,所述取代基相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO;或
R2和R4与它们所连接的碳原子一起形成苯环或具有1或2个相互独立地选自O、N和S的杂原子的5或6元杂环,其中苯环和5或6元杂环可以与苯环稠合且苯环和5或6元杂环和/或它们所稠合的苯环可以带有1、2、3或4个取代基Re,所述取代基Re相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C2-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C2-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基、R5R6N-CO和可以被1、2、3、4或5个取代基Rf取代的苯氧基,所述取代基Rf相互独立地选自卤素、氰基、硝基、C1-C10烷基、C1-C10卤代烷基、C3-C10环烷基、C3-C10卤代环烷基、C2-C10链烯基、C2-C10卤代链烯基、C2-C10炔基、C3-C10卤代炔基、C1-C10烷氧基、C1-C10卤代烷氧基、C2-C10链烯氧基、C2-C10卤代链烯氧基、C2-C10炔氧基、C3-C10卤代炔氧基、C1-C10烷硫基、C1-C10卤代烷硫基、C1-C10烷基亚磺酰基、C1-C10卤代烷基亚磺酰基、C1-C10烷基磺酰基、C1-C10卤代烷基磺酰基、羟基、NR5R6、C1-C10烷氧羰基、C1-C10卤代烷氧羰基、C2-C10链烯氧羰基、C2-C10卤代链烯氧羰基、C1-C10烷基羰基、C1-C10卤代烷基羰基和R5R6N-CO,且其中5或6元杂环可以含有1个羰基作为环成员;
R5和R6相互独立地为H或C1-C10烷基;和
n为0或1。
2.如权利要求1所要求的方法,其中,
Ar为选自如下的环状基团:苯基、萘基和具有1-3个相互独立地选自O、N和S的杂原子的5或6元杂环基团,其中该5或6元杂环基团可以与1或2个苯环稠合且其中该环状基团可以具有1、2、3或4个取代基Ra,所述取代基Ra相互独立地选自卤素、羟基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、未被取代或被1-3个相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基和C1-C4烷氧基的取代基Rb取代的苯基或未被取代或被1-3个相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基和C1-C4烷氧基的取代基Rb取代的苯氧基。
3.如权利要求2所要求的方法,其中:
Ar为选自如下的环状基团:噻吩基、呋喃基、吡唑基、咪唑基、异噁唑基、噻唑基、噻二唑基、苯基、吡啶基、吡嗪基、萘基、二苯并吡喃基、吲哚基或苯并噻吩基,且其中该环状基团可以被1、2或3个取代基Ra取代,所述取代基Ra相互独立地选自卤素,羟基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基,未被取代或被1、2或3个相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基和C1-C4烷氧基的取代基Rb取代的苯基以及未被取代或被1、2或3个相互独立地选自卤素、C1-C4烷基、C1-C4烷氧基和C1-C4卤代烷基的取代基Rb取代的苯氧基。
4.如权利要求3所要求的方法,其中:
Ar为选自如下的环状基团:噻吩基、呋喃基、吡唑基、咪唑基、异噁唑基、苯基、吡啶基、吡嗪基、萘基、吲哚基或苯并噻吩基,且其中该环状基团可以被1或2个相互独立地选自卤素、羟基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和C1-C4卤代烷氧基的取代基Ra取代。
5.如前述权利要求中任一项所要求的方法,其中R1为H、C1-C4烷基或C1-C4卤代烷基。
6.如权利要求5所要求的方法,其中R1为H或甲基。
7.如前述权利要求中任一项所要求的方法,其中:
R2和R4与它们所连接的碳原子一起形成苯环或具有1或2个相互独立地选自O、N和S的杂原子的5或6元杂环,其中该5或6元杂环可以与苯环稠合且该5或6元杂环和/或其所稠合的苯环可以带有1、2、3或4个取代基Re,所述取代基Re相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、氰基、硝基、未被取代或被1、2或3个相互独立地选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和卤素的取代基取代的苯基;以及未被取代或被1、2或3个取代基Rf取代的苯氧基,所述取代基Rf相互独立地选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和卤素,以及其中该5或6元杂环可以含有1个羰基作为环成员。
8.如权利要求7所要求的方法,其中:
R2和R4与它们所连接的碳原子一起形成苯基、苯并呋喃基、苯并噻吩基、吲哚基、苯并吡喃基、苯并-γ-吡喃酮基、吡唑基或呋喃基结构部分,且其中该结构部分可以带有1、2、3或4个相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、氰基和硝基的取代基Re。
9.如权利要求8所要求的方法,其中:
R2和R4与它们所连接的碳原子一起形成苯基、苯并呋喃基、苯并噻吩基或苯并吡喃基结构部分且该结构部分可以被1、2或3个相互独立地选自C1-C4烷基、C1-C4卤代烷基和卤素的取代基Re取代。
10.如权利要求1-6中任一项所要求的方法,其中R2为H、C1-C10烷基、C1-C10卤代烷基、卤素、苯基或氰基。
11.如权利要求1-6和10中任一项所要求的方法,其中R3为H、C1-C4烷基、卤素或苯基。
12.如权利要求1-6、10和11中任一项所要求的方法,其中:
R4为选自苯基、吡啶基、嘧啶基、呋喃基或噻吩基的芳族基团,其中该芳族基团可以带有1、2、3、4或5个相互独立地选自羟基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氰基、硝基、NR5R6和可以被C1-C4卤代烷基取代的苯氧基的取代基Rc;和
R5和Rb如权利要求1所定义。
13.如权利要求12所要求的方法,其中:
R4为可以带有1、2、3、4或5个相互独立地选自羟基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氰基、硝基、NR5R6和可以被C1-C4卤代烷基取代的苯氧基的取代基Rc的苯基。
14.如权利要求1-6和10-12中任一项所要求的方法,其中:
R2为H、C1-C10烷基、C1-C10卤代烷基、卤素、苯基或氰基;
R3为H、C1-C4烷基、卤素或苯基;和
R4为选自苯基、吡啶基、嘧啶基、呋喃基或噻吩基的芳族基团,其中该芳族基团可以带有1、2、3或4个相互独立地选自羟基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氰基、硝基、NR5R6和可以被C1-C4卤代烷基取代的苯氧基的取代基Rc;和
R5和R6如权利要求1所定义。
15.如权利要求14所要求的方法,其中
R4为可以带有1、2、3或4个相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氰基、硝基、NR5R6和可以被C1-C4卤代烷基取代的苯氧基的取代基Rc的苯基。
16.如权利要求14或15所要求的方法,其中:
R2为H、C1-C10烷基或卤素;
R3为H或卤素;和
R4为可以带有1、2或3个相互独立地选自卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、氰基和硝基的取代基Rc的苯基。
17.一种保护作物以防止昆虫或蜘蛛侵袭或侵染的方法,包括使作物与杀虫有效量的如权利要求1所定义的式I化合物接触。
18.如权利要求17所要求的方法,其中式I化合物的施用率为0.1-4000g/ha。
19.通式Ia的吡啶基化合物:
其中Ra、R1和R3如权利要求1所定义,
m为0、1、2或3,
R2a为C1-C4烷基,和
R4a为可以带有1、2、3或4个如权利要求1所定义的基团Rc的苯基,条件是:
i)m不为0,或
ii)R4a带有至少一个不为氢的取代基Rc,或
iii)R1不为氢,或
iv)R2a不为甲基。
20.式Ib的异噁唑基化合物:
其中n、X、R1、R2、R3和R4如权利要求1所定义,
Ar为可以带有1或2个如权利要求1所定义的取代基Ra的异噁唑基,条件是若Ar为取代的4-异噁唑基,则Ar不带有任选取代的苯基。
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103641782A (zh) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | 一种吡唑酰腙类化合物及其应用 |
CN109071437A (zh) * | 2016-02-19 | 2018-12-21 | 韩国生命工学研究院 | 新型吲哚衍生物和包含其的抗癌组合物 |
CN110627692A (zh) * | 2019-10-14 | 2019-12-31 | 河南科技大学 | 丹皮酚苯磺酰腙及其衍生物和其制备方法、植物源杀虫剂及其应用 |
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WO2012051708A1 (en) * | 2010-10-21 | 2012-04-26 | The University Of British Columbia | Anti-bacterial pyruvate kinase modulator compounds, compositions, uses, and methods |
KR101565430B1 (ko) | 2012-09-07 | 2015-11-03 | 한국생명공학연구원 | N-메틸렌나프토[2,1-b]퓨란-2-카보하이드라지드 유도체를 유효성분으로 포함하는 암 예방 또는 치료용 조성물 |
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GB9716446D0 (en) * | 1997-08-05 | 1997-10-08 | Agrevo Uk Ltd | Fungicides |
JP2000169461A (ja) * | 1998-09-28 | 2000-06-20 | Nippon Nohyaku Co Ltd | 殺虫殺菌剤組成物及びその使用方法 |
JP2004149413A (ja) * | 2000-06-30 | 2004-05-27 | Agro Kanesho Co Ltd | 有害生物の防除に有効なヒドラゾン誘導体又はその塩 |
-
2004
- 2004-05-26 BR BRPI0410626-1A patent/BRPI0410626A/pt not_active IP Right Cessation
- 2004-05-26 KR KR1020057022609A patent/KR20060019558A/ko not_active Application Discontinuation
- 2004-05-26 AU AU2004243492A patent/AU2004243492A1/en not_active Abandoned
- 2004-05-26 EP EP04734834A patent/EP1631143A1/en not_active Withdrawn
- 2004-05-26 WO PCT/EP2004/005681 patent/WO2004105488A1/en active Search and Examination
- 2004-05-26 JP JP2006529926A patent/JP2006528955A/ja not_active Withdrawn
- 2004-05-26 MX MXPA05012226A patent/MXPA05012226A/es not_active Application Discontinuation
- 2004-05-26 AR ARP040101810A patent/AR045688A1/es unknown
- 2004-05-26 CN CNA2004800146224A patent/CN1842272A/zh active Pending
- 2004-05-27 CL CL200401296A patent/CL2004001296A1/es unknown
-
2005
- 2005-12-22 ZA ZA200510406A patent/ZA200510406B/xx unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103641782A (zh) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | 一种吡唑酰腙类化合物及其应用 |
CN109071437A (zh) * | 2016-02-19 | 2018-12-21 | 韩国生命工学研究院 | 新型吲哚衍生物和包含其的抗癌组合物 |
CN109071437B (zh) * | 2016-02-19 | 2021-12-10 | 韩国生命工学研究院 | 新型吲哚衍生物和包含其的抗癌组合物 |
CN110627692A (zh) * | 2019-10-14 | 2019-12-31 | 河南科技大学 | 丹皮酚苯磺酰腙及其衍生物和其制备方法、植物源杀虫剂及其应用 |
CN110627692B (zh) * | 2019-10-14 | 2021-09-24 | 河南科技大学 | 丹皮酚苯磺酰腙及其衍生物和其制备方法、植物源杀虫剂及其应用 |
Also Published As
Publication number | Publication date |
---|---|
KR20060019558A (ko) | 2006-03-03 |
AU2004243492A1 (en) | 2004-12-09 |
EP1631143A1 (en) | 2006-03-08 |
ZA200510406B (en) | 2008-12-31 |
WO2004105488A1 (en) | 2004-12-09 |
AR045688A1 (es) | 2005-11-09 |
MXPA05012226A (es) | 2006-02-10 |
BRPI0410626A (pt) | 2006-06-20 |
CL2004001296A1 (es) | 2005-04-08 |
JP2006528955A (ja) | 2006-12-28 |
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