CN101687813A - 用于防治动物害虫的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物 - Google Patents
用于防治动物害虫的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物 Download PDFInfo
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- CN101687813A CN101687813A CN200880023200A CN200880023200A CN101687813A CN 101687813 A CN101687813 A CN 101687813A CN 200880023200 A CN200880023200 A CN 200880023200A CN 200880023200 A CN200880023200 A CN 200880023200A CN 101687813 A CN101687813 A CN 101687813A
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- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
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- 125000001166 thiolanyl group Chemical group 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
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- UNCRKEZQEKKGQX-UHFFFAOYSA-N trans-aconitic acid anhydride Chemical compound OC(=O)C1=CC(=O)OC(=O)C1 UNCRKEZQEKKGQX-UHFFFAOYSA-N 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
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- 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
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- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
- 208000003982 trichinellosis Diseases 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
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- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
本发明涉及可以用于防治动物害虫的式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其盐。本发明还涉及一种通过使用这些化合物防治动物害虫的方法,种子以及包含所述化合物的农用和兽用组合物,其中A为式A.1或A.2的基团,其中#表示与式I化合物的剩余部分的键,X选自O、S和NRX,R1选自-ORA、-NRB1RB2、-C(=O)-RC、-C(=O)-ORD、-C(=O)-SRE、-C(=O)-NRB1RB2′、-C(=S)-RC′、-C(=S)-ORD′、-C(=S)-SRE′、-C(=S)-NRB1RB2、-C(=NR1a)-RC′、-C(=NR1b)-ORD′、-C(=NR1c)-SRE′、-C(=NR1d)-NRB1RB2、-S(=O)-RF、-S(=O)2-RG、-S(=O)2-NRB1RB2′、-P(=O)RH1RH2、-P(=S)RH1RH2、-B-C(=O)-RI、-B-O-C(=O)-RI、-B-S-C(=O)-RI、-B-N(RJ)-C(=O)-RK、-B-C(=S)-RK、-B-O-C(=S)-RK、-B-S-C(=S)-RK、-B-N(RJ)-C(=S)-RK、C1-C8链烯基、C1-C8炔基、未被取代或可以带有1-4个取代基R1e的C3-C8环烷基、未被取代或可以带有1-4个取代基R1f的萘基、未被取代或可以带有1-4个取代基R1g的饱和或部分不饱和杂环、未被取代或可以带有1-4个取代基R1h的杂芳基和带有选自如下的基团的C1-C6烷基:-NR1iR1j、C1-C4烷氧羰基、C3-C8环烷基、芳基、芳氧基、芳硫基、杂环基、杂环氧基和杂环硫基,R2、R3、R4、R5、R6和R7各自独立地为氢、卤素、OH、SH、NH2、SO3H、COOH、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6烷基氨基等。
Description
本发明涉及用于防治动物害虫的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物。本发明还涉及一种通过使用这些化合物防治动物害虫的方法,涉及种子以及涉及包含所述化合物的农用和兽用组合物。
动物害虫,尤其是节肢动物和线虫损坏生长和收获的作物并攻击木质居住和商业结构体,从而对食物供应和财产造成大的经济损失。尽管已知大量杀虫剂,但由于目标害虫能够对所述杀虫剂产生耐药性,仍然需要用于防治昆虫、蜘蛛和线虫的新试剂。因此,本发明的目的是提供对于大量不同的动物害虫,尤其对于难以防治的昆虫、蜘蛛和线虫具有良好的杀虫活性并显示出宽活性谱的化合物。
Jennings等,Pesticide Biochemistry and Physiology 30,1988,第190-197页描述了几种具有杀虫活性的2-苯基氨基噁唑啉和2-苄基氨基噁唑啉。Biosci.Biotech.Biochem.1992,56(7),1062-1065公开了具有杀虫活性的苯基-、苄基-和苯乙基噻唑啉。然而,这些化合物的活性有限或者其活性谱的宽度有限。
WO 2005/063724描述了通式C.1和C.2的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物:
其中X为硫或氧,它们可以用于防治昆虫、蜘蛛和线虫。
本发明的目的是提供具有良好的杀虫活性,尤其是杀昆虫活性且对大量不同动物害虫,尤其对难于防治的昆虫显示出宽活性谱的化合物。
已经发现这些目的可以由下式I的化合物实现。
因此,本发明在第一方面涉及式I化合物或其对映体、非对映体或盐:
其中
A为式A.1或A.2的基团:
其中#表示与式I化合物的剩余部分的键,
X选自O、S和NRX,其中
RX选自氢、氰基、硝基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基、甲酰基、C1-C6烷基羰基和C1-C6烷氧羰基;
R1选自-ORA、-NRB1RB2,
-C(=O)-RC、-C(=O)-ORD、-C(=O)-SRE、-C(=O)-NRB1RB2′、-C(=S)-RC′、-C(=S)-ORD′、-C(=S)-SRE′、-C(=S)-NRB1RB2、-C(=NR1a)-RC′、-C(=NR1b)-ORD′、-C(=NR1c)-SRE′、-C(=NR1d)-NRB1RB2,
-S(=O)-RF、-S(=O)2-RG、-S(=O)2-NRB1RB2′、-P(=O)RH1RH2、-P(=S)RH1RH2,-B-C(=O)-RI、-B-O-C(=O)-RI、-B-S-C(=O)-RI、-B-N(RJ)-C(=O)-RK、-B-C(=S)-RK、-B-O-C(=S)-RK、-B-S-C(=S)-RK、-B-N(RJ)-C(=S)-RK,C1-C8链烯基、C1-C8炔基、未被取代或可以带有1-4个取代基R1e的C3-C8环烷基,
未被取代或可以带有1-4个取代基R1f的萘基,
未被取代或可以带有1-4个取代基R1g的饱和或部分不饱和杂环,
未被取代或可以带有1-4个取代基R1h的杂芳基,以及
带有选自如下的基团的C1-C6烷基:-NR1iR1j、C1-C4烷氧羰基、C3-C8环烷基、芳基、芳氧基、芳硫基、杂环基、杂环氧基和杂环硫基,其中后提到的八个基团的烷基、环烷基、芳基或杂环基结构部分可以带有1、2、3或4个选自CN、NO2、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基和C3-C8环烷基的基团,其中
B为线性或支化C1-C4亚烷基,其未被取代或可以带有1、2、3或4个选自卤素和C1-C3烷氧基的基团,
RA选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RB1、RB2独立地选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RB2′选自未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RC选自可以带有1、2、3或4个选自如下的基团的C1-C6烷基:C(=O)OH、芳氧基、杂芳氧基、芳硫基、杂芳硫基或C1-C4烷氧羰基,其中后提到的五个基团未被取代或可以带有1、2、3或4个独立地选自CN、NO2、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基和C3-C8环烷基的基团,
RC′选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RD、RE选自C2-C6链烯基,C2-C6炔基,其中后提到的两个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RD′、RE′、RF、G、RH1、RH2具有对RD、RE所给的含义之一或选自氢或C1-C6烷基,后者未被取代或带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,
RI、RK选自C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RJ选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
R1a、R1b、R1c和R1d选自氢、C1-C3烷基、C1-C3烷氧基、C3-C8环烷基、C2-C3链烯基和C2-C3链烯氧基,
R1e、R1g相互独立地选自C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基,
R1f、R1h相互独立地选自CN、NO2、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基和C3-C8环烷基,
R1i选自氢、C1-C3烷基、C1-C3烷氧基、C3-C8环烷基、C2-C3链烯基和C2-C3链烯氧基,和
R1j选自C1-C3烷基、C1-C3烷氧基、C3-C8环烷基、C2-C3链烯基和C2-C3链烯氧基,和
R2、R3、R4、R5、R6和R7各自独立地为氢、卤素、OH、SH、NH2、SO3H、COOH、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C8烷硫基、C2-C6链烯基、C2-C6链烯氧基、C2-C6链烯基氨基、C2-C6链烯硫基、C2-C6炔基、C2-C6炔氧基、C2-C6炔基氨基、C2-C6炔硫基、C1-C6烷基磺酰基、C1-C6烷基次磺酰基(alkyl-sulfoxyl)、C2-C6链烯基磺酰基、C2-C6炔基磺酰基、甲酰基、C1-C6烷基羰基、C2-C6链烯基羰基、C2-C6炔基羰基、C1-C6烷氧羰基、C2-C6链烯氧羰基、C2-C6炔氧羰基、羰氧基、C1-C6烷基羰氧基、C1-C6链烯基羰氧基、C1-C6炔基羰氧基,其中上述基团的脂族基团中的碳原子可以带有1、2或3个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合,
C(O)NRLRM、(SO2)NRLRM,其中RL和RM各自独立地为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基,其中这些基团中的碳原子可以带有1、2或3个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合,
基团Y-Ar或基团Y-Cy,其中
Y为单键、氧、硫、C1-C6链烷二基或C1-C6链烷二基氧基,
Ar为苯基、萘基或含有1、2、3或4个选自氧、硫和氮的杂原子作为环成员的单环或双环5-10员杂芳族环,其中Ar未被取代或可以带有1、2、3、4或5个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合;和
Cy为C3-C12环烷基,其未被取代或被1、2、3、4或5个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合取代;
并且其中与苯基环的相邻碳原子键合的两个基团R2、R3、R4、R5或R6可以与所述碳原子一起形成稠合苯环、稠合饱和或部分不饱和5、6或7员碳环或稠合5、6或7员杂环,该杂环含有1、2、3或4个选自O、S和N的杂原子作为环成员,并且其中该稠合环未被取代或可以带有1、2、3或4个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合。
本发明的另一目的是如上所定义的式I化合物或其盐在防治动物害虫中的用途。
本发明的另一目的是一种含有至少一种如上所定义的式I化合物和/或其可农用盐和至少一种液体或固体载体的农用组合物。
本发明的又一目的是一种含有至少一种如上所定义的式I化合物和/或其可兽用盐和至少一种可兽用液体或固体载体的兽用组合物。
本发明还提供了一种防治动物害虫的方法,该方法包括用杀虫有效量的如上所定义的式I化合物或其盐或组合物处理害虫、其食物供应源、其栖息地或其繁殖地或其中害虫生长或可能生长的植物、植物繁殖材料、土壤、区域、材料或环境或者要防止害虫侵袭或侵染的材料、植物、植物繁殖材料、土壤、表面或空间。
本发明进一步涉及一种处理或保护动物以防寄生虫侵袭或侵染的方法,包括使动物与杀寄生虫有效量的如上所定义的式I化合物或其可兽用盐接触。使动物与本发明化合物I、其盐或兽用组合物接触意味着对动物给药或用药。
本发明的再一目的是植物繁殖材料,尤其是种子,包含至少一种式I化合物和/或其可农用盐。
在式I化合物中,带有基团A的碳原子产生手性中心。因此,式I化合物可以不同对映体形式存在,或者若在基团R2-R7的任一个中存在另一手性中心,则它可以非对映体形式存在。当A为式A.2的基团时,化合物I还可以相对于N=C轴以顺式-或反式-异构体存在。本发明涉及式I化合物的每一种可能立体异构体,即单一对映体或非对映体,以及其混合物。
本发明化合物可以是无定形的或者可以一种或多种不同晶体状态(多晶形)存在,不同的晶体状态可能具有不同的宏观性能如稳定性或显示出不同的生物学性能如活性。本发明包括无定形和结晶的式I化合物,各化合物I的不同结晶状态的混合物,以及它们的无定形或结晶盐。
式I化合物的盐优选为可农用盐和可兽用盐。它们可以常规方法形成,例如若式I化合物具有碱性官能团,则通过使该化合物与所述阴离子的酸反应,或使式I的酸性化合物与合适的碱反应。
合适的可农用盐尤其是其阳离子和阴离子分别对本发明化合物的作用没有任何不利影响的那些阳离子的盐或那些酸的酸加成盐。合适的阳离子尤其是碱金属离子,优选锂、钠和钾离子;碱土金属离子,优选钙、镁和钡离子;过渡金属离子,优选锰、铜、锌和铁离子;还有铵离子(NH4 +)和其中1-4个氢原子被C1-C4烷基、C1-C4羟基烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基或苄基替代的取代铵离子。取代铵离子的实例包括甲基铵、异丙基铵、二甲基铵、二异丙基铵、三甲基铵、四甲基铵、四乙基铵、四丁基铵、2-羟基乙基铵、2-(2-羟基乙氧基)乙基铵、二(2-羟基乙基)铵、苄基三甲基铵和苄基三乙基铵,此外还有鏻离子,锍离子,优选三(C1-C4烷基)锍和氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根和C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。它们可以通过使式I化合物与对应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
术语“可兽用盐”是指在兽用盐形成领域已知且被接受的那些阳离子或阴离子的盐。例如通过含碱性氮原子如氨基的式I化合物形成的合适酸加成盐包括与无机酸的盐如盐酸盐、硫酸盐、磷酸盐和硝酸盐,以及有机酸如乙酸、马来酸、二马来酸、富马酸、二富马酸、甲烷次磺酸、甲烷磺酸和琥珀酸的盐。
术语“植物繁殖材料”包括任何可繁殖的植物部分。植物繁殖材料通常为受精和一定生长之后在母本植物中出现的裸子植物和被子植物的成熟胚珠的产品且包括种子、果实、假果、果序列以及地下茎(根状茎)、球茎、块茎、球根和接穗。术语“植物繁殖材料”尤其应理解为种子。
在各变量的上述定义中提到的有机结构部分象术语卤素一样为各基团成员的各次列举的集合性术语。前缀Cn-Cm在每种情况下表示该基团中可能的碳原子数。
术语“卤素”在每种情况下表示氟、溴、氯或碘,尤其是氟、氯或溴。
其他含义的实例为:
本文所用以及在C1-C6烷氧基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷基次磺酰基、C1-C6烷基羰基、C1-C6烷氧羰基、C1-C6烷硫基和C1-C6烷基羰氧基的烷基结构部分中的术语“C1-C6烷基”指具有1-6个碳原子的饱和直链或支化烃基,尤其是具有1-3个碳原子的基团(=C1-C3烷基)。C1-C3烷基的实例是甲基、乙基、丙基和1-甲基乙基(异丙基)。C1-C6烷基的实例进一步包括丁基、1-甲基丙基(仲丁基、2-丁基)、2-甲基丙基(异丁基)、1,1-二甲基乙基(叔丁基)、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。
本文所用术语“C1-C6卤代烷基”指具有1-6个碳原子的直链或支化饱和烷基(如上所述),其中这些基团中的部分或所有氢原子可以被如上所述的卤原子替代,例如C1-C3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。
本文所用以及在术语C1-C6烷氧羰基中的术语“C1-C6烷氧基”指经由氧原子连接的具有1-6个碳原子,优选1-3个碳原子(C1-C3烷氧基)的直链或支化饱和烷基(如上所述)。C1-C3烷氧基的实例包括甲氧基、乙氧基、OCH2-C2H5(丙氧基)和OCH(CH3)2(异丙氧基)。C1-C6烷氧基的实例进一步包括正丁氧基、OCH(CH3)C2H5(仲丁氧基)、OCH2CH(CH3)2(异丁氧基)、OC(CH3)3(叔丁氧基)、正戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、2,2-二甲基丙氧基、1-乙基丙氧基、正己氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基、1-乙基-2-甲基丙氧基等。
本文所用术语“C1-C6卤代烷氧基”指如上所述的C1-C6烷氧基,其中氢原子部分或完全被氟、氯、溴和/或碘替代。优选C1-C3卤代烷氧基,即如上所述的C1-C3烷氧基,其中氢原子部分或完全被氟、氯、溴和/或碘替代,例如氯甲氧基、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、2-氟乙氧基、2-氯乙氧基、2-溴乙氧基、2-碘乙氧基、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、五氟乙氧基、2-氟丙氧基、3-氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、2-氯丙氧基、3-氯丙氧基、2,3-二氯丙氧基、2-溴丙氧基、3-溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氯丙氧基、2,2,3,3,3-五氟丙氧基、七氟丙氧基、1-(氟甲基)-2-氟乙氧基、1-(氯甲基)-2-氯乙氧基和1-(溴甲基)-2-溴乙氧基。C1-C6卤代烷氧基的实例进一步包括4-氟丁氧基、4-氯丁氧基、4-溴丁氧基、九氟丁氧基、5-氟-1-戊氧基、5-氯-1-戊氧基、5-溴-1-戊氧基、5-碘-1-戊氧基、5,5,5-三氯-1-戊氧基、十一氟戊氧基、6-氟-1-己氧基、6-氯-1-己氧基、6-溴-1-己氧基、6-碘-1-己氧基、6,6,6-三氯-1-己氧基和十二氟己氧基。特别优选氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、2-氟乙氧基、2-氯乙氧基和2,2,2-三氟乙氧基。
本文所用术语“C1-C6烷基羰基”指经由羰基的碳原子在烷基中以任意键键合的具有1-6个碳原子,优选1-4个碳原子(=C1-C4烷基羰基)的直链或支化饱和烷基(如上所述)。C1-C4烷基羰基的实例包括C(O)CH3、C(O)C2H5、正丙基羰基、1-甲基乙基羰基、正丁基羰基、1-甲基丙基羰基、2-甲基丙基羰基和1,1-二甲基乙基羰基。C1-C6烷基羰基的实例进一步包括正戊基羰基、1-甲基丁基羰基、2-甲基丁基羰基、3-甲基丁基羰基、1,1-二甲基丙基羰基、1,2-二甲基丙基羰基、2,2-二甲基丙基羰基、1-乙基丙基羰基、正己基羰基、1-甲基戊基羰基、2-甲基戊基羰基、3-甲基戊基羰基、4-甲基戊基羰基、1,1-二甲基丁基羰基、1,2-二甲基丁基羰基、1,3-二甲基丁基羰基、2,2-二甲基丁基羰基、2,3-二甲基丁基羰基、3,3-二甲基丁基羰基、1-乙基丁基羰基、2-乙基丁基羰基、1,1,2-三甲基丙基羰基、1,2,2-三甲基丙基羰基、1-乙基-1-甲基丙基羰基或1-乙基-2-甲基丙基羰基等。
本文所用术语“C1-C6烷氧羰基”指经由羰基的碳原子连接的具有1-6个碳原子,优选1-4个碳原子(=C1-C4烷氧羰基)的直链或支化烷氧基(如上所述)(R-O-C(O)-;R=烷基)。C1-C4烷氧羰基的实例包括C(O)OCH3、C(O)OC2H5、C(O)O-CH2-C2H5、C(O)OCH(CH3)2、正丁氧羰基、C(O)OCH(CH3)-C2H5、C(O)OCH2CH(CH3)2和C(O)OC(CH3)3。C1-C6烷氧羰基的实例进一步包括正戊氧羰基、1-甲基丁氧羰基、2-甲基丁氧羰基、3-甲基丁氧羰基、2,2-二甲基丙氧羰基、1-乙基丙氧羰基、正己氧羰基、1,1-二甲基丙氧羰基、1,2-二甲基丙氧羰基、1-甲基戊氧羰基、2-甲基戊氧羰基、3-甲基戊氧羰基、4-甲基戊氧羰基、1,1-二甲基丁氧羰基、1,2-二甲基丁氧羰基、1,3-二甲基丁氧羰基、2,2-二甲基丁氧羰基、2,3-二甲基丁氧羰基、3,3-二甲基丁氧羰基、1-乙基丁氧羰基、2-乙基丁氧羰基、1,1,2-三甲基丙氧羰基、1,2,2-三甲基丙氧羰基、1-乙基-1-甲基丙氧羰基或1-乙基-2-甲基丙氧羰基。
本文所用术语“C1-C6烷基羰氧基”指经由羰氧基的碳原子在烷基中以任意键键合的具有1-6个碳原子,优选1-4个碳原子(=C1-C4烷基羰氧基)的直链或支化饱和烷基(如上所述)。C1-C4烷基羰氧基的实例包括O-CO-CH3、O-CO-C2H5、正丙基羰氧基、1-甲基乙基羰氧基、正丁基羰氧基、1-甲基丙基羰氧基、2-甲基丙基羰氧基和1,1-二甲基乙基羰氧基。C1-C6烷基羰氧基的实例进一步包括正戊基羰氧基、1-甲基丁基羰氧基、2-甲基丁基羰氧基、3-甲基丁基羰氧基、1,1-二甲基丙基羰氧基或1,2-二甲基丙基羰氧基。
本文所用术语“C1-C6烷硫基”(C1-C6烷基硫基:C1-C6烷基-S-)指经由硫原子连接的具有1-6个碳原子,优选1-3个碳原子(=C1-C3烷硫基)的直链或支化饱和烷基(如上所述)。C1-C3烷硫基的实例包括甲硫基、乙硫基、丙硫基和1-甲基乙硫基。C1-C6烷硫基的实例进一步包括丁硫基、1-甲基丙硫基、2-甲基丙硫基和1,1-二甲基乙硫基、正戊硫基、1-甲基丁硫基、2-甲基丁硫基、3-甲基丁硫基、2,2-二甲基丙硫基、1-乙基丙硫基、正己硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、1-甲基戊硫基、2-甲基戊硫基、3-甲基戊硫基、4-甲基戊硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,2-二甲基丁硫基、2,3-二甲基丁硫基、3,3-二甲基丁硫基、1-乙基丁硫基、2-乙基丁硫基、1,1,2-三甲基丙硫基、1,2,2-三甲基丙硫基、1-乙基-1-甲基丙硫基和1-乙基-2-甲基丙硫基。
本文所用术语“C1-C6卤代烷硫基”指如上所述的C1-C6烷硫基,其中氢原子部分或完全被氟、氯、溴和/或碘取代。优选C1-C3卤代烷硫基,即其中氢原子部分或完全被氟、氯、溴和/或碘取代的上述C1-C3烷硫基,例如氯甲硫基、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、2-氟乙硫基、2-氯乙硫基、2-溴乙硫基、2-碘乙硫基、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、五氟乙硫基、2-氟丙硫基、3-氟丙硫基、2,2-二氟丙硫基、2,3-二氟丙硫基、2-氯丙硫基、3-氯丙硫基、2,3-二氯丙硫基、2-溴丙硫基、3-溴丙硫基、3,3,3-三氟丙硫基、3,3,3-三氯丙硫基、2,2,3,3,3-五氟丙硫基、七氟丙硫基、1-(氟甲基)-2-氟乙硫基、1-(氯甲基)-2-氯乙硫基或1-(溴甲基)-2-溴乙硫基。C1-C6卤代烷硫基的实例进一步包括4-氟丁硫基、4-氯丁硫基、4-溴丁硫基、九氟丁硫基、5-氟-1-戊硫基、5-氯-1-戊硫基、5-溴-1-戊硫基、5-碘-1-戊硫基、5,5,5-三氯-1-戊硫基、十一氟戊硫基、6-氟-1-己硫基、6-氯-1-己硫基、6-溴-1-己硫基、6-碘-1-己硫基、6,6,6-三氯-1-己硫基和十二氟己硫基。特别优选氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、2-氟乙硫基、2-氯乙硫基和2,2,2-三氟乙硫基。
本文所用术语“C1-C6烷基次磺酰基”(C1-C6烷基亚磺酰基:C1-C6烷基-S(=O)-)指通过次磺酰基的硫原子在烷基中以任意位置键合的具有1-6个碳原子,优选1-4个碳原子(=C1-C4烷基次磺酰基)的直链或支化饱和烷基(如上所述)。C1-C4烷基亚磺酰基的实例包括S(O)CH3、S(O)C2H5、正丙基亚磺酰基、1-甲基乙基亚磺酰基、正丁基亚磺酰基、1-甲基丙基亚磺酰基、2-甲基丙基亚磺酰基和1,1-二甲基乙基亚磺酰基。C1-C6烷基亚磺酰基的实例进一步包括正戊基亚磺酰基、1-甲基丁基亚磺酰基、2-甲基丁基亚磺酰基、3-甲基丁基亚磺酰基、1,1-二甲基丙基亚磺酰基、1,2-二甲基丙基亚磺酰基、2,2-二甲基丙基亚磺酰基、1-乙基丙基亚磺酰基、正己基亚磺酰基、1-甲基戊基亚磺酰基、2-甲基戊基亚磺酰基、3-甲基戊基亚磺酰基、4-甲基戊基亚磺酰基、1,1-二甲基丁基亚磺酰基、1,2-二甲基丁基亚磺酰基、1,3-二甲基丁基亚磺酰基、2,2-二甲基丁基亚磺酰基、2,3-二甲基丁基亚磺酰基、3,3-二甲基丁基亚磺酰基、1-乙基丁基亚磺酰基、2-乙基丁基亚磺酰基、1,1,2-三甲基丙基亚磺酰基、1,2,2-三甲基丙基亚磺酰基、1-乙基-1-甲基丙基亚磺酰基和1-乙基-2-甲基丙基亚磺酰基。
本文所用术语“C1-C6烷基磺酰基”(C1-C6烷基-S(=O)2-)指通过磺酰基的硫原子在烷基中以任意位置键合的具有1-6个碳原子,优选1-4个碳原子(=C1-C4烷基磺酰基)的直链或支化饱和烷基(如上所述)。C1-C4烷基磺酰基的实例包括SO2-CH3、SO2-C2H5、正丙基磺酰基、SO2-CH(CH3)2、正丁基磺酰基、1-甲基丙基磺酰基、2-甲基丙基磺酰基和SO2-C(CH3)3。C1-C6烷基磺酰基的实例进一步包括正戊基磺酰基、1-甲基丁基磺酰基、2-甲基丁基磺酰基、3-甲基丁基磺酰基、1,1-二甲基丙基磺酰基、1,2-二甲基丙基磺酰基、2,2-二甲基丙基磺酰基、1-乙基丙基磺酰基、正己基磺酰基、1-甲基戊基磺酰基、2-甲基戊基磺酰基、3-甲基戊基磺酰基、4-甲基戊基磺酰基、1,1-二甲基丁基磺酰基、1,2-二甲基丁基磺酰基、1,3-二甲基丁基磺酰基、2,2-二甲基丁基磺酰基、2,3-二甲基丁基磺酰基、3,3-二甲基丁基磺酰基、1-乙基丁基磺酰基、2-乙基丁基磺酰基、1,1,2-三甲基丙基磺酰基、1,2,2-三甲基丙基磺酰基、1-乙基-1-甲基丙基磺酰基和1-乙基-2-甲基丙基磺酰基。
术语“C1-C6烷基氨基”指带有一个如上所定义的烷基的仲氨基,例如甲基氨基、乙基氨基、丙基氨基、1-甲基乙基氨基、丁基氨基、1-甲基丙基氨基、2-甲基丙基氨基、1,1-二甲基乙基氨基、戊基氨基、1-甲基丁基氨基、2-甲基丁基氨基、3-甲基丁基氨基、2,2-二甲基丙基氨基、1-乙基丙基氨基、己基氨基、1,1-二甲基丙基氨基、1,2-二甲基丙基氨基、1-甲基戊基氨基、2-甲基戊基氨基、3-甲基戊基氨基、4-甲基戊基氨基、1,1-二甲基丁基氨基、1,2-二甲基丁基氨基、1,3-二甲基丁基氨基、2,2-二甲基丁基氨基、2,3-二甲基丁基氨基、3,3-二甲基丁基氨基、1-乙基丁基氨基、2-乙基丁基氨基、1,1,2-三甲基丙基氨基、1,2,2-三甲基丙基氨基、1-乙基-1-甲基丙基氨基或1-乙基-2-甲基丙基氨基。
术语“二-C1-C6烷基氨基”指带有两个如上所定义的烷基的叔氨基,例如二甲基氨基、二乙基氨基、二正丙基氨基、二异丙基氨基、N-乙基-N-甲基氨基、N-(正丙基)-N-甲基氨基、N-(异丙基)-N-甲基氨基、N-(正丁基)-N-甲基氨基、N-(正戊基)-N-甲基氨基、N-(2-丁基)-N-甲基氨基、N-(异丁基)-N-甲基氨基、N-(正戊基)-N-甲基氨基、N-(正丙基)-N-乙基氨基、N-(异丙基)-N-乙基氨基、N-(正丁基)-N-乙基氨基、N-(正戊基)-N-乙基氨基、N-(2-丁基)-N-乙基氨基、N-(异丁基)-N-乙基氨基等。
本文所用以及在C2-C6链烯氧基、C2-C6链烯基氨基、C2-C6链烯硫基、C2-C6链烯基磺酰基、C2-C6链烯基羰基、C2-C6链烯氧羰基和C2-C6链烯基羰氧基的链烯基结构部分中的“C2-C6链烯基”指具有2-6个碳原子和在任意位置的双键的直链或支化不饱和烃基,例如乙烯基、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。
本文所用术语“C2-C6链烯氧基”指经由氧原子连接的具有2-6个碳原子的直链或支化链烯基(如上所述),例如乙烯氧基、烯丙氧基(丙烯-3-基氧基)、甲代烯丙氧基、丁烯-4-基氧基等。
本文所用术语“C2-C6链烯硫基”指经由硫原子连接的具有2-6个碳原子的直链或支化链烯基(如上所述),例如乙烯硫基、烯丙硫基(丙烯-3-基硫基)、甲代烯丙硫基、丁烯-4-基硫基等。
本文所用术语“C2-C6链烯基羰基”指经由羰基的碳原子在链烯基中以任意键键合的具有2-6个碳原子的直链或支化链烯基(如上所述),例如乙烯基羰基、烯丙基羰基(丙烯-3-基羰基)、甲代烯丙基羰基、丁烯-4-基羰基等。
本文所用术语“C2-C6链烯氧羰基”指经由氧羰基的碳原子键合的具有2-6个碳原子的直链或支化链烯基(如上所述)(RO-C(O)-;R=C2-C6链烯基),例如乙烯氧羰基、烯丙氧羰基(丙烯-3-基氧羰基)、甲代烯丙氧羰基、丁烯-4-基氧羰基等。
本文所用术语“C2-C6链烯基羰氧基”指经由羰氧基的氧原子键合的具有2-6个碳原子的直链或支化链烯基(如上所述)(R-C(O)-O-;R=C2-C6链烯基),例如乙烯基羰氧基、烯丙基羰氧基(丙烯-3-基羰氧基)、甲代烯丙基羰氧基、丁烯-4-基羰氧基等。
本文所用术语“C2-C6链烯基氨基”指经由硫原子连接的具有2-6个碳原子的直链或支化链烯基(如上所述),例如乙烯基氨基、烯丙基氨基(丙烯-3-基氨基)、甲代烯丙基氨基、丁烯-4-基氨基等。
本文所用术语“C2-C6链烯基磺酰基”指经由磺酰基(SO2)连接的具有2-6个碳原子的直链或支化链烯基(如上所述),例如乙烯基磺酰基、烯丙基磺酰基(丙烯-3-基磺酰基)、甲代烯丙基磺酰基、丁烯-4-基磺酰基等。
本文所用以及在C2-C6炔氧基、C2-C6炔基氨基、C2-C6炔硫基、C2-C6炔基磺酰基、C2-C6炔基羰基、C2-C6炔氧羰基和C2-C6炔基羰氧基的炔基结构部分中的术语“C2-C6炔基”指具有2-6个碳原子且含有至少一个叁键的直链或支化不饱和烃基,例如乙炔基、丙-1-炔-1-基、丙-2-炔-1-基、正丁-1-炔-1-基、正丁-1-炔-3-基、正丁-1-炔-4-基、正丁-2-炔-1-基、正戊-1-炔-1-基、正戊-1-炔-3-基、正戊-1-炔-4-基、正戊-1-炔-5-基、正戊-2-炔-1-基、正戊-2-炔-4-基、正戊-2-炔-5-基、3-甲基丁-1-炔-3-基、3-甲基丁-1-炔-4-基、正己-1-炔-1-基、正己-1-炔-3-基、正己-1-炔-4-基、正己-1-炔-5-基、正己-1-炔-6-基、正己-2-炔-1-基、正己-2-炔-4-基、正己-2-炔-5-基、正己-2-炔-6-基、正己-3-炔-1-基、正己-3-炔-2-基、3-甲基戊-1-炔-1-基、3-甲基戊-1-炔-3-基、3-甲基戊-1-炔-4-基、3-甲基戊-1-炔-5-基、4-甲基戊-1-炔-1-基、4-甲基戊-2-炔-4-基或4-甲基戊-2-炔-5-基等。
本文所用术语“C2-C6炔氧基”指经由氧原子连接的具有2-6个碳原子的直链或支化炔基(如上所述),例如炔丙氧基(丙炔-3-基氧基)、丁炔-3-基氧基、丁炔-4-基氧基等。
本文所用术语“C2-C6炔硫基”指经由硫原子连接的具有2-6个碳原子的直链或支化炔基(如上所述),例如炔丙硫基(丙炔-3-基硫基)、丁炔-3-基硫基、丁炔-4-基硫基等。
本文所用术语“C2-C6炔基羰基”指经由羰基的碳原子在炔基中以任意键键合的具有2-6个碳原子的直链或支化炔基(如上所述),例如炔丙基羰基(丙炔-3-基羰基)、丁炔-3-基羰基、丁炔-4-基羰基等。
本文所用术语“C2-C6炔氧羰基”指经由氧羰基的碳原子键合的具有2-6个碳原子的直链或支化炔基(如上所述)(RO-C(O)-;R=C2-C6炔基),例如炔丙基氧羰基(丙炔-3-基氧羰基)、丁炔-3-基氧羰基、丁炔-4-基氧羰基等。
本文所用术语“C2-C6炔基羰氧基”指经由羰氧基的氧原子键合的具有2-6个碳原子的直链或支化炔基(如上所述)(R-C(O)-O-;R=C2-C6炔基),例如炔丙基羰氧基(丙炔-3-基羰氧基)、丁炔-3-基羰氧基、丁炔-4-基羰氧基等。
本文所用术语“C2-C6炔基氨基”指经由硫原子连接的具有2-6个碳原子的直链或支化炔基(如上所述),例如炔丙基氨基(丙炔-3-基要基)、丁炔-3-基氨基、丁炔-4-基氨基等。
本文所用术语“C2-C6炔基磺酰基”指经由磺酰基(SO2)连接的具有2-6个碳原子的直链或支化炔基(如上所述),例如炔丙基磺酰基(丙炔-3-基磺酰基)、丁炔-3-基磺酰基、丁炔-4-基磺酰基等。
本文所用术语“C3-C12环烷基”指具有3-12个碳原子(=C3-C12环烷基),常常3-8个碳原子(=C3-C8环烷基),尤其是3-6个碳原子(=C3-C6环烷基)的单环或双环或多环烃基。单环基团的实例包括环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基和环癸基。双环基团的实例包括双环[2.2.1]庚基、双环[3.1.1]庚基、双环[2.2.2]辛基和双环[3.2.1]辛基。
本文所用术语“芳基”指C6-C14碳芳族基团,例如苯基、萘基、蒽基和菲基。优选芳基为苯基。
本文所用术语“芳氧基”指如上所定义的芳基,其经由氧原子与该分子的剩余部分键合。实例是苯氧基和萘氧基。
本文所用术语“芳硫基”指如上所定义的芳基,其经由硫原子与该分子的剩余部分键合。实例是苯氧基和萘氧基。
与苯基稠合的苯基是萘基。
与5或6员非芳族(即饱和或部分不饱和)杂环稠合的苯基例如为2,3-二氢苯并呋喃基、苯并氧杂环戊基(benzoxolanyl)、2,3-二氢苯并噻吩基、二氢吲哚基、苯并二氢吡喃基、苯并吡喃基、苯并二噁烷基等。下面给出与5或6员芳族杂环稠合(=与5或6员杂芳族环稠合)的苯基的实例。
本文所用术语“杂芳基”(“单环或双环5-10员杂芳族环”)指具有5或6个环成员的单环杂芳族基团,其可以与5、6或7员碳环或杂环稠合,因而具有的总环成员数为8-10,其中在每种情况下这些环成员中的1、2、3或4个,优选1、2或3个为相互独立地选自氧、氮和硫的杂原子。该杂芳基可以经由碳环成员或氮环成员与该分子的剩余部分连接。稠合的碳环或杂环选自C5-C7环烷基、5-7员杂环基和苯基。
单环5-6员杂芳族环的实例包括三嗪基、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、噁唑基、噻二唑基、噁二唑基、异噻唑基和异噁唑基。
与苯基环稠合(或对于与5-6员杂芳族环稠合的苯基环)的5-6员杂芳族环的实例是喹啉基、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[b]噻唑基、苯并噁唑基、苯并噻唑基和苯并咪唑基。与环烯基环稠合的5-6员杂芳族环的实例是二氢吲哚基、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。
术语“杂芳氧基”指经由氧原子与该分子的剩余部分键合的如上所定义的杂芳基。
术语“杂芳硫基”指经由硫原子与该分子的剩余部分键合的如上所定义的杂芳基。
术语“杂环基”(“饱和或部分不饱和杂环”)包括具有5或6个环成员和1、2、3或4个,优选1、2或3个杂原子作为环成员的非芳族饱和或部分不饱和杂环。杂环基可以经由碳环成员或氮环成员与该分子的剩余部分连接。非芳族环的实例包括吡咯烷基、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、1,3-二氧戊环基、二氧杂环戊烯基(dioxolenyl)、硫杂戊环基(thiolanyl)、二氢噻吩基、噁唑烷基、异噁唑烷基、噁唑啉基、异噁唑啉基、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、1,3-和1,4-二噁烷基、噻喃基、二氢噻喃基、四氢噻喃基、吗啉基、噻嗪基等。还包含1或2个羰基作为环成员的杂环实例包括吡咯烷-2-酮基、吡咯烷-2,5-二酮基、咪唑烷-2-酮基、噁唑烷-2-酮基、噻唑烷-2-酮基等。
术语“杂环氧基”指经由氧原子与该分子的剩余部分键合的如上所定义的杂环基。
术语“杂环硫基”指经由硫原子与该分子的剩余部分键合的如上所定义的杂环基。
本文所用术语“线性或支化C1-C6链烷二基”指具有1-6个碳原子的直链或支化饱和烷基(如上所述),其中这些基团中的氢原子之一被另一键合位置替代。线性C1-C6链烷二基的实例包括亚甲基、1,2-亚乙基、1,3-亚丙基、1,4-亚丁基、1,5-亚戊基、1,6-亚己基。支化C1-C6链烷二基的实例包括1,1-亚乙基、1,1-亚丙基、1,1-亚丁基、1-甲基-1,2-亚乙基、1,2-二甲基-1,2-亚乙基、1-乙基-1,2-亚乙基、1-甲基-1,3-亚丙基、2-甲基-1,3-亚丙基等。
式I化合物包括其中A为式A.1的基团的化合物-称为式I.1化合物,和其中A为式A.2的基团的化合物-称为式I.2化合物。
本发明的优选实施方案涉及本文所示的式I.1化合物。
下面就式I以及式I.1和I.2化合物的各变量、用途以及本发明方法和本发明组合物的特征的优选实施方案所作描述单独有效,并且优选相互组合有效。
基团X优选为硫原子。
R1优选选自-C(=O)-RC、-C(=O)-ORD、-C(=O)-SRE、-C(=O)-NRB1RB′、-C(=S)-RC′、-C(=S)-ORD′、-C(=S)-SRE′、-C(=S)-NRB1RB2、-C(=NR1e)-RC′、-C(=NR1f)-ORD′、-C(=NR1g)-SRE′、-C(=NR1h)-NRB1RB2,其中RB1、RB2、RB2′、RC、RC′、RD、RD′、Re、RE′、R1e、R1f、R1g和R1h具有前面所给含义之一。更优选R1为-C(=S)-NRB1RB2,其中RB1和RB2具有前面所给含义之一。
基团RB1和RB2优选相互独立地选自氢,C1-C3烷基,C2-C3链烯基,C2-C3炔基,其中后提到的三个基团可以带有1或2个独立地选自卤素、C1-C3烷氧基和C1-C3卤代烷氧基的取代基,未被取代或可以带有1、2或3个取代基R1e的C3-C6环烷基,未被取代或可以带有1、2或3个取代基R1f的苯基,未被取代或可以带有1、2或3个取代基Rh的吡啶基,其中R1e、R1f和R1h具有前面所给含义之一。
基团RB2′优选选自未被取代或可以带有1、2或3个取代基R1e的C3-C6环烷基,未被取代或可以带有1、2或3个取代基Rf的苯基和未被取代或可以带有1、2或3个取代基Rh的吡啶基,其中R1e、R1f和R1h具有前面所给含义之一。
基团RC优选选自带有1或2个选自C(=O)OH、芳氧基、芳硫基或C1-C4烷氧羰基的基团的C1-C3烷基,其中后提到的三个基团未被取代或可以带有1或2个独立地选自CN、NO2、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基和C3-C6环烷基的基团。
基团RC′优选选自氢,C1-C3烷基,C2-C3链烯基,C2-C3炔基,其中后提到的三个基团可以带有1或2个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C6环烷基的取代基,未被取代或可以带有1、2或3个取代基R1e的C3-C6环烷基,未被取代或可以带有1、2或3个取代基R1f的苯基和未被取代或可以带有1、2或3个取代基R1h的吡啶基,其中R1e、R1f和R1h具有前面所给含义之一。
基团RD、RE相互独立地优选选自C2-C3链烯基,C2-C3炔基,其中后提到的两个基团可以带有1、2或3个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C6环烷基的取代基,未被取代或可以带有1、2或3个取代基R1e的C3-C6环烷基,未被取代或可以带有1、2或3个取代基R1f的苯基和未被取代或可以带有1、2或3个取代基R1h的吡啶基,其中R1e、R1f和R1h具有前面所给含义之一。
基团RD′、RE′相互独立地优选具有对RD、RE所给的优选含义之一或选自氢或未被取代或带有1、2或3个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C6环烷基的取代基的C1-C3烷基。
还优选如下式I化合物,其中R1选自C1-C8链烯基、C1-C8炔基和未被取代或可以带有1-4个如前所定义的取代基R1e的C3-C8环烷基。
还优选如下式I化合物,其中R1选自-S(=O)-RF、-S(=O)2-RG、-S(=O)2-NRB1RB2′、-P(=O)RH1RH2、-P(=S)RH1RH2,其中RB1、RB2′、RF、RG、RH1和RH2具有前面所给含义之一。
基团RF、RG、RH1和RH2相互独立地优选选自氢,C1-C3烷基,C2-C3链烯基,C2-C3炔基,其中后提到的三个基团可以带有1、2或3个相互独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C6环烷基的取代基,未被取代或可以带有1、2或3个取代基R1e的C3-C6环烷基,未被取代或可以带有1、2或3个取代基R1f的苯基和未被取代或可以带有1、2或3个取代基R1h的吡啶基,其中R1e、R1f和R1h具有前面所给含义之一。
基团R2优选选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R2选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
基团R3优选选自氢、卤素、C1-C3烷基和C1-C3卤代烷基。更优选R2选自氢、氟、氯、溴、甲基、二氟甲基和三氟甲基。
还优选如下式I化合物,其中R2与R3一起形成选自-O-CH2-O-、-O-CH2-CH2-或-O-CF2-O-的二价基团。
基团R4优选选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R4选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
在本发明的一个优选实施方案中,R2和R3不为氢。
在本发明的另一优选实施方案中,R2和R4不为氢。
基团R5优选选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R5选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
基团R6优选选自卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R6选自氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
基团R7优选为氢。同样优选其中R7为卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基或C1-C3卤代烷氧基的化合物。R7尤其选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
优选在式I、I.1和I.2中的芳族结构部分:
其中基团R2、R3和R4具有前面所给含义之一且#表示式I的键合位置,选自芳族结构部分,其中R2相对于式I化合物的剩余部分的键合位置在邻位连接于碳原子上,R3连接在紧邻基团CR2的碳原子上且相对于键合位置位于间位以及R4在基团CR2的对位连接于碳原子上,如下式Ar1所示:
其中基团R2、R3和R4具有前面所给含义之一,尤其是优选含义之一且#各自表示式I的剩余部分的键合位置。
在结构部分Ar1中,基团R2优选选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R2选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
在结构部分Ar1中,基团R3优选选自氢、卤素、C1-C3烷基和C1-C3卤代烷基。更优选R2选自氢、氟、氯、溴、甲基、二氟甲基和三氟甲基。
还优选如下式I化合物,其中在结构部分Ar1中,基团R2与R3一起形成选自-O-CH2-O-、-O-CH2-CH2-或-O-CF2-O-的二价基团。
在结构部分Ar 1中,基团R4优选选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R4选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
在本发明的一个优选实施方案中,在结构部分Ar1中的基团R2和R3不为氢。
在本发明的另一优选实施方案中,在结构部分Ar 1中的基团R2和R4不为氢。
优选芳族结构部分:
其中基团R5和R6具有前面所给含义之一且#表示式I的剩余部分的键合位置,
选自芳族结构部分,其中R5相对于式I化合物的剩余部分的键合位置在间位连接于碳原子上,R6相对于键合位置在剩余的间位连接于碳原子上以及R7为氢,如下式Ar 2所示:
其中基团R5和R6具有前面所给含义之一且#表示式I的剩余部分的键合位置。
在上述结构部分Ar 2中,基团R5优选选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R5选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
在上述结构部分Ar 2中,基团R6优选选自卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。更优选R6选自氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
本发明的优选实施方案涉及式I′化合物:
其中A、R2、R3、R4、R5和R6具有前面所给含义之一。
式I′化合物包括其中A为式A.1的基团的化合物-称为式I′.1化合物,和其中A为式A.2的基团的化合物-称为式I′.2化合物。
本发明非常优选的实施方案涉及本文所示的式I′.1化合物。
在式I′.1和I′.2中,R1优选具有前面作为优选含义给出的含义之一。X尤其为硫原子。
在更优选的实施方案中,本发明涉及式I化合物,尤其是式I.1、I.2、I′、I′.1和I′.2化合物,或其对映体、非对映体或盐,其中
R2选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基,尤其是氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基;
R3选自氢、卤素、C1-C3烷基和C1-C3卤代烷基,尤其是氢、氟、氯、溴、甲基、二氟甲基和三氟甲基;或
R2与R3一起形成选自-O-CH2-CH2-、-O-CH2-O-或-O-CF2-O-的二价基团;
R4选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基,尤其是氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基;
R5选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基,尤其是氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基;和
R6选自卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基,尤其是氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
在本发明的一个优选实施方案中,在式I.1、I.2、I′、I′.1和I′.2中的基团R2和R3不为氢。
在本发明的另一优选实施方案中,在式I.1、I.2、I′、I′.1和I′.2中的基团R2和R4不为氢。
特别优选的通式I的化合物的实例为汇编在下表A-Q中的化合物。此外,对表中各变量提到的含义本身为所述取代基的特别优选实施方案,与其中提到它们的组合无关。
表A:优选的式I′.1化合物实例是式I′.1-A化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-A.1至I′.1-A.2500)。
表1
R2 | R3 | R4 | R5 | R6 | |
A-1 | F | H | H | H | F |
A-2 | Cl | H | H | H | F |
A-3 | CH3 | H | H | H | F |
A-4 | CF3 | H | H | H | F |
A-5 | OCH3 | H | H | H | F |
A-6 | F | F | H | H | F |
A-7 | Cl | F | H | H | F |
A-8 | CH3 | F | H | H | F |
A-9 | CF3 | F | H | H | F |
A-10 | OCH3 | F | H | H | F |
A-11 | F | Cl | H | H | F |
A-12 | Cl | Cl | H | H | F |
A-13 | CH3 | Cl | H | H | F |
A-14 | CF3 | Cl | H | H | F |
A-15 | OCH3 | Cl | H | H | F |
A-16 | F | CH3 | H | H | F |
A-17 | Cl | CH3 | H | H | F |
A-18 | CH3 | CH3 | H | H | F |
A-19 | CF3 | CH3 | H | H | F |
A-20 | OCH3 | CH3 | H | H | F |
A-21 | F | CF3 | H | H | F |
A-22 | Cl | CF3 | H | H | F |
A-23 | CH3 | CF3 | H | H | F |
A-24 | CF3 | CF3 | H | H | F |
A-25 | OCH3 | CF3 | H | H | F |
A-26 | F | H | F | H | F |
A-27 | Cl | H | F | H | F |
A-28 | CH3 | H | F | H | F |
A-29 | CF3 | H | F | H | F |
A-30 | OCH3 | H | F | H | F |
A-31 | F | F | F | H | F |
A-32 | Cl | F | F | H | F |
A-33 | CH3 | F | F | H | F |
A-34 | CF3 | F | F | H | F |
A-35 | OCH3 | F | F | H | F |
A-36 | F | Cl | F | H | F |
A-37 | Cl | Cl | F | H | F |
A-38 | CH3 | Cl | F | H | F |
A-39 | CF3 | Cl | F | H | F |
A-40 | OCH3 | Cl | F | H | F |
A-41 | F | CH3 | F | H | F |
A-42 | Cl | CH3 | F | H | F |
A-43 | CH3 | CH3 | F | H | F |
A-44 | CF3 | CH3 | F | H | F |
A-45 | OCH3 | CH3 | F | H | F |
A-46 | F | CF3 | F | H | F |
R2 | R3 | R4 | R5 | R6 | |
A-47 | Cl | CF3 | F | H | F |
A-48 | CH3 | CF3 | F | H | F |
A-49 | CF3 | CF3 | F | H | F |
A-50 | OCH3 | CF3 | F | H | F |
A-51 | F | H | Cl | H | F |
A-52 | Cl | H | Cl | H | F |
A-53 | CH3 | H | Cl | H | F |
A-54 | CF3 | H | Cl | H | F |
A-55 | OCH3 | H | Cl | H | F |
A-56 | F | F | Cl | H | F |
A-57 | Cl | F | Cl | H | F |
A-58 | CH3 | F | Cl | H | F |
A-59 | CF3 | F | Cl | H | F |
A-60 | OCH3 | F | Cl | H | F |
A-61 | F | Cl | Cl | H | F |
A-62 | Cl | Cl | Cl | H | F |
A-63 | CH3 | Cl | Cl | H | F |
A-64 | CF3 | Cl | Cl | H | F |
A-65 | OCH3 | Cl | Cl | H | F |
A-66 | F | CH3 | Cl | H | F |
A-67 | Cl | CH3 | Cl | H | F |
A-68 | CH3 | CH3 | Cl | H | F |
A-69 | CF3 | CH3 | Cl | H | F |
A-70 | OCH3 | CH3 | Cl | H | F |
A-71 | F | CF3 | Cl | H | F |
A-72 | Cl | CF3 | Cl | H | F |
A-73 | CH3 | CF3 | Cl | H | F |
A-74 | CF3 | CF3 | Cl | H | F |
A-75 | OCH3 | CF3 | Cl | H | F |
A-76 | F | H | CH3 | H | F |
A-77 | Cl | H | CH3 | H | F |
A-78 | CH3 | H | CH3 | H | F |
A-79 | CF3 | H | CH3 | H | F |
A-80 | OCH3 | H | CH3 | H | F |
A-81 | F | F | CH3 | H | F |
A-82 | Cl | F | CH3 | H | F |
A-83 | CH3 | F | CH3 | H | F |
A-84 | CF3 | F | CH3 | H | F |
A-85 | OCH3 | F | CH3 | H | F |
A-86 | F | Cl | CH3 | H | F |
A-87 | Cl | Cl | CH3 | H | F |
A-88 | CH3 | Cl | CH3 | H | F |
A-89 | CF3 | Cl | CH3 | H | F |
A-90 | OCH3 | Cl | CH3 | H | F |
A-91 | F | CH3 | CH3 | H | F |
A-92 | Cl | CH3 | CH3 | H | F |
A-93 | CH3 | CH3 | CH3 | H | F |
A-94 | CF3 | CH3 | CH3 | H | F |
A-95 | OCH3 | CH3 | CH3 | H | F |
A-96 | F | CF3 | CH3 | H | F |
A-97 | Cl | CF3 | CH3 | H | F |
A-98 | CH3 | CF3 | CH3 | H | F |
A-99 | CF3 | CF3 | CH3 | H | F |
A-100 | OCH3 | CF3 | CH3 | H | F |
A-101 | F | H | CF3 | H | F |
A-102 | Cl | H | CF3 | H | F |
A-103 | CH3 | H | CF3 | H | F |
A-104 | CF3 | H | CF3 | H | F |
A-105 | OCH3 | H | CF3 | H | F |
A-106 | F | F | CF3 | H | F |
A-107 | Cl | F | CF3 | H | F |
A-108 | CH3 | F | CF3 | H | F |
A-109 | CF3 | F | CF3 | H | F |
A-110 | OCH3 | F | CF3 | H | F |
A-111 | F | Cl | CF3 | H | F |
A-112 | Cl | Cl | CF3 | H | F |
A-113 | CH3 | Cl | CF3 | H | F |
A-114 | CF3 | Cl | CF3 | H | F |
A-115 | OCH3 | Cl | CF3 | H | F |
A-116 | F | CH3 | CF3 | H | F |
A-117 | Cl | CH3 | CF3 | H | F |
A-118 | CH3 | CH3 | CF3 | H | F |
A-119 | CF3 | CH3 | CF3 | H | F |
A-120 | OCH3 | CH3 | CF3 | H | F |
A-121 | F | CF3 | CF3 | H | F |
A-122 | Cl | CF3 | CF3 | H | F |
A-123 | CH3 | CF3 | CF3 | H | F |
A-124 | CF3 | CF3 | CF3 | H | F |
A-125 | OCH3 | CF3 | CF3 | H | F |
A-126 | F | H | H | F | F |
A-127 | Cl | H | H | F | F |
A-128 | CH3 | H | H | F | F |
A-129 | CF3 | H | H | F | F |
A-130 | OCH3 | H | H | F | F |
A-131 | F | F | H | F | F |
A-132 | Cl | F | H | F | F |
A-133 | CH3 | F | H | F | F |
A-134 | CF3 | F | H | F | F |
A-135 | OCH3 | F | H | F | F |
A-136 | F | Cl | H | F | F |
A-137 | Cl | Cl | H | F | F |
A-138 | CH3 | Cl | H | F | F |
A-139 | CF3 | Cl | H | F | F |
A-140 | OCH3 | Cl | H | F | F |
A-141 | F | CH3 | H | F | F |
A-142 | Cl | CH3 | H | F | F |
A-143 | CH3 | CH3 | H | F | F |
A-144 | CF3 | CH3 | H | F | F |
A-145 | OCH3 | CH3 | H | F | F |
A-146 | F | CF3 | H | F | F |
A-147 | Cl | CF3 | H | F | F |
A-148 | CH3 | CF3 | H | F | F |
A-149 | CF3 | CF3 | H | F | F |
A-150 | OCH3 | CF3 | H | F | F |
A-151 | F | H | F | F | F |
A-152 | Cl | H | F | F | F |
A-153 | CH3 | H | F | F | F |
A-154 | CF3 | H | F | F | F |
A-155 | OCH3 | H | F | F | F |
A-156 | F | F | F | F | F |
A-157 | Cl | F | F | F | F |
A-158 | CH3 | F | F | F | F |
A-159 | CF3 | F | F | F | F |
A-160 | OCH3 | F | F | F | F |
A-161 | F | Cl | F | F | F |
A-162 | Cl | Cl | F | F | F |
A-163 | CH3 | Cl | F | F | F |
A-164 | CF3 | Cl | F | F | F |
A-165 | OCH3 | Cl | F | F | F |
A-166 | F | CH3 | F | F | F |
A-167 | Cl | CH3 | F | F | F |
A-168 | CH3 | CH3 | F | F | F |
A-169 | CF3 | CH3 | F | F | F |
A-170 | OCH3 | CH3 | F | F | F |
A-171 | F | CF3 | F | F | F |
A-172 | Cl | CF3 | F | F | F |
A-173 | CH3 | CF3 | F | F | F |
A-174 | CF3 | CF3 | F | F | F |
A-175 | OCH3 | CF3 | F | F | F |
A-176 | F | H | Cl | F | F |
A-177 | Cl | H | Cl | F | F |
A-178 | CH3 | H | Cl | F | F |
A-179 | CF3 | H | Cl | F | F |
A-180 | OCH3 | H | Cl | F | F |
A-181 | F | F | Cl | F | F |
A-182 | Cl | F | Cl | F | F |
A-183 | CH3 | F | Cl | F | F |
A-184 | CF3 | F | Cl | F | F |
A-185 | OCH3 | F | Cl | F | F |
A-186 | F | Cl | Cl | F | F |
A-187 | Cl | Cl | Cl | F | F |
A-188 | CH3 | Cl | Cl | F | F |
A-189 | CF3 | Cl | Cl | F | F |
A-190 | OCH3 | Cl | Cl | F | F |
A-191 | F | CH3 | Cl | F | F |
A-192 | Cl | CH3 | Cl | F | F |
A-193 | CH3 | CH3 | Cl | F | F |
A-194 | CF3 | CH3 | Cl | F | F |
A-195 | OCH3 | CH3 | Cl | F | F |
A-196 | F | CF3 | Cl | F | F |
A-197 | Cl | CF3 | Cl | F | F |
A-198 | CH3 | CF3 | Cl | F | F |
A-199 | CF3 | CF3 | Cl | F | F |
A-200 | OCH3 | CF3 | Cl | F | F |
A-201 | F | H | CH3 | F | F |
A-202 | Cl | H | CH3 | F | F |
A-203 | CH3 | H | CH3 | F | F |
A-204 | CF3 | H | CH3 | F | F |
A-205 | OCH3 | H | CH3 | F | F |
A-206 | F | F | CH3 | F | F |
A-207 | Cl | F | CH3 | F | F |
A-208 | CH3 | F | CH3 | F | F |
A-209 | CF3 | F | CH3 | F | F |
A-210 | OCH3 | F | CH3 | F | F |
A-211 | F | Cl | CH3 | F | F |
A-212 | Cl | Cl | CH3 | F | F |
A-213 | CH3 | Cl | CH3 | F | F |
A-214 | CF3 | Cl | CH3 | F | F |
A-215 | OCH3 | Cl | CH3 | F | F |
A-216 | F | CH3 | CH3 | F | F |
A-217 | Cl | CH3 | CH3 | F | F |
A-218 | CH3 | CH3 | CH3 | F | F |
A-219 | CF3 | CH3 | CH3 | F | F |
A-220 | OCH3 | CH3 | CH3 | F | F |
A-221 | F | CF3 | CH3 | F | F |
A-222 | Cl | CF3 | CH3 | F | F |
A-223 | CH3 | CF3 | CH3 | F | F |
A-224 | CF3 | CF3 | CH3 | F | F |
A-225 | OCH3 | CF3 | CH3 | F | F |
A-226 | F | H | CF3 | F | F |
A-227 | Cl | H | CF3 | F | F |
A-228 | CH3 | H | CF3 | F | F |
A-229 | CF3 | H | CF3 | F | F |
A-230 | OCH3 | H | CF3 | F | F |
A-231 | F | F | CF3 | F | F |
A-232 | Cl | F | CF3 | F | F |
A-233 | CH3 | F | CF3 | F | F |
A-234 | CF3 | F | CF3 | F | F |
A-235 | OCH3 | F | CF3 | F | F |
A-236 | F | Cl | CF3 | F | F |
A-237 | Cl | Cl | CF3 | F | F |
A-238 | CH3 | Cl | CF3 | F | F |
A-239 | CF3 | Cl | CF3 | F | F |
A-240 | OCH3 | Cl | CF3 | F | F |
A-241 | F | CH3 | CF3 | F | F |
A-242 | Cl | CH3 | CF3 | F | F |
A-243 | CH3 | CH3 | CF3 | F | F |
A-244 | CF3 | CH3 | CF3 | F | F |
A-245 | OCH3 | CH3 | CF3 | F | F |
A-246 | F | CF3 | CF3 | F | F |
A-247 | Cl | CF3 | CF3 | F | F |
A-248 | CH3 | CF3 | CF3 | F | F |
A-249 | CF3 | CF3 | CF3 | F | F |
A-250 | OCH3 | CF3 | CF3 | F | F |
A-251 | F | H | H | Cl | F |
A-252 | Cl | H | H | Cl | F |
A-253 | CH3 | H | H | Cl | F |
A-254 | CF3 | H | H | Cl | F |
A-255 | OCH3 | H | H | Cl | F |
A-256 | F | F | H | Cl | F |
A-257 | Cl | F | H | Cl | F |
A-258 | CH3 | F | H | Cl | F |
A-259 | CF3 | F | H | Cl | F |
A-260 | OCH3 | F | H | Cl | F |
A-261 | F | Cl | H | Cl | F |
A-262 | Cl | Cl | H | Cl | F |
A-263 | CH3 | Cl | H | Cl | F |
A-264 | CF3 | Cl | H | Cl | F |
A-265 | OCH3 | Cl | H | Cl | F |
A-266 | F | CH3 | H | Cl | F |
A-267 | Cl | CH3 | H | Cl | F |
A-268 | CH3 | CH3 | H | Cl | F |
A-269 | CF3 | CH3 | H | Cl | F |
A-270 | OCH3 | CH3 | H | Cl | F |
A-271 | F | CF3 | H | Cl | F |
A-272 | Cl | CF3 | H | Cl | F |
A-273 | CH3 | CF3 | H | Cl | F |
A-274 | CF3 | CF3 | H | Cl | F |
A-275 | OCH3 | CF3 | H | Cl | F |
A-276 | F | H | F | Cl | F |
A-277 | Cl | H | F | Cl | F |
A-278 | CH3 | H | F | Cl | F |
A-279 | CF3 | H | F | Cl | F |
A-280 | OCH3 | H | F | Cl | F |
A-281 | F | F | F | Cl | F |
A-282 | Cl | F | F | Cl | F |
A-283 | CH3 | F | F | Cl | F |
A-284 | CF3 | F | F | Cl | F |
A-285 | OCH3 | F | F | Cl | F |
A-286 | F | Cl | F | Cl | F |
A-287 | Cl | Cl | F | Cl | F |
A-288 | CH3 | Cl | F | Cl | F |
A-289 | CF3 | Cl | F | Cl | F |
A-290 | OCH3 | Cl | F | Cl | F |
A-291 | F | CH3 | F | Cl | F |
A-292 | Cl | CH3 | F | Cl | F |
A-293 | CH3 | CH3 | F | Cl | F |
A-294 | CF3 | CH3 | F | Cl | F |
A-295 | OCH3 | CH3 | F | Cl | F |
A-296 | F | CF3 | F | Cl | F |
A-297 | Cl | CF3 | F | Cl | F |
A-298 | CH3 | CF3 | F | Cl | F |
A-299 | CF3 | CF3 | F | Cl | F |
A-300 | OCH3 | CF3 | F | Cl | F |
A-301 | F | H | Cl | Cl | F |
A-302 | Cl | H | Cl | Cl | F |
A-303 | CH3 | H | Cl | Cl | F |
A-304 | CF3 | H | Cl | Cl | F |
A-305 | OCH3 | H | Cl | Cl | F |
A-306 | F | F | Cl | Cl | F |
A-307 | Cl | F | Cl | Cl | F |
A-308 | CH3 | F | Cl | Cl | F |
A-309 | CF3 | F | Cl | Cl | F |
A-310 | OCH3 | F | Cl | Cl | F |
A-311 | F | Cl | Cl | Cl | F |
A-312 | Cl | Cl | Cl | Cl | F |
A-313 | CH3 | Cl | Cl | Cl | F |
A-314 | CF3 | Cl | Cl | Cl | F |
A-315 | OCH3 | Cl | Cl | Cl | F |
A-316 | F | CH3 | Cl | Cl | F |
A-317 | Cl | CH3 | Cl | Cl | F |
A-318 | CH3 | CH3 | Cl | Cl | F |
A-319 | CF3 | CH3 | Cl | Cl | F |
A-320 | OCH3 | CH3 | Cl | Cl | F |
A-321 | F | CF3 | Cl | Cl | F |
A-322 | Cl | CF3 | Cl | Cl | F |
A-323 | CH3 | CF3 | Cl | Cl | F |
A-324 | CF3 | CF3 | Cl | Cl | F |
A-325 | OCH3 | CF3 | Cl | Cl | F |
A-326 | F | H | CH3 | Cl | F |
A-327 | Cl | H | CH3 | Cl | F |
A-328 | CH3 | H | CH3 | Cl | F |
A-329 | CF3 | H | CH3 | Cl | F |
A-330 | OCH3 | H | CH3 | Cl | F |
A-331 | F | F | CH3 | Cl | F |
A-332 | Cl | F | CH3 | Cl | F |
A-333 | CH3 | F | CH3 | Cl | F |
A-334 | CF3 | F | CH3 | Cl | F |
A-335 | OCH3 | F | CH3 | Cl | F |
A-336 | F | Cl | CH3 | Cl | F |
A-337 | Cl | Cl | CH3 | Cl | F |
A-338 | CH3 | Cl | CH3 | Cl | F |
A-339 | CF3 | Cl | CH3 | Cl | F |
A-340 | OCH3 | Cl | CH3 | Cl | F |
A-341 | F | CH3 | CH3 | Cl | F |
A-342 | Cl | CH3 | CH3 | Cl | F |
A-343 | CH3 | CH3 | CH3 | Cl | F |
A-344 | CF3 | CH3 | CH3 | Cl | F |
A-345 | OCH3 | CH3 | CH3 | Cl | F |
A-346 | F | CF3 | CH3 | Cl | F |
A-347 | Cl | CF3 | CH3 | Cl | F |
A-348 | CH3 | CF3 | CH3 | Cl | F |
A-349 | CF3 | CF3 | CH3 | Cl | F |
A-350 | OCH3 | CF3 | CH3 | Cl | F |
A-351 | F | H | CF3 | Cl | F |
A-352 | Cl | H | CF3 | Cl | F |
A-353 | CH3 | H | CF3 | Cl | F |
A-354 | CF3 | H | CF3 | Cl | F |
A-355 | OCH3 | H | CF3 | Cl | F |
A-356 | F | F | CF3 | Cl | F |
A-357 | Cl | F | CF3 | Cl | F |
A-358 | CH3 | F | CF3 | Cl | F |
A-359 | CF3 | F | CF3 | Cl | F |
A-360 | OCH3 | F | CF3 | Cl | F |
A-361 | F | Cl | CF3 | Cl | F |
A-362 | Cl | Cl | CF3 | Cl | F |
A-363 | CH3 | Cl | CF3 | Cl | F |
A-364 | CF3 | Cl | CF3 | Cl | F |
A-365 | OCH3 | Cl | CF3 | Cl | F |
A-366 | F | CH3 | CF3 | Cl | F |
A-367 | Cl | CH3 | CF3 | Cl | F |
A-368 | CH3 | CH3 | CF3 | Cl | F |
A-369 | CF3 | CH3 | CF3 | Cl | F |
A-370 | OCH3 | CH3 | CF3 | Cl | F |
A-371 | F | CF3 | CF3 | Cl | F |
A-372 | Cl | CF3 | CF3 | Cl | F |
A-373 | CH3 | CF3 | CF3 | Cl | F |
A-374 | CF3 | CF3 | CF3 | Cl | F |
A-375 | OCH3 | CF3 | CF3 | Cl | F |
A-376 | F | H | H | CH3 | F |
A-377 | Cl | H | H | CH3 | F |
A-378 | CH3 | H | H | CH3 | F |
A-379 | CF3 | H | H | CH3 | F |
A-380 | OCH3 | H | H | CH3 | F |
A-381 | F | F | H | CH3 | F |
A-382 | Cl | F | H | CH3 | F |
A-383 | CH3 | F | H | CH3 | F |
A-384 | CF3 | F | H | CH3 | F |
A-385 | OCH3 | F | H | CH3 | F |
A-386 | F | Cl | H | CH3 | F |
A-387 | Cl | Cl | H | CH3 | F |
A-388 | CH3 | Cl | H | CH3 | F |
A-389 | CF3 | Cl | H | CH3 | F |
A-390 | OCH3 | Cl | H | CH3 | F |
A-391 | F | CH3 | H | CH3 | F |
A-392 | Cl | CH3 | H | CH3 | F |
A-393 | CH3 | CH3 | H | CH3 | F |
A-394 | CF3 | CH3 | H | CH3 | F |
A-395 | OCH3 | CH3 | H | CH3 | F |
A-396 | F | CF3 | H | CH3 | F |
A-397 | Cl | CF3 | H | CH3 | F |
A-398 | CH3 | CF3 | H | CH3 | F |
A-399 | CF3 | CF3 | H | CH3 | F |
A-400 | OCH3 | CF3 | H | CH3 | F |
A-401 | F | H | F | CH3 | F |
A-402 | Cl | H | F | CH3 | F |
A-403 | CH3 | H | F | CH3 | F |
A-404 | CF3 | H | F | CH3 | F |
A-405 | OCH3 | H | F | CH3 | F |
A-406 | F | F | F | CH3 | F |
A-407 | Cl | F | F | CH3 | F |
A-408 | CH3 | F | F | CH3 | F |
A-409 | CF3 | F | F | CH3 | F |
A-410 | OCH3 | F | F | CH3 | F |
A-411 | F | Cl | F | CH3 | F |
A-412 | Cl | Cl | F | CH3 | F |
A-413 | CH3 | Cl | F | CH3 | F |
A-414 | CF3 | Cl | F | CH3 | F |
A-415 | OCH3 | Cl | F | CH3 | F |
A-416 | F | CH3 | F | CH3 | F |
A-417 | Cl | CH3 | F | CH3 | F |
A-418 | CH3 | CH3 | F | CH3 | F |
A-419 | CF3 | CH3 | F | CH3 | F |
A-420 | OCH3 | CH3 | F | CH3 | F |
A-421 | F | CF3 | F | CH3 | F |
A-422 | Cl | CF3 | F | CH3 | F |
A-423 | CH3 | CF3 | F | CH3 | F |
A-424 | CF3 | CF3 | F | CH3 | F |
A-425 | OCH3 | CF3 | F | CH3 | F |
A-426 | F | H | Cl | CH3 | F |
A-427 | Cl | H | Cl | CH3 | F |
A-428 | CH3 | H | Cl | CH3 | F |
A-429 | CF3 | H | Cl | CH3 | F |
A-430 | OCH3 | H | Cl | CH3 | F |
A-431 | F | F | Cl | CH3 | F |
A-432 | Cl | F | Cl | CH3 | F |
A-433 | CH3 | F | Cl | CH3 | F |
A-434 | CF3 | F | Cl | CH3 | F |
A-435 | OCH3 | F | Cl | CH3 | F |
A-436 | F | Cl | Cl | CH3 | F |
A-437 | Cl | Cl | Cl | CH3 | F |
A-438 | CH3 | Cl | Cl | CH3 | F |
A-439 | CF3 | Cl | Cl | CH3 | F |
A-440 | OCH3 | Cl | Cl | CH3 | F |
A-441 | F | CH3 | Cl | CH3 | F |
A-442 | Cl | CH3 | Cl | CH3 | F |
A-443 | CH3 | CH3 | Cl | CH3 | F |
A-444 | CF3 | CH3 | Cl | CH3 | F |
A-445 | OCH3 | CH3 | Cl | CH3 | F |
A-446 | F | CF3 | Cl | CH3 | F |
A-447 | Cl | CF3 | Cl | CH3 | F |
A-448 | CH3 | CF3 | Cl | CH3 | F |
A-449 | CF3 | CF3 | Cl | CH3 | F |
A-450 | OCH3 | CF3 | Cl | CH3 | F |
A-451 | F | H | CH3 | CH3 | F |
A-452 | Cl | H | CH3 | CH3 | F |
A-453 | CH3 | H | CH3 | CH3 | F |
A-454 | CF3 | H | CH3 | CH3 | F |
A-455 | OCH3 | H | CH3 | CH3 | F |
A-456 | F | F | CH3 | CH3 | F |
A-457 | Cl | F | CH3 | CH3 | F |
A-458 | CH3 | F | CH3 | CH3 | F |
A-459 | CF3 | F | CH3 | CH3 | F |
A-460 | OCH3 | F | CH3 | CH3 | F |
A-461 | F | Cl | CH3 | CH3 | F |
A-462 | Cl | Cl | CH3 | CH3 | F |
A-463 | CH3 | Cl | CH3 | CH3 | F |
A-464 | CF3 | Cl | CH3 | CH3 | F |
A-465 | OCH3 | Cl | CH3 | CH3 | F |
A-466 | F | CH3 | CH3 | CH3 | F |
A-467 | Cl | CH3 | CH3 | CH3 | F |
A-468 | CH3 | CH3 | CH3 | CH3 | F |
A-469 | CF3 | CH3 | CH3 | CH3 | F |
A-470 | OCH3 | CH3 | CH3 | CH3 | F |
A-471 | F | CF3 | CH3 | CH3 | F |
A-472 | Cl | CF3 | CH3 | CH3 | F |
A-473 | CH3 | CF3 | CH3 | CH3 | F |
A-474 | CF3 | CF3 | CH3 | CH3 | F |
A-475 | OCH3 | CF3 | CH3 | CH3 | F |
A-476 | F | H | CF3 | CH3 | F |
A-477 | Cl | H | CF3 | CH3 | F |
A-478 | CH3 | H | CF3 | CH3 | F |
A-479 | CF3 | H | CF3 | CH3 | F |
A-480 | OCH3 | H | CF3 | CH3 | F |
A-481 | F | F | CF3 | CH3 | F |
A-482 | Cl | F | CF3 | CH3 | F |
A-483 | CH3 | F | CF3 | CH3 | F |
A-484 | CF3 | F | CF3 | CH3 | F |
A-485 | OCH3 | F | CF3 | CH3 | F |
A-486 | F | Cl | CF3 | CH3 | F |
A-487 | Cl | Cl | CF3 | CH3 | F |
A-488 | CH3 | Cl | CF3 | CH3 | F |
A-489 | CF3 | Cl | CF3 | CH3 | F |
A-490 | OCH3 | Cl | CF3 | CH3 | F |
A-491 | F | CH3 | CF3 | CH3 | F |
A-492 | Cl | CH3 | CF3 | CH3 | F |
A-493 | CH3 | CH3 | CF3 | CH3 | F |
A-494 | CF3 | CH3 | CF3 | CH3 | F |
A-495 | OCH3 | CH3 | CF3 | CH3 | F |
A-496 | F | CF3 | CF3 | CH3 | F |
A-497 | Cl | CF3 | CF3 | CH3 | F |
A-498 | CH3 | CF3 | CF3 | CH3 | F |
A-499 | CF3 | CF3 | CF3 | CH3 | F |
A-500 | OCH3 | CF3 | CF3 | CH3 | F |
A-501 | F | H | H | CF3 | F |
A-502 | Cl | H | H | CF3 | F |
A-503 | CH3 | H | H | CF3 | F |
A-504 | CF3 | H | H | CF3 | F |
A-505 | OCH3 | H | H | CF3 | F |
A-506 | F | F | H | CF3 | F |
A-507 | Cl | F | H | CF3 | F |
A-508 | CH3 | F | H | CF3 | F |
A-509 | CF3 | F | H | CF3 | F |
A-510 | OCH3 | F | H | CF3 | F |
A-511 | F | Cl | H | CF3 | F |
A-512 | Cl | Cl | H | CF3 | F |
A-513 | CH3 | Cl | H | CF3 | F |
A-514 | CF3 | Cl | H | CF3 | F |
A-515 | OCH3 | Cl | H | CF3 | F |
A-516 | F | CH3 | H | CF3 | F |
A-517 | Cl | CH3 | H | CF3 | F |
A-518 | CH3 | CH3 | H | CF3 | F |
A-519 | CF3 | CH3 | H | CF3 | F |
A-520 | OCH3 | CH3 | H | CF3 | F |
A-521 | F | CF3 | H | CF3 | F |
A-522 | Cl | CF3 | H | CF3 | F |
A-523 | CH3 | CF3 | H | CF3 | F |
A-524 | CF3 | CF3 | H | CF3 | F |
A-525 | OCH3 | CF3 | H | CF3 | F |
A-526 | F | H | F | CF3 | F |
A-527 | Cl | H | F | CF3 | F |
A-528 | CH3 | H | F | CF3 | F |
A-529 | CF3 | H | F | CF3 | F |
A-530 | OCH3 | H | F | CF3 | F |
A-531 | F | F | F | CF3 | F |
A-532 | Cl | F | F | CF3 | F |
A-533 | CH3 | F | F | CF3 | F |
A-534 | CF3 | F | F | CF3 | F |
A-535 | OCH3 | F | F | CF3 | F |
A-536 | F | Cl | F | CF3 | F |
A-537 | Cl | Cl | F | CF3 | F |
A-538 | CH3 | Cl | F | CF3 | F |
A-539 | CF3 | Cl | F | CF3 | F |
A-540 | OCH3 | Cl | F | CF3 | F |
A-541 | F | CH3 | F | CF3 | F |
A-542 | Cl | CH3 | F | CF3 | F |
A-543 | CH3 | CH3 | F | CF3 | F |
A-544 | CF3 | CH3 | F | CF3 | F |
A-545 | OCH3 | CH3 | F | CF3 | F |
A-546 | F | CF3 | F | CF3 | F |
A-547 | Cl | CF3 | F | CF3 | F |
A-548 | CH3 | CF3 | F | CF3 | F |
A-549 | CF3 | CF3 | F | CF3 | F |
A-550 | OCH3 | CF3 | F | CF3 | F |
A-551 | F | H | Cl | CF3 | F |
A-552 | Cl | H | Cl | CF3 | F |
A-553 | CH3 | H | Cl | CF3 | F |
A-554 | CF3 | H | Cl | CF3 | F |
A-555 | OCH3 | H | Cl | CF3 | F |
A-556 | F | F | Cl | CF3 | F |
A-557 | Cl | F | Cl | CF3 | F |
A-558 | CH3 | F | Cl | CF3 | F |
A-559 | CF3 | F | Cl | CF3 | F |
A-560 | OCH3 | F | Cl | CF3 | F |
A-561 | F | Cl | Cl | CF3 | F |
A-562 | Cl | Cl | Cl | CF3 | F |
A-563 | CH3 | Cl | Cl | CF3 | F |
A-564 | CF3 | Cl | Cl | CF3 | F |
A-565 | OCH3 | Cl | Cl | CF3 | F |
A-566 | F | CH3 | Cl | CF3 | F |
A-567 | Cl | CH3 | Cl | CF3 | F |
A-568 | CH3 | CH3 | Cl | CF3 | F |
A-569 | CF3 | CH3 | Cl | CF3 | F |
A-570 | OCH3 | CH3 | Cl | CF3 | F |
A-571 | F | CF3 | Cl | CF3 | F |
A-572 | Cl | CF3 | Cl | CF3 | F |
A-573 | CH3 | CF3 | Cl | CF3 | F |
A-574 | CF3 | CF3 | Cl | CF3 | F |
A-575 | OCH3 | CF3 | Cl | CF3 | F |
A-576 | F | H | CH3 | CF3 | F |
A-577 | Cl | H | CH3 | CF3 | F |
A-578 | CH3 | H | CH3 | CF3 | F |
A-579 | CF3 | H | CH3 | CF3 | F |
A-580 | OCH3 | H | CH3 | CF3 | F |
A-581 | F | F | CH3 | CF3 | F |
A-582 | Cl | F | CH3 | CF3 | F |
A-583 | CH3 | F | CH3 | CF3 | F |
A-584 | CF3 | F | CH3 | CF3 | F |
A-585 | OCH3 | F | CH3 | CF3 | F |
A-586 | F | Cl | CH3 | CF3 | F |
A-587 | Cl | Cl | CH3 | CF3 | F |
A-588 | CH3 | Cl | CH3 | CF3 | F |
A-589 | CF3 | Cl | CH3 | CF3 | F |
A-590 | OCH3 | Cl | CH3 | CF3 | F |
A-591 | F | CH3 | CH3 | CF3 | F |
A-592 | Cl | CH3 | CH3 | CF3 | F |
A-593 | CH3 | CH3 | CH3 | CF3 | F |
A-594 | CF3 | CH3 | CH3 | CF3 | F |
A-595 | OCH3 | CH3 | CH3 | CF3 | F |
A-596 | F | CF3 | CH3 | CF3 | F |
A-597 | Cl | CF3 | CH3 | CF3 | F |
A-598 | CH3 | CF3 | CH3 | CF3 | F |
A-599 | CF3 | CF3 | CH3 | CF3 | F |
A-600 | OCH3 | CF3 | CH3 | CF3 | F |
A-601 | F | H | CF3 | CF3 | F |
A-602 | Cl | H | CF3 | CF3 | F |
A-603 | CH3 | H | CF3 | CF3 | F |
A-604 | CF3 | H | CF3 | CF3 | F |
A-605 | OCH3 | H | CF3 | CF3 | F |
A-606 | F | F | CF3 | CF3 | F |
A-607 | Cl | F | CF3 | CF3 | F |
A-608 | CH3 | F | CF3 | CF3 | F |
A-609 | CF3 | F | CF3 | CF3 | F |
A-610 | OCH3 | F | CF3 | CF3 | F |
A-611 | F | Cl | CF3 | CF3 | F |
A-612 | Cl | C | CF3 | CF3 | F |
A-613 | CH3 | Cl | CF3 | CF3 | F |
A-614 | CF3 | Cl | CF3 | CF3 | F |
A-615 | OCH3 | Cl | CF3 | CF3 | F |
A-616 | F | CH3 | CF3 | CF3 | F |
A-617 | Cl | CH3 | CF3 | CF3 | F |
A-618 | CH3 | CH3 | CF3 | CF3 | F |
A-619 | CF3 | CH3 | CF3 | CF3 | F |
A-620 | OCH3 | CH3 | CF3 | CF3 | F |
A-621 | F | CF3 | CF3 | CF3 | F |
A-622 | Cl | CF3 | CF3 | CF3 | F |
A-623 | CH3 | CF3 | CF3 | CF3 | F |
A-624 | CF3 | CF3 | CF3 | CF3 | F |
A-625 | OCH3 | CF3 | CF3 | CF3 | F |
A-626 | F | H | H | H | Cl |
A-627 | Cl | H | H | H | Cl |
A-628 | CH3 | H | H | H | Cl |
A-629 | CF3 | H | H | H | Cl |
A-630 | OCH3 | H | H | H | Cl |
A-631 | F | F | H | H | Cl |
A-632 | Cl | F | H | H | Cl |
A-633 | CH3 | F | H | H | Cl |
A-634 | CF3 | F | H | H | Cl |
A-635 | OCH3 | F | H | H | Cl |
A-636 | F | Cl | H | H | Cl |
A-637 | Cl | Cl | H | H | Cl |
A-638 | CH3 | Cl | H | H | Cl |
A-639 | CF3 | Cl | H | H | Cl |
A-640 | OCH3 | Cl | H | H | Cl |
A-641 | F | CH3 | H | H | Cl |
A-642 | Cl | CH3 | H | H | Cl |
A-643 | CH3 | CH3 | H | H | Cl |
A-644 | CF3 | CH3 | H | H | Cl |
A-645 | OCH3 | CH3 | H | H | Cl |
A-646 | F | CF3 | H | H | Cl |
A-647 | Cl | CF3 | H | H | Cl |
A-648 | CH3 | CF3 | H | H | Cl |
A-649 | CF3 | CF3 | H | H | Cl |
A-650 | OCH3 | CF3 | H | H | Cl |
A-651 | F | H | F | H | Cl |
A-652 | Cl | H | F | H | Cl |
A-653 | CH3 | H | F | H | Cl |
A-654 | CF3 | H | F | H | Cl |
A-655 | OCH3 | H | F | H | Cl |
A-656 | F | F | F | H | Cl |
A-657 | Cl | F | F | H | Cl |
A-658 | CH3 | F | F | H | Cl |
A-659 | CF3 | F | F | H | Cl |
A-660 | OCH3 | F | F | H | Cl |
A-661 | F | Cl | F | H | Cl |
A-662 | Cl | Cl | F | H | Cl |
A-663 | CH3 | Cl | F | H | Cl |
A-664 | CF3 | Cl | F | H | Cl |
A-665 | OCH3 | Cl | F | H | Cl |
A-666 | F | CH3 | F | H | Cl |
A-667 | Cl | CH3 | F | H | Cl |
A-668 | CH3 | CH3 | F | H | Cl |
A-669 | CF3 | CH3 | F | H | Cl |
A-670 | OCH3 | CH3 | F | H | Cl |
A-671 | F | CF3 | F | H | Cl |
A-672 | Cl | CF3 | F | H | Cl |
A-673 | CH3 | CF3 | F | H | Cl |
A-674 | CF3 | CF3 | F | H | Cl |
A-675 | OCH3 | CF3 | F | H | Cl |
A-676 | F | H | Cl | H | Cl |
A-677 | Cl | H | Cl | H | Cl |
A-678 | CH3 | H | Cl | H | Cl |
A-679 | CF3 | H | Cl | H | Cl |
A-680 | OCH3 | H | Cl | H | Cl |
A-681 | F | F | Cl | H | Cl |
A-682 | Cl | F | Cl | H | Cl |
A-683 | CH3 | F | Cl | H | Cl |
A-684 | CF3 | F | Cl | H | Cl |
A-685 | OCH3 | F | Cl | H | Cl |
A-686 | F | Cl | Cl | H | Cl |
A-687 | Cl | Cl | Cl | H | Cl |
A-688 | CH3 | Cl | Cl | H | Cl |
A-689 | CF3 | Cl | Cl | H | Cl |
A-690 | OCH3 | Cl | Cl | H | Cl |
A-691 | F | CH3 | Cl | H | Cl |
A-692 | Cl | CH3 | Cl | H | Cl |
A-693 | CH3 | CH3 | Cl | H | Cl |
A-694 | CF3 | CH3 | Cl | H | Cl |
A-695 | OCH3 | CH3 | Cl | H | Cl |
A-696 | F | CF3 | Cl | H | Cl |
A-697 | Cl | CF3 | Cl | H | Cl |
A-698 | CH3 | CF3 | Cl | H | Cl |
A-699 | CF3 | CF3 | Cl | H | Cl |
A-700 | OCH3 | CF3 | Cl | H | Cl |
A-701 | F | H | CH3 | H | Cl |
A-702 | Cl | H | CH3 | H | Cl |
A-703 | CH3 | H | CH3 | H | Cl |
A-704 | CF3 | H | CH3 | H | Cl |
A-705 | OCH3 | H | CH3 | H | Cl |
A-706 | F | F | CH3 | H | Cl |
A-707 | Cl | F | CH3 | H | Cl |
A-708 | CH3 | F | CH3 | H | Cl |
A-709 | CF3 | F | CH3 | H | Cl |
A-710 | OCH3 | F | CH3 | H | Cl |
A-711 | F | Cl | CH3 | H | Cl |
A-712 | Cl | Cl | CH3 | H | Cl |
A-713 | CH3 | Cl | CH3 | H | Cl |
A-714 | CF3 | Cl | CH3 | H | Cl |
A-715 | OCH3 | Cl | CH3 | H | Cl |
A-716 | F | CH3 | CH3 | H | Cl |
A-717 | Cl | CH3 | CH3 | H | Cl |
A-718 | CH3 | CH3 | CH3 | H | Cl |
A-719 | CF3 | CH3 | CH3 | H | Cl |
A-720 | OCH3 | CH3 | CH3 | H | Cl |
A-721 | F | CF3 | CH3 | H | Cl |
A-722 | Cl | CF3 | CH3 | H | Cl |
A-723 | CH3 | CF3 | CH3 | H | Cl |
A-724 | CF3 | CF3 | CH3 | H | Cl |
A-725 | OCH3 | CF3 | CH3 | H | Cl |
A-726 | F | H | CF3 | H | Cl |
A-727 | Cl | H | CF3 | H | Cl |
A-728 | CH3 | H | CF3 | H | Cl |
A-729 | CF3 | H | CF3 | H | Cl |
A-730 | OCH3 | H | CF3 | H | Cl |
A-731 | F | F | CF3 | H | Cl |
A-732 | Cl | F | CF3 | H | Cl |
A-733 | CH3 | F | CF3 | H | Cl |
A-734 | CF3 | F | CF3 | H | Cl |
A-735 | OCH3 | F | CF3 | H | Cl |
A-736 | F | Cl | CF3 | H | Cl |
A-737 | Cl | Cl | CF3 | H | Cl |
A-738 | CH3 | Cl | CF3 | H | Cl |
A-739 | CF3 | Cl | CF3 | H | Cl |
A-740 | OCH3 | Cl | CF3 | H | Cl |
A-741 | F | CH3 | CF3 | H | Cl |
A-742 | Cl | CH3 | CF3 | H | Cl |
A-743 | CH3 | CH3 | CF3 | H | Cl |
A-744 | CF3 | CH3 | CF3 | H | Cl |
A-745 | OCH3 | CH3 | CF3 | H | Cl |
A-746 | F | CF3 | CF3 | H | Cl |
A-747 | Cl | CF3 | CF3 | H | Cl |
A-748 | CH3 | CF3 | CF3 | H | Cl |
A-749 | CF3 | CF3 | CF3 | H | Cl |
A-750 | OCH3 | CF3 | CF3 | H | Cl |
A-751 | F | H | H | F | Cl |
A-752 | Cl | H | H | F | Cl |
A-753 | CH3 | H | H | F | Cl |
A-754 | CF3 | H | H | F | Cl |
A-755 | OCH3 | H | H | F | Cl |
A-756 | F | F | H | F | Cl |
A-757 | Cl | F | H | F | Cl |
A-758 | CH3 | F | H | F | Cl |
A-759 | CF3 | F | H | F | Cl |
A-760 | OCH3 | F | H | F | Cl |
A-761 | F | Cl | H | F | Cl |
A-762 | Cl | Cl | H | F | Cl |
A-763 | CH3 | Cl | H | F | Cl |
A-764 | CF3 | Cl | H | F | Cl |
A-765 | OCH3 | Cl | H | F | Cl |
A-766 | F | CH3 | H | F | Cl |
A-767 | Cl | CH3 | H | F | Cl |
A-768 | CH3 | CH3 | H | F | Cl |
A-769 | CF3 | CH3 | H | F | Cl |
A-770 | OCH3 | CH3 | H | F | Cl |
A-771 | F | CF3 | H | F | Cl |
A-772 | Cl | CF3 | H | F | Cl |
A-773 | CH3 | CF3 | H | F | Cl |
A-774 | CF3 | CF3 | H | F | Cl |
A-775 | OCH3 | CF3 | H | F | Cl |
A-776 | F | H | F | F | Cl |
A-777 | Cl | H | F | F | Cl |
A-778 | CH3 | H | F | F | Cl |
A-779 | CF3 | H | F | F | Cl |
A-780 | OCH3 | H | F | F | Cl |
A-781 | F | F | F | F | Cl |
A-782 | Cl | F | F | F | Cl |
A-783 | CH3 | F | F | F | Cl |
A-784 | CF3 | F | F | F | Cl |
A-785 | OCH3 | F | F | F | Cl |
A-786 | F | Cl | F | F | Cl |
A-787 | Cl | Cl | F | F | Cl |
A-788 | CH3 | Cl | F | F | Cl |
A-789 | CF3 | Cl | F | F | Cl |
A-790 | OCH3 | Cl | F | F | Cl |
A-791 | F | CH3 | F | F | Cl |
A-792 | Cl | CH3 | F | F | Cl |
A-793 | CH3 | CH3 | F | F | Cl |
A-794 | CF3 | CH3 | F | F | Cl |
A-795 | OCH3 | CH3 | F | F | Cl |
A-796 | F | CF3 | F | F | Cl |
A-797 | Cl | CF3 | F | F | Cl |
A-798 | CH3 | CF3 | F | F | Cl |
A-799 | CF3 | CF3 | F | F | Cl |
A-800 | OCH3 | CF3 | F | F | Cl |
A-801 | F | H | Cl | F | Cl |
A-802 | Cl | H | Cl | F | Cl |
A-803 | CH3 | H | Cl | F | Cl |
A-804 | CF3 | H | Cl | F | Cl |
A-805 | OCH3 | H | Cl | F | Cl |
A-806 | F | F | Cl | F | Cl |
A-807 | Cl | F | Cl | F | Cl |
A-808 | CH3 | F | Cl | F | Cl |
A-809 | CF3 | F | Cl | F | Cl |
A-810 | OCH3 | F | Cl | F | Cl |
A-811 | F | Cl | Cl | F | Cl |
A-812 | Cl | Cl | Cl | F | Cl |
A-813 | CH3 | Cl | Cl | F | Cl |
A-814 | CF3 | Cl | Cl | F | Cl |
A-815 | OCH3 | Cl | Cl | F | Cl |
A-816 | F | CH3 | Cl | F | Cl |
A-817 | Cl | CH3 | Cl | F | Cl |
A-818 | CH3 | CH3 | Cl | F | Cl |
A-819 | CF3 | CH3 | Cl | F | Cl |
A-820 | OCH3 | CH3 | Cl | F | Cl |
A-821 | F | CF3 | Cl | F | Cl |
A-822 | Cl | CF3 | Cl | F | Cl |
A-823 | CH3 | CF3 | Cl | F | Cl |
A-824 | CF3 | CF3 | Cl | F | Cl |
A-825 | OCH3 | CF3 | Cl | F | Cl |
A-826 | F | H | CH3 | F | Cl |
A-827 | Cl | H | CH3 | F | Cl |
A-828 | CH3 | H | CH3 | F | Cl |
A-829 | CF3 | H | CH3 | F | Cl |
A-830 | OCH3 | H | CH3 | F | Cl |
A-831 | F | F | CH3 | F | Cl |
A-832 | Cl | F | CH3 | F | Cl |
A-833 | CH3 | F | CH3 | F | Cl |
A-834 | CF3 | F | CH3 | F | Cl |
A-835 | OCH3 | F | CH3 | F | Cl |
A-836 | F | Cl | CH3 | F | Cl |
A-837 | Cl | Cl | CH3 | F | Cl |
A-838 | CH3 | Cl | CH3 | F | Cl |
A-839 | CF3 | Cl | CH3 | F | Cl |
A-840 | OCH3 | Cl | CH3 | F | Cl |
A-841 | F | CH3 | CH3 | F | Cl |
A-842 | Cl | CH3 | CH3 | F | Cl |
A-843 | CH3 | CH3 | CH3 | F | Cl |
A-844 | CF3 | CH3 | CH3 | F | Cl |
A-845 | OCH3 | CH3 | CH3 | F | Cl |
A-846 | F | CF3 | CH3 | F | Cl |
A-847 | Cl | CF3 | CH3 | F | Cl |
A-848 | CH3 | CF3 | CH3 | F | Cl |
A-849 | CF3 | CF3 | CH3 | F | Cl |
A-850 | OCH3 | CF3 | CH3 | F | Cl |
A-851 | F | H | CF3 | F | Cl |
A-852 | Cl | H | CF3 | F | Cl |
A-853 | CH3 | H | CF3 | F | Cl |
A-854 | CF3 | H | CF3 | F | Cl |
A-855 | OCH3 | H | CF3 | F | Cl |
A-856 | F | F | CF3 | F | Cl |
A-857 | Cl | F | CF3 | F | Cl |
A-858 | CH3 | F | CF3 | F | Cl |
A-859 | CF3 | F | CF3 | F | Cl |
A-860 | OCH3 | F | CF3 | F | Cl |
A-861 | F | Cl | CF3 | F | Cl |
A-862 | Cl | Cl | CF3 | F | Cl |
A-863 | CH3 | Cl | CF3 | F | Cl |
A-864 | CF3 | Cl | CF3 | F | Cl |
A-865 | OCH3 | Cl | CF3 | F | Cl |
A-866 | F | CH3 | CF3 | F | Cl |
A-867 | Cl | CH3 | CF3 | F | Cl |
A-868 | CH3 | CH3 | CF3 | F | Cl |
A-869 | CF3 | CH3 | CF3 | F | Cl |
A-870 | OCH3 | CH3 | CF3 | F | Cl |
A-871 | F | CF3 | CF3 | F | Cl |
A-872 | Cl | CF3 | CF3 | F | Cl |
A-873 | CH3 | CF3 | CF3 | F | Cl |
A-874 | CF3 | CF3 | CF3 | F | Cl |
A-875 | OCH3 | CF3 | CF3 | F | Cl |
A-876 | F | H | H | Cl | Cl |
A-877 | Cl | H | H | Cl | Cl |
A-878 | CH3 | H | H | Cl | Cl |
A-879 | CF3 | H | H | Cl | Cl |
A-880 | OCH3 | H | H | Cl | Cl |
A-881 | F | F | H | Cl | Cl |
A-882 | Cl | F | H | Cl | Cl |
A-883 | CH3 | F | H | Cl | Cl |
A-884 | CF3 | F | H | Cl | Cl |
A-885 | OCH3 | F | H | Cl | Cl |
A-886 | F | Cl | H | Cl | Cl |
A-887 | Cl | Cl | H | Cl | Cl |
A-888 | CH3 | Cl | H | Cl | Cl |
A-889 | CF3 | Cl | H | Cl | Cl |
A-890 | OCH3 | Cl | H | Cl | Cl |
A-891 | F | CH3 | H | Cl | Cl |
A-892 | Cl | CH3 | H | Cl | Cl |
A-893 | CH3 | CH3 | H | Cl | Cl |
A-894 | CF3 | CH3 | H | Cl | Cl |
A-895 | OCH3 | CH3 | H | Cl | Cl |
A-896 | F | CF3 | H | Cl | Cl |
A-897 | Cl | CF3 | H | Cl | Cl |
A-898 | CH3 | CF3 | H | Cl | Cl |
A-899 | CF3 | CF3 | H | Cl | Cl |
A-900 | OCH3 | CF3 | H | Cl | Cl |
A-901 | F | H | F | Cl | Cl |
A-902 | Cl | H | F | Cl | Cl |
A-903 | CH3 | H | F | Cl | Cl |
A-904 | CF3 | H | F | Cl | Cl |
A-905 | OCH3 | H | F | Cl | Cl |
A-906 | F | F | F | Cl | Cl |
A-907 | Cl | F | F | Cl | Cl |
A-908 | CH3 | F | F | Cl | Cl |
A-909 | CF3 | F | F | Cl | Cl |
A-910 | OCH3 | F | F | Cl | Cl |
A-911 | F | Cl | F | Cl | Cl |
A-912 | Cl | Cl | F | Cl | Cl |
A-913 | CH3 | Cl | F | Cl | Cl |
A-914 | CF3 | Cl | F | Cl | Cl |
A-915 | OCH3 | Cl | F | Cl | Cl |
A-916 | F | CH3 | F | Cl | Cl |
A-917 | Cl | CH3 | F | Cl | Cl |
A-918 | CH3 | CH3 | F | Cl | Cl |
A-919 | CF3 | CH3 | F | Cl | Cl |
A-920 | OCH3 | CH3 | F | Cl | Cl |
A-921 | F | CF3 | F | Cl | Cl |
A-922 | Cl | CF3 | F | Cl | Cl |
A-923 | CH3 | CF3 | F | Cl | Cl |
A-924 | CF3 | CF3 | F | Cl | Cl |
A-925 | OCH3 | CF3 | F | Cl | Cl |
A-926 | F | H | Cl | Cl | Cl |
A-927 | Cl | H | Cl | Cl | Cl |
A-928 | CH3 | H | Cl | Cl | Cl |
A-929 | CF3 | H | Cl | Cl | Cl |
A-930 | OCH3 | H | Cl | Cl | Cl |
A-931 | F | F | Cl | Cl | Cl |
A-932 | Cl | F | Cl | Cl | Cl |
A-933 | CH3 | F | Cl | Cl | Cl |
A-934 | CF3 | F | Cl | Cl | Cl |
A-935 | OCH3 | F | Cl | Cl | Cl |
A-936 | F | Cl | Cl | Cl | Cl |
A-937 | Cl | Cl | Cl | Cl | Cl |
A-938 | CH3 | Cl | Cl | Cl | Cl |
A-939 | CF3 | Cl | Cl | Cl | Cl |
A-940 | OCH3 | Cl | Cl | Cl | Cl |
A-941 | F | CH3 | Cl | Cl | Cl |
A-942 | Cl | CH3 | Cl | Cl | Cl |
A-943 | CH3 | CH3 | Cl | Cl | Cl |
A-944 | CF3 | CH3 | Cl | Cl | Cl |
A-945 | OCH3 | CH3 | Cl | Cl | Cl |
A-946 | F | CF3 | Cl | Cl | Cl |
A-947 | Cl | CF3 | Cl | Cl | Cl |
A-948 | CH3 | CF3 | Cl | Cl | Cl |
A-949 | CF3 | CF3 | Cl | Cl | Cl |
A-950 | OCH3 | CF3 | Cl | Cl | Cl |
A-951 | F | H | CH3 | Cl | Cl |
A-952 | Cl | H | CH3 | Cl | Cl |
A-953 | CH3 | H | CH3 | Cl | Cl |
A-954 | CF3 | H | CH3 | Cl | Cl |
A-955 | OCH3 | H | CH3 | Cl | Cl |
A-956 | F | F | CH3 | Cl | Cl |
A-957 | Cl | F | CH3 | Cl | Cl |
A-958 | CH3 | F | CH3 | Cl | Cl |
A-959 | CF3 | F | CH3 | Cl | Cl |
A-960 | OCH3 | F | CH3 | Cl | Cl |
A-961 | F | Cl | CH3 | Cl | Cl |
A-962 | Cl | Cl | CH3 | Cl | Cl |
A-963 | CH3 | Cl | CH3 | Cl | Cl |
A-964 | CF3 | Cl | CH3 | Cl | Cl |
A-965 | OCH3 | Cl | CH3 | Cl | Cl |
A-966 | F | CH3 | CH3 | Cl | Cl |
A-967 | Cl | CH3 | CH3 | Cl | Cl |
A-968 | CH3 | CH3 | CH3 | Cl | Cl |
A-969 | CF3 | CH3 | CH3 | Cl | Cl |
A-970 | OCH3 | CH3 | CH3 | Cl | Cl |
A-971 | F | CF3 | CH3 | Cl | Cl |
A-972 | Cl | CF3 | CH3 | Cl | Cl |
A-973 | CH3 | CF3 | CH3 | Cl | Cl |
A-974 | CF3 | CF3 | CH3 | Cl | Cl |
A-975 | OCH3 | CF3 | CH3 | Cl | Cl |
A-976 | F | H | CF3 | Cl | Cl |
A-977 | Cl | H | CF3 | Cl | Cl |
A-978 | CH3 | H | CF3 | Cl | Cl |
A-979 | CF3 | H | CF3 | Cl | Cl |
A-980 | OCH3 | H | CF3 | Cl | Cl |
A-981 | F | F | CF3 | Cl | Cl |
A-982 | Cl | F | CF3 | Cl | Cl |
A-983 | CH3 | F | CF3 | Cl | Cl |
A-984 | CF3 | F | CF3 | Cl | Cl |
A-985 | OCH3 | F | CF3 | Cl | Cl |
A-986 | F | Cl | CF3 | Cl | Cl |
A-987 | Cl | Cl | CF3 | Cl | Cl |
A-988 | CH3 | Cl | CF3 | Cl | Cl |
A-989 | CF3 | Cl | CF3 | Cl | Cl |
A-990 | OCH3 | Cl | CF3 | Cl | Cl |
A-991 | F | CH3 | CF3 | Cl | Cl |
A-992 | Cl | CH3 | CF3 | Cl | Cl |
A-993 | CH3 | CH3 | CF3 | Cl | Cl |
A-994 | CF3 | CH3 | CF3 | Cl | Cl |
A-995 | OCH3 | CH3 | CF3 | Cl | Cl |
A-996 | F | CF3 | CF3 | Cl | Cl |
A-997 | Cl | CF3 | CF3 | Cl | Cl |
A-998 | CH3 | CF3 | CF3 | Cl | Cl |
A-999 | CF3 | CF3 | CF3 | Cl | Cl |
A-1000 | OCH3 | CF3 | CF3 | Cl | Cl |
A-1001 | F | H | H | CH3 | Cl |
A-1002 | Cl | H | H | CH3 | Cl |
A-1003 | CH3 | H | H | CH3 | Cl |
A-1004 | CF3 | H | H | CH3 | Cl |
A-1005 | OCH3 | H | H | CH3 | Cl |
A-1006 | F | F | H | CH3 | Cl |
A-1007 | Cl | F | H | CH3 | Cl |
A-1008 | CH3 | F | H | CH3 | Cl |
A-1009 | CF3 | F | H | CH3 | Cl |
A-1010 | OCH3 | F | H | CH3 | Cl |
A-1011 | F | Cl | H | CH3 | Cl |
A-1012 | Cl | Cl | H | CH3 | Cl |
A-1013 | CH3 | Cl | H | CH3 | Cl |
A-1014 | CF3 | Cl | H | CH3 | Cl |
A-1015 | OCH3 | Cl | H | CH3 | Cl |
A-1016 | F | CH3 | H | CH3 | Cl |
A-1017 | Cl | CH3 | H | CH3 | Cl |
A-1018 | CH3 | CH3 | H | CH3 | Cl |
A-1019 | CF3 | CH3 | H | CH3 | Cl |
A-1020 | OCH3 | CH3 | H | CH3 | Cl |
A-1021 | F | CF3 | H | CH3 | Cl |
A-1022 | Cl | CF3 | H | CH3 | Cl |
A-1023 | CH3 | CF3 | H | CH3 | Cl |
A-1024 | CF3 | CF3 | H | CH3 | Cl |
A-1025 | OCH3 | CF3 | H | CH3 | Cl |
A-1026 | F | H | F | CH3 | Cl |
A-1027 | Cl | H | F | CH3 | Cl |
A-1028 | CH3 | H | F | CH3 | Cl |
A-1029 | CF3 | H | F | CH3 | Cl |
A-1030 | OCH3 | H | F | CH3 | Cl |
A-1031 | F | F | F | CH3 | Cl |
A-1032 | Cl | F | F | CH3 | Cl |
A-1033 | CH3 | F | F | CH3 | Cl |
A-1034 | CF3 | F | F | CH3 | Cl |
A-1035 | OCH3 | F | F | CH3 | Cl |
A-1036 | F | Cl | F | CH3 | Cl |
A-1037 | Cl | Cl | F | CH3 | Cl |
A-1038 | CH3 | Cl | F | CH3 | Cl |
A-1039 | CF3 | Cl | F | CH3 | Cl |
A-1040 | OCH3 | Cl | F | CH3 | Cl |
A-1041 | F | CH3 | F | CH3 | Cl |
A-1042 | Cl | CH3 | F | CH3 | Cl |
A-1043 | CH3 | CH3 | F | CH3 | Cl |
A-1044 | CF3 | CH3 | F | CH3 | Cl |
A-1045 | OCH3 | CH3 | F | CH3 | Cl |
A-1046 | F | CF3 | F | CH3 | Cl |
A-1047 | Cl | CF3 | F | CH3 | Cl |
A-1048 | CH3 | CF3 | F | CH3 | Cl |
A-1049 | CF3 | CF3 | F | CH3 | Cl |
A-1050 | OCH3 | CF3 | F | CH3 | Cl |
A-1051 | F | H | Cl | CH3 | Cl |
A-1052 | Cl | H | Cl | CH3 | Cl |
A-1053 | CH3 | H | Cl | CH3 | Cl |
A-1054 | CF3 | H | Cl | CH3 | Cl |
A-1055 | OCH3 | H | Cl | CH3 | Cl |
A-1056 | F | F | Cl | CH3 | Cl |
A-1057 | Cl | F | Cl | CH3 | Cl |
A-1058 | CH3 | F | Cl | CH3 | Cl |
A-1059 | CF3 | F | Cl | CH3 | Cl |
A-1060 | OCH3 | F | Cl | CH3 | Cl |
A-1061 | F | Cl | Cl | CH3 | Cl |
A-1062 | Cl | Cl | Cl | CH3 | Cl |
A-1063 | CH3 | Cl | Cl | CH3 | Cl |
A-1064 | CF3 | Cl | Cl | CH3 | Cl |
A-1065 | OCH3 | Cl | Cl | CH3 | Cl |
A-1066 | F | CH3 | Cl | CH3 | Cl |
A-1067 | Cl | CH3 | Cl | CH3 | Cl |
A-1068 | CH3 | CH3 | Cl | CH3 | Cl |
A-1069 | CF3 | CH3 | Cl | CH3 | Cl |
A-1070 | OCH3 | CH3 | Cl | CH3 | Cl |
A-1071 | F | CF3 | Cl | CH3 | Cl |
A-1072 | Cl | CF3 | Cl | CH3 | Cl |
A-1073 | CH3 | CF3 | Cl | CH3 | Cl |
A-1074 | CF3 | CF3 | Cl | CH3 | Cl |
A-1075 | OCH3 | CF3 | Cl | CH3 | Cl |
A-1076 | F | H | CH3 | CH3 | Cl |
A-1077 | Cl | H | CH3 | CH3 | Cl |
A-1078 | CH3 | H | CH3 | CH3 | Cl |
A-1079 | CF3 | H | CH3 | CH3 | Cl |
A-1080 | OCH3 | H | CH3 | CH3 | Cl |
A-1081 | F | F | CH3 | CH3 | Cl |
A-1082 | Cl | F | CH3 | CH3 | Cl |
A-1083 | CH3 | F | CH3 | CH3 | Cl |
A-1084 | CF3 | F | CH3 | CH3 | Cl |
A-1085 | OCH3 | F | CH3 | CH3 | Cl |
A-1086 | F | Cl | CH3 | CH3 | Cl |
A-1087 | Cl | Cl | CH3 | CH3 | Cl |
A-1088 | CH3 | C | CH3 | CH3 | Cl |
A-1089 | CF3 | Cl | CH3 | CH3 | Cl |
A-1090 | OCH3 | Cl | CH3 | CH3 | Cl |
A-1091 | F | CH3 | CH3 | CH3 | Cl |
A-1092 | Cl | CH3 | CH3 | CH3 | Cl |
A-1093 | CH3 | CH3 | CH3 | CH3 | Cl |
A-1094 | CF3 | CH3 | CH3 | CH3 | Cl |
A-1095 | OCH3 | CH3 | CH3 | CH3 | Cl |
A-1096 | F | CF3 | CH3 | CH3 | Cl |
A-1097 | Cl | CF3 | CH3 | CH3 | Cl |
A-1098 | CH3 | CF3 | CH3 | CH3 | Cl |
A-1099 | CF3 | CF3 | CH3 | CH3 | Cl |
A-1100 | OCH3 | CF3 | CH3 | CH3 | Ck |
A-1101 | F | H | CF3 | CH3 | Cl |
A-1102 | Cl | H | CF3 | CH3 | Cl |
A-1103 | CH3 | H | CF3 | CH3 | Cl |
A-1104 | CF3 | H | CF3 | CH3 | Cl |
A-1105 | OCH3 | H | CF3 | CH3 | Cl |
A-1106 | F | F | CF3 | CH3 | Cl |
A-1107 | Cl | F | CF3 | CH3 | Cl |
A-1108 | CH3 | F | CF3 | CH3 | Cl |
A-1109 | CF3 | F | CF3 | CH3 | Cl |
A-1110 | OCH3 | F | CF3 | CH3 | Cl |
A-1111 | F | Cl | CF3 | CH3 | Cl |
A-1112 | Cl | Cl | CF3 | CH3 | Cl |
A-1113 | CH3 | Cl | CF3 | CH3 | Cl |
A-1114 | CF3 | Cl | CF3 | CH3 | Cl |
A-1115 | OCH3 | Cl | CF3 | CH3 | Cl |
A-1116 | F | CH3 | CF3 | CH3 | Cl |
A-1117 | Cl | CH3 | CF3 | CH3 | Cl |
A-1118 | CH3 | CH3 | CF3 | CH3 | Cl |
A-1119 | CF3 | CH3 | CF3 | CH3 | Cl |
A-1120 | OCH3 | CH3 | CF3 | CH3 | Cl |
A-1121 | F | CF3 | CF3 | CH3 | Cl |
A-1122 | Cl | CF3 | CF3 | CH3 | Cl |
A-1123 | CH3 | CF3 | CF3 | CH3 | Cl |
A-1124 | CF3 | CF3 | CF3 | CH3 | Cl |
A-1125 | OCH3 | CF3 | CF3 | CH3 | Cl |
A-1126 | F | H | H | CF3 | Cl |
A-1127 | Cl | H | H | CF3 | Cl |
A-1128 | CH3 | H | H | CF3 | Cl |
A-1129 | CF3 | H | H | CF3 | Cl |
A-1130 | OCH3 | H | H | CF3 | Cl |
A-1131 | F | F | H | CF3 | Cl |
A-1132 | Cl | F | H | CF3 | Cl |
A-1133 | CH3 | F | H | CF3 | Cl |
A-1134 | CF3 | F | H | CF3 | Cl |
A-1135 | OCH3 | F | H | CF3 | Cl |
A-1136 | F | Cl | H | CF3 | Cl |
A-1137 | Cl | Cl | H | CF3 | Cl |
A-1138 | CH3 | Cl | H | CF3 | Cl |
A-1139 | CF3 | Cl | H | CF3 | Cl |
A-1140 | OCH3 | Cl | H | CF3 | Cl |
A-1141 | F | CH3 | H | CF3 | Cl |
A-1142 | Cl | CH3 | H | CF3 | Cl |
A-1143 | CH3 | CH3 | H | CF3 | Cl |
A-1144 | CF3 | CH3 | H | CF3 | Cl |
A-1145 | OCH3 | CH3 | H | CF3 | Cl |
A-1146 | F | CF3 | H | CF3 | Cl |
A-1147 | Cl | CF3 | H | CF3 | Cl |
A-1148 | CH3 | CF3 | H | CF3 | Cl |
A-1149 | CF3 | CF3 | H | CF3 | Cl |
A-1150 | OCH3 | CF3 | H | CF3 | Cl |
A-1151 | F | H | F | CF3 | Cl |
A-1152 | Cl | H | F | CF3 | Cl |
A-1153 | CH3 | H | F | CF3 | Cl |
A-1154 | CF3 | H | F | CF3 | Cl |
A-1155 | OCH3 | H | F | CF3 | Cl |
A-1156 | F | F | F | CF3 | Cl |
A-1157 | Cl | F | F | CF3 | Cl |
A-1158 | CH3 | F | F | CF3 | Cl |
A-1159 | CF3 | F | F | CF3 | Cl |
A-1160 | OCH3 | F | F | CF3 | Cl |
A-1161 | F | Cl | F | CF3 | Cl |
A-1162 | Cl | Cl | F | CF3 | Cl |
A-1163 | CH3 | Cl | F | CF3 | Cl |
A-1164 | CF3 | Cl | F | CF3 | Cl |
A-1165 | OCH3 | Cl | F | CF3 | Cl |
A-1166 | F | CH3 | F | CF3 | Cl |
A-1167 | Cl | CH3 | F | CF3 | Cl |
A-1168 | CH3 | CH3 | F | CF3 | Cl |
A-1169 | CF3 | CH3 | F | CF3 | Cl |
A-1170 | OCH3 | CH3 | F | CF3 | Cl |
A-1171 | F | CF3 | F | CF3 | Cl |
A-1172 | Cl | CF3 | F | CF3 | Cl |
A-1173 | CH3 | CF3 | F | CF3 | Cl |
A-1174 | CF3 | CF3 | F | CF3 | Cl |
A-1175 | OCH3 | CF3 | F | CF3 | Cl |
A-1176 | F | H | Cl | CF3 | Cl |
A-1177 | Cl | H | Cl | CF3 | Cl |
A-1178 | CH3 | H | Cl | CF3 | Cl |
A-1179 | CF3 | H | Cl | CF3 | Cl |
A-1180 | OCH3 | H | Cl | CF3 | Cl |
A-1181 | F | F | Cl | CF3 | Cl |
A-1182 | Cl | F | Cl | CF3 | Cl |
A-1183 | CH3 | F | Cl | CF3 | Cl |
A-1184 | CF3 | F | Cl | CF3 | Cl |
A-1185 | OCH3 | F | Cl | CF3 | Cl |
A-1186 | F | Cl | Cl | CF3 | Cl |
A-1187 | Cl | Cl | Cl | CF3 | Cl |
A-1188 | CH3 | Cl | Cl | CF3 | Cl |
A-1189 | CF3 | Cl | Cl | CF3 | Cl |
A-1190 | OCH3 | Cl | Cl | CF3 | Cl |
A-1191 | F | CH3 | Cl | CF3 | Cl |
A-1192 | Cl | CH3 | Cl | CF3 | Cl |
A-1193 | CH3 | CH3 | Cl | CF3 | Cl |
A-1194 | CF3 | CH3 | Cl | CF3 | Cl |
A-1195 | OCH3 | CH3 | Cl | CF3 | Cl |
A-1196 | F | CF3 | Cl | CF3 | Cl |
A-1197 | Cl | CF3 | Cl | CF3 | Cl |
A-1198 | CH3 | CF3 | Cl | CF3 | Cl |
A-1199 | CF3 | CF3 | Cl | CF3 | Cl |
A-1200 | OCH3 | CF3 | Cl | CF3 | Cl |
A-1201 | F | H | CH3 | CF3 | Cl |
A-1202 | Cl | H | CH3 | CF3 | Cl |
A-1203 | CH3 | H | CH3 | CF3 | Cl |
A-1204 | CF3 | H | CH3 | CF3 | Cl |
A-1205 | OCH3 | H | CH3 | CF3 | Cl |
A-1206 | F | F | CH3 | CF3 | Cl |
A-1207 | Cl | F | CH3 | CF3 | Cl |
A-1208 | CH3 | F | CH3 | CF3 | Cl |
A-1209 | CF3 | F | CH3 | CF3 | Cl |
A-1210 | OCH3 | F | CH3 | CF3 | Cl |
A-1211 | F | Cl | CH3 | CF3 | Cl |
A-1212 | Cl | Cl | CH3 | CF3 | Cl |
A-1213 | CH3 | Cl | CH3 | CF3 | Cl |
A-1214 | CF3 | Cl | CH3 | CF3 | Cl |
A-1215 | OCH3 | Cl | CH3 | CF3 | Cl |
A-1216 | F | CH3 | CH3 | CF3 | Cl |
A-1217 | Cl | CH3 | CH3 | CF3 | Cl |
A-1218 | CH3 | CH3 | CH3 | CF3 | Cl |
A-1219 | CF3 | CH3 | CH3 | CF3 | Cl |
A-1220 | OCH3 | CH3 | CH3 | CF3 | Cl |
A-1221 | F | CF3 | CH3 | CF3 | Cl |
A-1222 | Cl | CF3 | CH3 | CF3 | Cl |
A-1223 | CH3 | CF3 | CH3 | CF3 | Cl |
A-1224 | CF3 | CF3 | CH3 | CF3 | Cl |
A-1225 | OCH3 | CF3 | CH3 | CF3 | Cl |
A-1226 | F | H | CF3 | CF3 | Cl |
A-1227 | Cl | H | CF3 | CF3 | Cl |
A-1228 | CH3 | H | CF3 | CF3 | Cl |
A-1229 | CF3 | H | CF3 | CF3 | Cl |
A-1230 | OCH3 | H | CF3 | CF3 | Cl |
A-1231 | F | F | CF3 | CF3 | Cl |
A-1232 | Cl | F | CF3 | CF3 | Cl |
A-1233 | CH3 | F | CF3 | CF3 | Cl |
A-1234 | CF3 | F | CF3 | CF3 | Cl |
A-1235 | OCH3 | F | CF3 | CF3 | Cl |
A-1236 | F | Cl | CF3 | CF3 | Cl |
A-1237 | Cl | Cl | CF3 | CF3 | Cl |
A-1238 | CH3 | Cl | CF3 | CF3 | Cl |
A-1239 | CF3 | Cl | CF3 | CF3 | Cl |
A-1240 | OCH3 | Cl | CF3 | CF3 | Cl |
A-1241 | F | CH3 | CF3 | CF3 | Cl |
A-1242 | Cl | CH3 | CF3 | CF3 | Cl |
A-1243 | CH3 | CH3 | CF3 | CF3 | Cl |
A-1244 | CF3 | CH3 | CF3 | CF3 | Cl |
A-1245 | OCH3 | CH3 | CF3 | CF3 | Cl |
A-1246 | F | CF3 | CF3 | CF3 | Cl |
A-1247 | Cl | CF3 | CF3 | CF3 | Cl |
A-1248 | CH3 | CF3 | CF3 | CF3 | Cl |
A-1249 | CF3 | CF3 | CF3 | CF3 | Cl |
A-1250 | OCH3 | CF3 | CF3 | CF3 | Cl |
A-1251 | F | H | H | H | CH3 |
A-1252 | Cl | H | H | H | CH3 |
A-1253 | CH3 | H | H | H | CH3 |
A-1254 | CF3 | H | H | H | CH3 |
A-1255 | OCH3 | H | H | H | CH3 |
A-1256 | F | F | H | H | CH3 |
A-1257 | Cl | F | H | H | CH3 |
A-1258 | CH3 | F | H | H | CH3 |
A-1259 | CF3 | F | H | H | CH3 |
A-1260 | OCH3 | F | H | H | CH3 |
A-1261 | F | Cl | H | H | CH3 |
A-1262 | Cl | Cl | H | H | CH3 |
A-1263 | CH3 | Cl | H | H | CH3 |
A-1264 | CF3 | Cl | H | H | CH3 |
A-1265 | OCH3 | Cl | H | H | CH3 |
A-1266 | F | CH3 | H | H | CH3 |
A-1267 | Cl | CH3 | H | H | CH3 |
A-1268 | CH3 | CH3 | H | H | CH3 |
A-1269 | CF3 | CH3 | H | H | CH3 |
A-1270 | OCH3 | CH3 | H | H | CH3 |
A-1271 | F | CF3 | H | H | CH3 |
A-1272 | Cl | CF3 | H | H | CH3 |
A-1273 | CH3 | CF3 | H | H | CH3 |
A-1274 | CF3 | CF3 | H | H | CH3 |
A-1275 | OCH3 | CF3 | H | H | CH3 |
A-1276 | F | H | F | H | CH3 |
A-1277 | Cl | H | F | H | CH3 |
A-1278 | CH3 | H | F | H | CH3 |
A-1279 | CF3 | H | F | H | CH3 |
A-1280 | OCH3 | H | F | H | CH3 |
A-1281 | F | F | F | H | CH3 |
A-1282 | Cl | F | F | H | CH3 |
A-1283 | CH3 | F | F | H | CH3 |
A-1284 | CF3 | F | F | H | CH3 |
A-1285 | OCH3 | F | F | H | CH3 |
A-1286 | F | Cl | F | H | CH3 |
A-1287 | Cl | Cl | F | H | CH3 |
A-1288 | CH3 | Cl | F | H | CH3 |
A-1289 | CF3 | Cl | F | H | CH3 |
A-1290 | OCH3 | Cl | F | H | CH3 |
A-1291 | F | CH3 | F | H | CH3 |
A-1292 | Cl | CH3 | F | H | CH3 |
A-1293 | CH3 | CH3 | F | H | CH3 |
A-1294 | CF3 | CH3 | F | H | CH3 |
A-1295 | OCH3 | CH3 | F | H | CH3 |
A-1296 | F | CF3 | F | H | CH3 |
A-1297 | Cl | CF3 | F | H | CH3 |
A-1298 | CH3 | CF3 | F | H | CH3 |
A-1299 | CF3 | CF3 | F | H | CH3 |
A-1300 | OCH3 | CF3 | F | H | CH3 |
A-1301 | F | H | Cl | H | CH3 |
A-1302 | Cl | H | Cl | H | CH3 |
A-1303 | CH3 | H | Cl | H | CH3 |
A-1304 | CF3 | H | Cl | H | CH3 |
A-1305 | OCH3 | H | Cl | H | CH3 |
A-1306 | F | F | Cl | H | CH3 |
A-1307 | Cl | F | Cl | H | CH3 |
A-1308 | CH3 | F | Cl | H | CH3 |
A-1309 | CF3 | F | Cl | H | CH3 |
A-1310 | OCH3 | F | Cl | H | CH3 |
A-1311 | F | Cl | Cl | H | CH3 |
A-1312 | Cl | Cl | Cl | H | CH3 |
A-1313 | CH3 | Cl | Cl | H | CH3 |
A-1314 | CF3 | Cl | Cl | H | CH3 |
A-1315 | OCH3 | Cl | Cl | H | CH3 |
A-1316 | F | CH3 | Cl | H | CH3 |
A-1317 | Cl | CH3 | Cl | H | CH3 |
A-1318 | CH3 | CH3 | Cl | H | CH3 |
A-1319 | CF3 | CH3 | Cl | H | CH3 |
A-1320 | OCH3 | CH3 | Cl | H | CH3 |
A-1321 | F | CF3 | Cl | H | CH3 |
A-1322 | Cl | CF3 | Cl | H | CH3 |
A-1323 | CH3 | CF3 | Cl | H | CH3 |
A-1324 | CF3 | CF3 | Cl | H | CH3 |
A-1325 | OCH3 | CF3 | Cl | H | CH3 |
A-1326 | F | H | CH3 | H | CH3 |
A-1327 | Cl | H | CH3 | H | CH3 |
A-1328 | CH3 | H | CH3 | H | CH3 |
A-1329 | CF3 | H | CH3 | H | CH3 |
A-1330 | OCH3 | H | CH3 | H | CH3 |
A-1331 | F | F | CH3 | H | CH3 |
A-1332 | Cl | F | CH3 | H | CH3 |
A-1333 | CH3 | F | CH3 | H | CH3 |
A-1334 | CF3 | F | CH3 | H | CH3 |
A-1335 | OCH3 | F | CH3 | H | CH3 |
A-1336 | F | Cl | CH3 | H | CH3 |
A-1337 | Cl | Cl | CH3 | H | CH3 |
A-1338 | CH3 | Cl | CH3 | H | CH3 |
A-1339 | CF3 | Cl | CH3 | H | CH3 |
A-1340 | OCH3 | Cl | CH3 | H | CH3 |
A-1341 | F | CH3 | CH3 | H | CH3 |
A-1342 | Cl | CH3 | CH3 | H | CH3 |
A-1343 | CH3 | CH3 | CH3 | H | CH3 |
A-1344 | CF3 | CH3 | CH3 | H | CH3 |
A-1345 | OCH3 | CH3 | CH3 | H | CH3 |
A-1346 | F | CF3 | CH3 | H | CH3 |
A-1347 | Cl | CF3 | CH3 | H | CH3 |
A-1348 | CH3 | CF3 | CH3 | H | CH3 |
A-1349 | CF3 | CF3 | CH3 | H | CH3 |
A-1350 | OCH3 | CF3 | CH3 | H | CH3 |
A-1351 | F | H | CF3 | H | CH3 |
A-1352 | Cl | H | CF3 | H | CH3 |
A-1353 | CH3 | H | CF3 | H | CH3 |
A-1354 | CF3 | H | CF3 | H | CH3 |
A-1355 | OCH3 | H | CF3 | H | CH3 |
A-1356 | F | F | CF3 | H | CH3 |
A-1357 | Cl | F | CF3 | H | CH3 |
A-1358 | CH3 | F | CF3 | H | CH3 |
A-1359 | CF3 | F | CF3 | H | CH3 |
A-1360 | OCH3 | F | CF3 | H | CH3 |
A-1361 | F | Cl | CF3 | H | CH3 |
A-1362 | Cl | Cl | CF3 | H | CH3 |
A-1363 | CH3 | Cl | CF3 | H | CH3 |
A-1364 | CF3 | Cl | CF3 | H | CH3 |
A-1365 | OCH3 | Cl | CF3 | H | CH3 |
A-1366 | F | CH3 | CF3 | H | CH3 |
A-1367 | Cl | CH3 | CF3 | H | CH3 |
A-1368 | CH3 | CH3 | CF3 | H | CH3 |
A-1369 | CF3 | CH3 | CF3 | H | CH3 |
A-1370 | OCH3 | CH3 | CF3 | H | CH3 |
A-1371 | F | CF3 | CF3 | H | CH3 |
A-1372 | Cl | CF3 | CF3 | H | CH3 |
A-1373 | CH3 | CF3 | CF3 | H | CH3 |
A-1374 | CF3 | CF3 | CF3 | H | CH3 |
A-1375 | OCH3 | CF3 | CF3 | H | CH3 |
A-1376 | F | H | H | F | CH3 |
A-1377 | Cl | H | H | F | CH3 |
A-1378 | CH3 | H | H | F | CH3 |
A-1379 | CF3 | H | H | F | CH3 |
A-1380 | OCH3 | H | H | F | CH3 |
A-1381 | F | F | H | F | CH3 |
A-1382 | Cl | F | H | F | CH3 |
A-1383 | CH3 | F | H | F | CH3 |
A-1384 | CF3 | F | H | F | CH3 |
A-1385 | OCH3 | F | H | F | CH3 |
A-1386 | F | Cl | H | F | CH3 |
A-1387 | Cl | Cl | H | F | CH3 |
A-1388 | CH3 | Cl | H | F | CH3 |
A-1389 | CF3 | Cl | H | F | CH3 |
A-1390 | OCH3 | Cl | H | F | CH3 |
A-1391 | F | CH3 | H | F | CH3 |
A-1392 | Cl | CH3 | H | F | CH3 |
A-1393 | CH3 | CH3 | H | F | CH3 |
A-1394 | CF3 | CH3 | H | F | CH3 |
A-1395 | OCH3 | CH3 | H | F | CH3 |
A-1396 | F | CF3 | H | F | CH3 |
A-1397 | Cl | CF3 | H | F | CH3 |
A-1398 | CH3 | CF3 | H | F | CH3 |
A-1399 | CF3 | CF3 | H | F | CH3 |
A-1400 | OCH3 | CF3 | H | F | CH3 |
A-1401 | F | H | F | F | CH3 |
A-1402 | Cl | H | F | F | CH3 |
A-1403 | CH3 | H | F | F | CH3 |
A-1404 | CF3 | H | F | F | CH3 |
A-1405 | OCH3 | H | F | F | CH3 |
A-1406 | F | F | F | F | CH3 |
A-1407 | Cl | F | F | F | CH3 |
A-1408 | CH3 | F | F | F | CH3 |
A-1409 | CF3 | F | F | F | CH3 |
A-1410 | OCH3 | F | F | F | CH3 |
A-1411 | F | Cl | F | F | CH3 |
A-1412 | Cl | Cl | F | F | CH3 |
A-1413 | CH3 | Cl | F | F | CH3 |
A-1414 | CF3 | Cl | F | F | CH3 |
A-1415 | OCH3 | Cl | F | F | CH3 |
A-1416 | F | CH3 | F | F | CH3 |
A-1417 | Cl | CH3 | F | F | CH3 |
A-1418 | CH3 | CH3 | F | F | CH3 |
A-1419 | CF3 | CH3 | F | F | CH3 |
A-1420 | OCH3 | CH3 | F | F | CH3 |
A-1421 | F | CF3 | F | F | CH3 |
A-1422 | Cl | CF3 | F | F | CH3 |
A-1423 | CH3 | CF3 | F | F | CH3 |
A-1424 | CF3 | CF3 | F | F | CH3 |
A-1425 | OCH3 | CF3 | F | F | CH3 |
A-1426 | F | H | Cl | F | CH3 |
A-1427 | Cl | H | Cl | F | CH3 |
A-1428 | CH3 | H | Cl | F | CH3 |
A-1429 | CF3 | H | Cl | F | CH3 |
A-1430 | OCH3 | H | Cl | F | CH3 |
A-1431 | F | F | Cl | F | CH3 |
A-1432 | Cl | F | Cl | F | CH3 |
A-1433 | CH3 | F | Cl | F | CH3 |
A-1434 | CF3 | F | Cl | F | CH3 |
A-1435 | OCH3 | F | Cl | F | CH3 |
A-1436 | F | Cl | Cl | F | CH3 |
A-1437 | Cl | Cl | Cl | F | CH3 |
A-1438 | CH3 | Cl | Cl | F | CH3 |
A-1439 | CF3 | Cl | Cl | F | CH3 |
A-1440 | OCH3 | Cl | Cl | F | CH3 |
A-1441 | F | CH3 | Cl | F | CH3 |
A-1442 | Cl | CH3 | Cl | F | CH3 |
A-1443 | CH3 | CH3 | Cl | F | CH3 |
A-1444 | CF3 | CH3 | Cl | F | CH3 |
A-1445 | OCH3 | CH3 | Cl | F | CH3 |
A-1446 | F | CF3 | Cl | F | CH3 |
A-1447 | Cl | CF3 | Cl | F | CH3 |
A-1448 | CH3 | CF3 | Cl | F | CH3 |
A-1449 | CF3 | CF3 | Cl | F | CH3 |
A-1450 | OCH3 | CF3 | Cl | F | CH3 |
A-1451 | F | H | CH3 | F | CH3 |
A-1452 | Cl | H | CH3 | F | CH3 |
A-1453 | CH3 | H | CH3 | F | CH3 |
A-1454 | CF3 | H | CH3 | F | CH3 |
A-1455 | OCH3 | H | CH3 | F | CH3 |
A-1456 | F | F | CH3 | F | CH3 |
A-1457 | Cl | F | CH3 | F | CH3 |
A-1458 | CH3 | F | CH3 | F | CH3 |
A-1459 | CF3 | F | CH3 | F | CH3 |
A-1460 | OCH3 | F | CH3 | F | CH3 |
A-1461 | F | Cl | CH3 | F | CH3 |
A-1462 | Cl | Cl | CH3 | F | CH3 |
A-1463 | CH3 | Cl | CH3 | F | CH3 |
A-1464 | CF3 | Cl | CH3 | F | CH3 |
A-1465 | OCH3 | Cl | CH3 | F | CH3 |
A-1466 | F | CH3 | CH3 | F | CH3 |
A-1467 | Cl | CH3 | CH3 | F | CH3 |
A-1468 | CH3 | CH3 | CH3 | F | CH3 |
A-1469 | CF3 | CH3 | CH3 | F | CH3 |
A-1470 | OCH3 | CH3 | CH3 | F | CH3 |
A-1471 | F | CF3 | CH3 | F | CH3 |
A-1472 | Cl | CF3 | CH3 | F | CH3 |
A-1473 | CH3 | CF3 | CH3 | F | CH3 |
A-1474 | CF3 | CF3 | CH3 | F | CH3 |
A-1475 | OCH3 | CF3 | CH3 | F | CH3 |
A-1476 | F | H | CF3 | F | CH3 |
A-1477 | Cl | H | CF3 | F | CH3 |
A-1478 | CH3 | H | CF3 | F | CH3 |
A-1479 | CF3 | H | CF3 | F | CH3 |
A-1480 | OCH3 | H | CF3 | F | CH3 |
A-1481 | F | F | CF3 | F | CH3 |
A-1482 | Cl | F | CF3 | F | CH3 |
A-1483 | CH3 | F | CF3 | F | CH3 |
A-1484 | CF3 | F | CF3 | F | CH3 |
A-1485 | OCH3 | F | CF3 | F | CH3 |
A-1486 | F | Cl | CF3 | F | CH3 |
A-1487 | Cl | Cl | CF3 | F | CH3 |
A-1488 | CH3 | Cl | CF3 | F | CH3 |
A-1489 | CF3 | Cl | CF3 | F | CH3 |
A-1490 | OCH3 | Cl | CF3 | F | CH3 |
A-1491 | F | CH3 | CF3 | F | CH3 |
A-1492 | Cl | CH3 | CF3 | F | CH3 |
A-1493 | CH3 | CH3 | CF3 | F | CH3 |
A-1494 | CF3 | CH3 | CF3 | F | CH3 |
A-1495 | OCH3 | CH3 | CF3 | F | CH3 |
A-1496 | F | CF3 | CF3 | F | CH3 |
A-1497 | Cl | CF3 | CF3 | F | CH3 |
A-1498 | CH3 | CF3 | CF3 | F | CH3 |
A-1499 | CF3 | CF3 | CF3 | F | CH3 |
A-1500 | OCH3 | CF3 | CF3 | F | CH3 |
A-1501 | F | H | H | Cl | CH3 |
A-1502 | Cl | H | H | Cl | CH3 |
A-1503 | CH3 | H | H | Cl | CH3 |
A-1504 | CF3 | H | H | Cl | CH3 |
A-1505 | OCH3 | H | H | Cl | CH3 |
A-1506 | F | F | H | Cl | CH3 |
A-1507 | Cl | F | H | Cl | CH3 |
A-1508 | CH3 | F | H | Cl | CH3 |
A-1509 | CF3 | F | H | Cl | CH3 |
A-1510 | OCH3 | F | H | Cl | CH3 |
A-1511 | F | Cl | H | Cl | CH3 |
A-1512 | Cl | Cl | H | Cl | CH3 |
A-1513 | CH3 | Cl | H | Cl | CH3 |
A-1514 | CF3 | Cl | H | Cl | CH3 |
A-1515 | OCH3 | C | H | Cl | CH3 |
A-1516 | F | CH3 | H | Cl | CH3 |
A-1517 | Cl | CH3 | H | Cl | CH3 |
A-1518 | CH3 | CH3 | H | Cl | CH3 |
A-1519 | CF3 | CH3 | H | Cl | CH3 |
A-1520 | OCH3 | CH3 | H | Cl | CH3 |
A-1521 | F | CF3 | H | Cl | CH3 |
A-1522 | Cl | CF3 | H | Cl | CH3 |
A-1523 | CH3 | CF3 | H | Cl | CH3 |
A-1524 | CF3 | CF3 | H | Cl | CH3 |
A-1525 | OCH3 | CF3 | H | Cl | CH3 |
A-1526 | F | H | F | Cl | CH3 |
A-1527 | Cl | H | F | Cl | CH3 |
A-1528 | CH3 | H | F | Cl | CH3 |
A-1529 | CF3 | H | F | Cl | CH3 |
A-1530 | OCH3 | H | F | Cl | CH3 |
A-1531 | F | F | F | Cl | CH3 |
A-1532 | Cl | F | F | Cl | CH3 |
A-1533 | CH3 | F | F | Cl | CH3 |
A-1534 | CF3 | F | F | Cl | CH3 |
A-1535 | OCH3 | F | F | Cl | CH3 |
A-1536 | F | Cl | F | Cl | CH3 |
A-1537 | Cl | Cl | F | Cl | CH3 |
A-1538 | CH3 | Cl | F | C | CH3 |
A-1539 | CF3 | Cl | F | Cl | CH3 |
A-1540 | OCH3 | Cl | F | Cl | CH3 |
A-1541 | F | CH3 | F | Cl | CH3 |
A-1542 | Cl | CH3 | F | Cl | CH3 |
A-1543 | CH3 | CH3 | F | Cl | CH3 |
A-1544 | CF3 | CH3 | F | Cl | CH3 |
A-1545 | OCH3 | CH3 | F | Cl | CH3 |
A-1546 | F | CF3 | F | Cl | CH3 |
A-1547 | Cl | CF3 | F | Cl | CH3 |
A-1548 | CH3 | CF3 | F | Cl | CH3 |
A-1549 | CF3 | CF3 | F | Cl | CH3 |
A-1550 | OCH3 | CF3 | F | Cl | CH3 |
A-1551 | F | H | Cl | Cl | CH3 |
A-1552 | Cl | H | Cl | Cl | CH3 |
A-1553 | CH3 | H | Cl | Cl | CH3 |
A-1554 | CF3 | H | Cl | Cl | CH3 |
A-1555 | OCH3 | H | Cl | Cl | CH3 |
A-1556 | F | F | Cl | Cl | CH3 |
A-1557 | Cl | F | Cl | Cl | CH3 |
A-1558 | CH3 | F | Cl | Cl | CH3 |
A-1559 | CF3 | F | Cl | Cl | CH3 |
A-1560 | OCH3 | F | Cl | Cl | CH3 |
A-1561 | F | Cl | Cl | Cl | CH3 |
A-1562 | Cl | Cl | Cl | Cl | CH3 |
A-1563 | CH3 | Cl | Cl | Cl | CH3 |
A-1564 | CF3 | Cl | Cl | Cl | CH3 |
A-1565 | OCH3 | Cl | Cl | Cl | CH3 |
A-1566 | F | CH3 | Cl | Cl | CH3 |
A-1567 | Cl | CH3 | Cl | Cl | CH3 |
A-1568 | CH3 | CH3 | Cl | Cl | CH3 |
A-1569 | CF3 | CH3 | Cl | Cl | CH3 |
A-1570 | OCH3 | CH3 | Cl | Cl | CH3 |
A-1571 | F | CF3 | Cl | Cl | CH3 |
A-1572 | Cl | CF3 | Cl | Cl | CH3 |
A-1573 | CH3 | CF3 | Cl | Cl | CH3 |
A-1574 | CF3 | CF3 | Cl | Cl | CH3 |
A-1575 | OCH3 | CF3 | Cl | Cl | CH3 |
A-1576 | F | H | CH3 | Cl | CH3 |
A-1577 | Cl | H | CH3 | Cl | CH3 |
A-1578 | CH3 | H | CH3 | Cl | CH3 |
A-1579 | CF3 | H | CH3 | Cl | CH3 |
A-1580 | OCH3 | H | CH3 | Cl | CH3 |
A-1581 | F | F | CH3 | Cl | CH3 |
A-1582 | Cl | F | CH3 | Cl | CH3 |
A-1583 | CH3 | F | CH3 | Cl | CH3 |
A-1584 | CF3 | F | CH3 | Cl | CH3 |
A-1585 | OCH3 | F | CH3 | Cl | CH3 |
A-1586 | F | C | CH3 | Cl | CH3 |
A-1587 | Cl | Cl | CH3 | Cl | CH3 |
A-1588 | CH3 | Cl | CH3 | Cl | CH3 |
A-1589 | CF3 | Cl | CH3 | Cl | CH3 |
A-1590 | OCH3 | Cl | CH3 | Cl | CH3 |
A-1591 | F | CH3 | CH3 | Cl | CH3 |
A-1592 | Cl | CH3 | CH3 | Cl | CH3 |
A-1593 | CH3 | CH3 | CH3 | Cl | CH3 |
A-1594 | CF3 | CH3 | CH3 | Cl | CH3 |
A-1595 | OCH3 | CH3 | CH3 | Cl | CH3 |
A-1596 | F | CF3 | CH3 | Cl | CH3 |
A-1597 | Cl | CF3 | CH3 | Cl | CH3 |
A-1598 | CH3 | CF3 | CH3 | Cl | CH3 |
A-1599 | CF3 | CF3 | CH3 | Cl | CH3 |
A-1600 | OCH3 | CF3 | CH3 | Cl | CH3 |
A-1601 | F | H | CF3 | Cl | CH3 |
A-1602 | Cl | H | CF3 | Cl | CH3 |
A-1603 | CH3 | H | CF3 | Cl | CH3 |
A-1604 | CF3 | H | CF3 | Cl | CH3 |
A-1605 | OCH3 | H | CF3 | Cl | CH3 |
A-1606 | F | F | CF3 | Cl | CH3 |
A-1607 | Cl | F | CF3 | Cl | CH3 |
A-1608 | CH3 | F | CF3 | Cl | CH3 |
A-1609 | CF3 | F | CF3 | Cl | CH3 |
A-1610 | OCH3 | F | CF3 | Cl | CH3 |
A-1611 | F | Cl | CF3 | Cl | CH3 |
A-1612 | Cl | Cl | CF3 | Cl | CH3 |
A-1613 | CH3 | Cl | CF3 | Cl | CH3 |
A-1614 | CF3 | Cl | CF3 | Cl | CH3 |
A-1615 | OCH3 | Cl | CF3 | Cl | CH3 |
A-1616 | F | CH3 | CF3 | Cl | CH3 |
A-1617 | Cl | CH3 | CF3 | Cl | CH3 |
A-1618 | CH3 | CH3 | CF3 | Cl | CH3 |
A-1619 | CF3 | CH3 | CF3 | Cl | CH3 |
A-1620 | OCH3 | CH3 | CF3 | Cl | CH3 |
A-1621 | F | CF3 | CF3 | Cl | CH3 |
A-1622 | Cl | CF3 | CF3 | Cl | CH3 |
A-1623 | CH3 | CF3 | CF3 | Cl | CH3 |
A-1624 | CF3 | CF3 | CF3 | Cl | CH3 |
A-1625 | OCH3 | CF3 | CF3 | Cl | CH3 |
A-1626 | F | H | H | CH3 | CH3 |
A-1627 | Cl | H | H | CH3 | CH3 |
A-1628 | CH3 | H | H | CH3 | CH3 |
A-1629 | CF3 | H | H | CH3 | CH3 |
A-1630 | OCH3 | H | H | CH3 | CH3 |
A-1631 | F | F | H | CH3 | CH3 |
A-1632 | Cl | F | H | CH3 | CH3 |
A-1633 | CH3 | F | H | CH3 | CH3 |
A-1634 | CF3 | F | H | CH3 | CH3 |
A-1635 | OCH3 | F | H | CH3 | CH3 |
A-1636 | F | Cl | H | CH3 | CH3 |
A-1637 | Cl | Cl | H | CH3 | CH3 |
A-1638 | CF3 | Cl | H | CH3 | CH3 |
A-1639 | CF3 | Cl | H | CH3 | CH3 |
A-1640 | OCH3 | Cl | H | CH3 | CH3 |
A-1641 | F | CH3 | H | CH3 | CH3 |
A-1642 | Cl | CH3 | H | CH3 | CH3 |
A-1643 | CH3 | CH3 | H | CH3 | CH3 |
A-1644 | CF3 | CH3 | H | CH3 | CH3 |
A-1645 | OCH3 | CH3 | H | CH3 | CH3 |
A-1646 | F | CF3 | H | CH3 | CH3 |
A-1647 | Cl | CF3 | H | CH3 | CH3 |
A-1648 | CH3 | CF3 | H | CH3 | CH3 |
A-1649 | CF3 | CF3 | H | CH3 | CH3 |
A-1650 | OCH3 | CF3 | H | CH3 | CH3 |
A-1651 | F | H | F | CH3 | CH3 |
A-1652 | Cl | H | F | CH3 | CH3 |
A-1653 | CH3 | H | F | CH3 | CH3 |
A-1654 | CF3 | H | F | CH3 | CH3 |
A-1655 | OCH3 | H | F | CH3 | CH3 |
A-1656 | F | F | F | CH3 | CH3 |
A-1657 | Cl | F | F | CH3 | CH3 |
A-1658 | CH3 | F | F | CH3 | CH3 |
A-1659 | CF3 | F | F | CH3 | CH3 |
A-1660 | OCH3 | F | F | CH3 | CH3 |
A-1661 | F | Cl | F | CH3 | CH3 |
A-1662 | Cl | Cl | F | CH3 | CH3 |
A-1663 | CH3 | Cl | F | CH3 | CH3 |
A-1664 | CF3 | Cl | F | CH3 | CH3 |
A-1665 | OCH3 | Cl | F | CH3 | CH3 |
A-1666 | F | CH3 | F | CH3 | CH3 |
A-1667 | Cl | CH3 | F | CH3 | CH3 |
A-1668 | CH3 | CH3 | F | CH3 | CH3 |
A-1669 | CF3 | CH3 | F | CH3 | CH3 |
A-1670 | OCH3 | CH3 | F | CH3 | CH3 |
A-1671 | F | CF3 | F | CH3 | CH3 |
A-1672 | Cl | CF3 | F | CH3 | CH3 |
A-1673 | CH3 | CF3 | F | CH3 | CH3 |
A-1674 | CF3 | CF3 | F | CH3 | CH3 |
A-1675 | OCH3 | CF3 | F | CH3 | CH3 |
A-1676 | F | H | Cl | CH3 | CH3 |
A-1677 | Cl | H | Cl | CH3 | CH3 |
A-1678 | CH3 | H | Cl | CH3 | CH3 |
A-H679 | CF3 | H | Cl | CH3 | CH3 |
A-1680 | OCH3 | H | Cl | CH3 | CH3 |
A-1681 | F | F | Cl | CH3 | CH3 |
A-1682 | Cl | F | Cl | CH3 | CH3 |
A-1683 | CH3 | F | Cl | CH3 | CH3 |
A-1684 | CF3 | F | Cl | CH3 | CH3 |
A-1685 | OCH3 | F | Cl | CH3 | CH3 |
A-1686 | F | Cl | Cl | CH3 | CH3 |
A-1687 | Cl | Cl | Cl | CH3 | CH3 |
A-1688 | CH3 | Cl | Cl | CH3 | CH3 |
A-1689 | CF3 | Cl | Cl | CH3 | CH3 |
A-1690 | OCH3 | Cl | Cl | CH3 | CH3 |
A-1691 | F | CH3 | Cl | CH3 | CH3 |
A-1692 | Cl | CH3 | Cl | CH3 | CH3 |
A-1693 | CH3 | CH3 | Cl | CH3 | CH3 |
A-1694 | CF3 | CH3 | Cl | CH3 | CH3 |
A-1695 | OCH3 | CH3 | Cl | CH3 | CH3 |
A-1696 | F | CF3 | Cl | CH3 | CH3 |
A-1697 | Cl | CF3 | Cl | CH3 | CH3 |
A-1698 | CH3 | CF3 | Cl | CH3 | CH3 |
A-1699 | CF3 | CF3 | Cl | CH3 | CH3 |
A-1700 | OCH3 | CF3 | Cl | CH3 | CH3 |
A-1701 | F | H | CH3 | CH3 | CH3 |
A-1702 | Cl | H | CH3 | CH3 | CH3 |
A-1703 | CH3 | H | CH3 | CH3 | CH3 |
A-1704 | CF3 | H | CH3 | CH3 | CH3 |
A-1705 | OCH3 | H | CH3 | CH3 | CH3 |
A-1706 | F | F | CH3 | CH3 | CH3 |
A-1707 | Cl | F | CH3 | CH3 | CH3 |
A-1708 | CH3 | F | CH3 | CH3 | CH3 |
A-1709 | CF3 | F | CH3 | CH3 | CH3 |
A-1710 | OCH3 | F | CH3 | CH3 | CH3 |
A-1711 | F | Cl | CH3 | CH3 | CH3 |
A-1712 | Cl | Cl | CH3 | CH3 | CH3 |
A-1713 | CH3 | Cl | CH3 | CH3 | CH3 |
A-1714 | CF3 | Cl | CH3 | CH3 | CH3 |
A-1715 | OCH3 | Cl | CH3 | CH3 | CH3 |
A-1716 | F | CH3 | CH3 | CH3 | CH3 |
A-1717 | Cl | CH3 | CH3 | CH3 | CH3 |
A-1718 | CH3 | CH3 | CH3 | CH3 | CH3 |
A-1719 | CF3 | CH3 | CH3 | CH3 | CH3 |
A-1720 | OCH3 | CH3 | CH3 | CH3 | CH3 |
A-1721 | F | CF3 | CH3 | CH3 | CH3 |
A-1722 | Cl | CF3 | CH3 | CH3 | CH3 |
A-1723 | CH3 | CF3 | CH3 | CH3 | CHH3 |
A-1724 | CF3 | CF3 | CH3 | CH3 | CH3 |
A-1725 | OCH3 | CF3 | CH3 | CH3 | CH3 |
A-1726 | F | H | CF3 | CH3 | CH3 |
A-1727 | Cl | H | CF3 | CH3 | CH3 |
A-1728 | CH3 | H | CF3 | CH3 | CH3 |
A-1729 | CF3 | H | CF3 | CH3 | CH3 |
A-1730 | OCH3 | H | CF3 | CH3 | CH3 |
A-1731 | F | F | CF3 | CH3 | CH3 |
A-1732 | Cl | F | CF3 | CH3 | CH3 |
A-1733 | CH3 | F | CF3 | CH3 | CH3 |
A-1734 | CF3 | F | CF3 | CH3 | CH3 |
A-1735 | OCH3 | F | CF3 | CH3 | CH3 |
A-1736 | F | Cl | CF3 | CH3 | CH3 |
A-1737 | Cl | Cl | CF3 | CH3 | CH3 |
A-1738 | CH3 | Cl | CF3 | CH3 | CH3 |
A-1739 | CF3 | Cl | CF3 | CH3 | CH3 |
A-1740 | OCH3 | Cl | CF3 | CH3 | CH3 |
A-1741 | F | CH3 | CF3 | CH3 | CH3 |
A-1742 | Cl | CH3 | CF3 | CH3 | CH3 |
A-1743 | CH3 | CH3 | CF3 | CH3 | CH3 |
A-1744 | CF3 | CH3 | CF3 | CH3 | CH3 |
A-1745 | OCH3 | CH3 | CF3 | CH3 | CH3 |
A-1746 | F | CF3 | CF3 | CH3 | CH3 |
A-1747 | Cl | CF3 | CF3 | CH3 | CH3 |
A-1748 | CH3 | CF3 | CF3 | CH3 | CH3 |
A-1749 | CF3 | CF3 | CF3 | CH3 | CH3 |
A-1750 | OCH3 | CF3 | CF3 | CH3 | CH3 |
A-1751 | F | H | H | CF3 | CH3 |
A-1752 | Cl | H | H | CF3 | CH3 |
A-1753 | CH3 | H | H | CF3 | CH3 |
A-1754 | CF3 | H | H | CF3 | CH3 |
A-1755 | OCH3 | H | H | CF3 | CH3 |
A-1756 | F | F | H | CF3 | CH3 |
A-1757 | Cl | F | H | CF3 | CH3 |
A-1758 | CH3 | F | H | CF3 | CH3 |
A-1759 | CF3 | F | H | CF3 | CH3 |
A-1760 | OCH3 | F | H | CF3 | CH3 |
A-1761 | F | Cl | H | CF3 | CH3 |
A-1762 | Cl | Cl | H | CF3 | CH3 |
A-1763 | CH3 | Cl | H | CF3 | CH3 |
A-1764 | CF3 | Cl | H | CF3 | CH3 |
A-1765 | OCH3 | Cl | H | CF3 | CH3 |
A-1766 | F | CH3 | H | CF3 | CH3 |
A-1767 | Cl | CH3 | H | CF3 | CH3 |
A-1768 | CH3 | CH3 | H | CF3 | CH3 |
A-1769 | CF3 | CH3 | H | CF3 | CH3 |
A-1770 | OCH3 | CH3 | H | CF3 | CH3 |
A-1771 | F | CF3 | H | CF3 | CH3 |
A-1772 | Cl | CF3 | H | CF3 | CH3 |
A-1773 | CH3 | CF3 | H | CF3 | CH3 |
A-1774 | CF3 | CF3 | H | CF3 | CH3 |
A-1775 | OCH3 | CF3 | H | CF3 | CH3 |
A-1776 | F | H | F | CF3 | CH3 |
A-1777 | Cl | H | F | CF3 | CH3 |
A-1778 | CH3 | H | F | CF3 | CH3 |
A-1779 | CF3 | H | F | CF3 | CH3 |
A-1780 | OCH3 | H | F | CF3 | CH3 |
A-1781 | F | F | F | CF3 | CH3 |
A-1782 | Cl | F | F | CF3 | CH3 |
A-1783 | CH3 | F | F | CF3 | CH3 |
A-1784 | CF3 | F | F | CF3 | CH3 |
A-1785 | OCH3 | F | F | CF3 | CH3 |
A-1786 | F | Cl | F | CF3 | CH3 |
A-1787 | Cl | Cl | F | CF3 | CH3 |
A-1788 | CH3 | Cl | F | CF3 | CH3 |
A-1789 | CF3 | Cl | F | CF3 | CH3 |
A-1790 | OCH3 | Cl | F | CF3 | CH3 |
A-1791 | F | CH3 | F | CF3 | CH3 |
A-1792 | Cl | CH3 | F | CF3 | CH3 |
A-1793 | CH3 | CH3 | F | CF3 | CH3 |
A-1794 | CF3 | CH3 | F | CF3 | CH3 |
A-1795 | OCH3 | CH3 | F | CF3 | CH3 |
A-1796 | F | CF3 | F | CF3 | CH3 |
A-1797 | Cl | CF3 | F | CF3 | CH3 |
A-1798 | CH3 | CF3 | F | CF3 | CH3 |
A-1799 | CF3 | CF3 | F | CF3 | CH3 |
A-1800 | OCH3 | CF3 | F | CF3 | CH3 |
A-1801 | F | H | Cl | CF3 | CH3 |
A-1802 | Cl | H | Cl | CF3 | CH3 |
A-1803 | CH3 | H | Cl | CF3 | CH3 |
A-1804 | CF3 | H | Cl | CF3 | CH3 |
A-1805 | OCH3 | H | Cl | CF3 | CH3 |
A-1806 | F | F | Cl | CF3 | CH3 |
A-1807 | Cl | F | Cl | CF3 | CH3 |
A-1808 | CH3 | F | Cl | CF3 | CH3 |
A-1809 | CF3 | F | Cl | CF3 | CH3 |
A-1810 | OCH3 | F | Cl | CF3 | CH3 |
A-1811 | F | Cl | Cl | CF3 | CH3 |
A-1812 | Cl | Cl | Cl | CF3 | CH3 |
A-1813 | CH3 | Cl | Cl | CF3 | CH3 |
A-1814 | CF3 | Cl | Cl | CF3 | CH3 |
A-1815 | OCH3 | Cl | Cl | CF3 | CH3 |
A-1816 | F | CH3 | Cl | CF3 | CH3 |
A-1817 | Cl | CH3 | Cl | CF3 | CH3 |
A-1818 | CH3 | CH3 | Cl | CF3 | CH3 |
A-1819 | CF3 | CH3 | Cl | CF3 | CH3 |
A-1820 | OCH3 | CH3 | Cl | CF3 | CH3 |
A-1821 | F | CF3 | Cl | CF3 | CH3 |
A-1822 | Cl | CF3 | Cl | CF3 | CH3 |
A-1823 | CH3 | CF3 | C | CF3 | CH3 |
A-1824 | CF3 | CF3 | Cl | CF3 | CH3 |
A-1825 | OCH3 | CF3 | Cl | CF3 | CH3 |
A-1826 | F | H | CH3 | CF3 | CH3 |
A-1827 | Cl | H | CH3 | CF3 | CH2 |
A-1828 | CH3 | H | CH3 | CF3 | CH3 |
A-1829 | CF3 | H | CH3 | CF3 | CH3 |
A-1830 | OCH3 | H | CH3 | CF3 | CH3 |
A-1831 | F | F | CH3 | CF3 | CH3 |
A-1832 | Cl | F | CH3 | CF3 | CH3 |
A-1833 | CH3 | F | CH3 | CF3 | CH3 |
A-1834 | CF3 | F | CH3 | CF3 | CH3 |
A-1835 | OCH3 | F | CH3 | CF3 | CH3 |
A-1836 | F | Cl | CH3 | CF3 | CH3 |
A-1837 | Cl | Cl | CH3 | CF3 | CH3 |
A-1838 | CH3 | Cl | CH3 | CF3 | CH3 |
A-1839 | CF3 | Cl | CH3 | CF3 | CH3 |
A-1840 | OCH3 | Cl | CH3 | CF3 | CH3 |
A-1841 | F | CH3 | CH3 | CF3 | CH3 |
A-1842 | Cl | CH3 | CH3 | CF3 | CH3 |
A-1843 | CH3 | CH3 | CH3 | CF3 | CH3 |
A-1844 | CF3 | CH3 | CH3 | CF3 | CH3 |
A-1845 | OCH3 | CH3 | CH3 | CF3 | CH3 |
A-1846 | F | CF3 | CH3 | CF3 | CH3 |
A-1847 | Cl | CF3 | CH3 | CF3 | CH3 |
A-1848 | CH3 | CF3 | CH3 | CF3 | CH3 |
A-1849 | CF3 | CF3 | CH3 | CF3 | CH3 |
A-1850 | OCH3 | CF3 | CH3 | CF3 | CH3 |
A-1851 | F | H | CF3 | CF3 | CH3 |
A-1852 | Cl | H | CF3 | CF3 | CH3 |
A-1853 | CH3 | H | CF3 | CF3 | CH3 |
A-1854 | CF3 | H | CF3 | CF3 | CH3 |
A-1855 | OCH3 | H | CF3 | CF3 | CH3 |
A-1856 | F | F | CF3 | CF3 | CH3 |
A-1857 | Cl | F | CF3 | CF3 | CH3 |
A-1858 | CH3 | F | CF2 | CF3 | CH3 |
A-1859 | CF3 | F | CF3 | CF3 | CH3 |
A-1860 | OCH3 | F | CF3 | CF3 | CH3 |
A-1861 | F | Cl | CF3 | CF3 | CH3 |
A-1862 | Cl | Cl | CF3 | CF3 | CH3 |
A-1863 | CH3 | Cl | CF3 | CF3 | CH3 |
A-1864 | CF3 | Cl | CF3 | CF3 | CH3 |
A-1865 | OCH3 | Cl | CF3 | CF3 | CH3 |
A-1866 | F | CH3 | CF3 | CF3 | CH3 |
A-1867 | Cl | CH3 | CF3 | CF3 | CH3 |
A-1868 | CH3 | CH3 | CF3 | CF3 | CH3 |
A-1869 | CF3 | CH3 | CF3 | CF3 | CH3 |
A-1870 | OCH3 | CH3 | CF3 | CF3 | CH3 |
A-1871 | F | CF3 | CF3 | CF3 | CH3 |
A-1872 | Cl | CF3 | CF3 | CF3 | CH3 |
A-1873 | CH3 | CF3 | CF3 | CF3 | CH3 |
A-1874 | CF3 | CF3 | CF3 | CF3 | CH3 |
A-1875 | OCH3 | CF3 | CF3 | CF3 | CH3 |
A-1876 | F | H | H | H | CF3 |
A-1877 | Cl | H | H | H | CF3 |
A-1878 | CH3 | H | H | H | CF3 |
A-1879 | CF3 | H | H | H | CF3 |
A-1880 | OCH3 | H | H | H | CF3 |
A-1881 | F | F | H | H | CF3 |
A-1882 | Cl | F | H | H | CF3 |
A-1883 | CH3 | F | H | H | CF3 |
A-1884 | CF3 | F | H | H | CF3 |
A-1885 | OCH3 | F | H | H | CF3 |
A-1886 | F | Cl | H | H | CF3 |
A-1887 | Cl | Cl | H | H | CF3 |
A-1888 | CH3 | Cl | H | H | CF3 |
A-1889 | CF3 | Cl | H | H | CF3 |
A-1890 | OCH3 | Cl | H | H | CF3 |
A-1891 | F | CH3 | H | H | CF3 |
A-1892 | Cl | CH3 | H | H | CF3 |
A-1893 | CH3 | CH3 | H | H | CF3 |
A-1894 | CF3 | CH3 | H | H | CF3 |
A-1895 | OCH3 | CH3 | H | H | CF3 |
A-1896 | F | CF3 | H | H | CF3 |
A-1897 | Cl | CF3 | H | H | CF3 |
A-1898 | CH3 | CF3 | H | H | CF3 |
A-1899 | CF3 | CF3 | H | H | CF3 |
A-1900 | OCH3 | CF3 | H | H | CF3 |
A-1901 | F | H | F | H | CF3 |
A-1902 | Cl | H | F | H | CF3 |
A-1903 | CH3 | H | F | H | CF3 |
A-1904 | CF3 | H | F | H | CF3 |
A-1905 | OCH3 | H | F | H | CF3 |
A-1906 | F | F | F | H | CF3 |
A-1907 | Cl | F | F | H | CF3 |
A-1908 | CH3 | F | F | H | CF3 |
A-1909 | CF3 | F | F | H | CF3 |
A-1910 | OCH3 | F | F | H | CF3 |
A-1911 | F | Cl | F | H | CF3 |
A-1912 | Cl | Cl | F | H | CF3 |
A-1913 | CH3 | Cl | F | H | CF3 |
A-1914 | CF3 | Cl | F | H | CF3 |
A-1915 | OCH3 | Cl | F | H | CF3 |
A-1916 | F | CH3 | F | H | CF3 |
A-1917 | Cl | CH3 | F | H | CF3 |
A-1918 | CH3 | CH3 | F | H | CF3 |
A-1919 | CF3 | CH3 | F | H | CF3 |
A-1920 | OCH3 | CH3 | F | H | CF3 |
A-1921 | F | CF3 | F | H | CF3 |
A-1922 | Cl | CF3 | F | H | CF3 |
A-1923 | CH3 | CF3 | F | H | CF3 |
A-1924 | CF3 | CF3 | F | H | CF3 |
A-1925 | OCH3 | CF3 | F | H | CF3 |
A-1926 | F | H | Cl | H | CF3 |
A-1927 | Cl | H | Cl | H | CF3 |
A-1928 | CH3 | H | Cl | H | CF3 |
A-1929 | CF3 | H | Cl | H | CF3 |
A-1930 | OCH3 | H | Cl | H | CF3 |
A-1931 | F | F | Cl | H | CF3 |
A-1932 | Cl | F | Cl | H | CF3 |
A-1933 | CH3 | F | Cl | H | CF3 |
A-1934 | CF3 | F | Cl | H | CF3 |
A-1935 | OCH3 | F | Cl | H | CF3 |
A-1936 | F | Cl | Cl | H | CF3 |
A-1937 | Cl | Cl | Cl | H | CF3 |
A-1938 | CH3 | Cl | Cl | H | CF3 |
A-1939 | CF3 | Cl | Cl | H | CF3 |
A-1940 | OCH3 | Cl | Cl | H | CF3 |
A-1941 | F | CH3 | Cl | H | CF3 |
A-1942 | Cl | CH3 | Cl | H | CF3 |
A-1943 | CH3 | CH3 | Cl | H | CF3 |
A-1944 | CF3 | CH3 | Cl | H | CF3 |
A-1945 | OCH3 | CH3 | Cl | H | CF3 |
A-1946 | F | CF3 | Cl | H | CF3 |
A-1947 | Cl | CF3 | Cl | H | CF3 |
A-1948 | CH3 | CF3 | Cl | H | CF3 |
A-1949 | CF3 | CF3 | Cl | H | CF3 |
A-1950 | OCH3 | CF3 | Cl | H | CF3 |
A-1951 | F | H | CH3 | H | CF3 |
A-1952 | Cl | H | CH3 | H | CF3 |
A-1953 | CH3 | H | CH3 | H | CF3 |
A-1954 | CF3 | H | CH3 | H | CF3 |
A-1955 | OCH3 | H | CH3 | H | CF3 |
A-1956 | F | F | CH3 | H | CF3 |
A-1957 | Cl | F | CH3 | H | CF3 |
A-1958 | CH3 | F | CH3 | H | CF3 |
A-1959 | CF3 | F | CH3 | H | CF3 |
A-1960 | OCH3 | F | CH3 | H | CF3 |
A-1961 | F | Cl | CH3 | H | CF3 |
A-1962 | Cl | Cl | CH3 | H | CF3 |
A-1963 | CH3 | Cl | CH3 | H | CF3 |
A-1964 | CF3 | Cl | CH3 | H | CF3 |
A-1965 | OCH3 | Cl | CH3 | H | CF3 |
A-1966 | F | CH3 | CH3 | H | CF3 |
A-1967 | Cl | CH3 | CH3 | H | CF3 |
A-1968 | CH3 | CH3 | CH3 | H | CF3 |
A-1969 | CF3 | CH3 | CH3 | H | CF3 |
A-1970 | OCH3 | CH3 | CH3 | H | CF3 |
A-1971 | F | CF3 | CH3 | H | CF3 |
A-1972 | Cl | CF3 | CH3 | H | CF3 |
A-1973 | CH3 | CF3 | CH3 | H | CF3 |
A-1974 | CF3 | CF3 | CH3 | H | CF3 |
A-1975 | OCH3 | CF3 | CH3 | H | CF3 |
A-1976 | F | H | CF3 | H | CF3 |
A-1977 | Cl | H | CF3 | H | CF3 |
A-1978 | CH3 | H | CF3 | H | CF3 |
A-1979 | CF3 | H | CF3 | H | CF3 |
A-1980 | OCH3 | H | CF3 | H | CF3 |
A-1981 | F | F | CF3 | H | CF3 |
A-1982 | Cl | F | CF3 | H | CF3 |
A-1983 | CH3 | F | CF3 | H | CF3 |
A-1984 | CF3 | F | CF3 | H | CF3 |
A-1985 | OCH3 | F | CF3 | H | CF3 |
A-1986 | F | Cl | CF3 | H | CF3 |
A-1987 | Cl | Cl | CF3 | H | CF3 |
A-1988 | CH3 | Cl | CF3 | H | CF3 |
A-1989 | CF3 | Cl | CF3 | H | CF3 |
A-1990 | OCH3 | Cl | CF3 | H | CF3 |
A-1991 | F | CH3 | CF3 | H | CF3 |
A-1992 | Cl | CH3 | CF3 | H | CF3 |
A-1993 | CH3 | CH3 | CF3 | H | CF3 |
A-1994 | CF3 | CH3 | CF3 | H | CF3 |
A-1995 | OCH3 | CH3 | CF3 | H | CF3 |
A-1996 | F | CF3 | CF3 | H | CF3 |
A-1997 | Cl | CF3 | CF3 | H | CF3 |
A-1998 | CH3 | CF3 | CF3 | H | CF3 |
A-1999 | CF3 | CF3 | CF3 | H | CF3 |
A-2000 | OCH3 | CF3 | CF3 | H | CF3 |
A-2001 | F | H | H | F | CF3 |
A-2002 | Cl | H | H | F | CF3 |
A-2003 | CH3 | H | H | F | CF3 |
A-2004 | CF3 | H | H | F | CF3 |
A-2005 | OCH3 | H | H | F | CF3 |
A-2006 | F | F | H | F | CF3 |
A-2007 | Cl | F | H | F | CF3 |
A-2008 | CH3 | F | H | F | CF3 |
A-2009 | CF3 | F | H | F | CF3 |
A-2010 | OCH3 | F | H | F | CF3 |
A-2011 | F | Cl | H | F | CF3 |
A-2012 | Cl | Cl | H | F | CF3 |
A-2013 | CH3 | Cl | H | F | CF3 |
A-2014 | CF3 | Cl | H | F | CF3 |
A-2015 | OCH3 | Cl | H | F | CF3 |
A-2016 | F | CH3 | H | F | CF3 |
A-2017 | Cl | CH3 | H | F | CF3 |
A-2018 | CH3 | CH3 | H | F | CF3 |
A-2019 | CF3 | CH3 | H | F | CF3 |
A-2020 | OCH3 | CH3 | H | F | CF3 |
A-2021 | F | CF3 | H | F | CF3 |
A-2022 | Cl | CF3 | H | F | CF3 |
A-2023 | CH3 | CF3 | H | F | CF3 |
A-2024 | CF3 | CF3 | H | F | CF3 |
A-2025 | OCH3 | CF3 | H | F | CF3 |
A-2026 | F | H | F | F | CF3 |
A-2027 | Cl | H | F | F | CF3 |
A-2028 | CH3 | H | F | F | CF3 |
A-2029 | CF3 | H | F | F | CF3 |
A-2030 | OCH3 | H | F | F | CF3 |
A-2031 | F | F | F | F | CF3 |
A-2032 | Cl | F | F | F | CF3 |
A-2033 | CH3 | F | F | F | CF3 |
A-2034 | CF3 | F | F | F | CF3 |
A-2035 | OCH3 | F | F | F | CF3 |
A-2036 | F | Cl | F | F | CF3 |
A-2037 | Cl | Cl | F | F | CF3 |
A-2038 | CH3 | Cl | F | F | CF3 |
A-2039 | CF3 | Cl | F | F | CF3 |
A-2040 | OCH3 | Cl | F | F | CF3 |
A-2041 | F | CH3 | F | F | CF3 |
A-2042 | Cl | CH3 | F | F | CF3 |
A-2043 | CH3 | CH3 | F | F | CF3 |
A-2044 | CF3 | CH3 | F | F | CF3 |
A-2045 | OCH3 | CH3 | F | F | CF3 |
A-2046 | F | CF3 | F | F | CF3 |
A-2047 | Cl | CF3 | F | F | CF3 |
A-2048 | CH3 | CF3 | F | F | CF3 |
A-2049 | CF3 | CF3 | F | F | CF3 |
A-2050 | OCH3 | CF3 | F | F | CF3 |
A-2051 | F | H | Cl | F | CF3 |
A-2052 | Cl | H | Cl | F | CF3 |
A-2053 | CH3 | H | Cl | F | CF3 |
A-2054 | CF3 | H | Cl | F | CF3 |
A-2055 | OCH3 | H | Cl | F | CF3 |
A-2056 | F | F | Cl | F | CF3 |
A-2057 | Cl | F | Cl | F | CF3 |
A-2058 | CH3 | F | Cl | F | CF3 |
A-2059 | CF3 | F | Cl | F | CF3 |
A-2060 | OCH3 | F | Cl | F | CF3 |
A-2061 | F | Cl | Cl | F | CF3 |
A-2062 | Cl | Cl | Cl | F | CF3 |
A-2063 | CH3 | Cl | Cl | F | CF3 |
A-2064 | CF3 | Cl | Cl | F | CF3 |
A-2065 | OCH3 | Cl | Cl | F | CF3 |
A-2066 | F | CH3 | Cl | F | CF3 |
A-2067 | Cl | CH3 | Cl | F | CF3 |
A-2068 | CH3 | CH3 | Cl | F | CF3 |
A-2069 | CF3 | CH3 | Cl | F | CF3 |
A-2070 | OCH3 | CH3 | Cl | F | CF3 |
A-2071 | F | CH3 | Cl | F | CF3 |
A-2072 | Cl | CF3 | Cl | F | CF3 |
A-2073 | CH3 | CF3 | Cl | F | CF3 |
A-2074 | CF3 | CF3 | Cl | F | CF3 |
A-2075 | OCH3 | CF3 | Cl | F | CF3 |
A-2076 | F | H | CH3 | F | CF3 |
A-2077 | Cl | H | CH3 | F | CF3 |
A-2078 | CH3 | H | CH3 | F | CF3 |
A-2079 | CF3 | H | CH3 | F | CF3 |
A-2080 | OCH3 | H | CH3 | F | CF3 |
A-2081 | F | F | CH3 | F | CF3 |
A-2082 | Cl | F | CH3 | F | CF3 |
A-2083 | CH3 | F | CH3 | F | CF3 |
A-2084 | CF3 | F | CH3 | F | CF3 |
A-2085 | OCH3 | F | CH3 | F | CF3 |
A-2086 | F | Cl | CH3 | F | CF3 |
A-2087 | Cl | Cl | CH3 | F | CF3 |
A-2088 | CH3 | Cl | CH3 | F | CF3 |
A-2089 | CF3 | Cl | CH3 | F | CF3 |
A-2090 | OCH3 | Cl | CH3 | F | CF3 |
A-2091 | F | CH3 | CH3 | F | CF3 |
A-2092 | Cl | CH3 | CH3 | F | CF3 |
A-2093 | CH3 | CH3 | CH3 | F | CF3 |
A-2094 | CF3 | CH3 | CH3 | F | CF3 |
A-2095 | OCH3 | CH3 | CH3 | F | CF3 |
A-2096 | F | CF3 | CH3 | F | CF3 |
A-2097 | Cl | CF3 | CH3 | F | CF3 |
A-2098 | CH3 | CF3 | CH3 | F | CF3 |
A-2099 | CF3 | CF3 | CH3 | F | CF3 |
A-2100 | OCH3 | CF3 | CH3 | F | CF3 |
A-2101 | F | H | CF3 | F | CF3 |
A-2102 | Cl | H | CF3 | F | CF3 |
A-2103 | CH3 | H | CF3 | F | CF3 |
A-2104 | CF3 | H | CF3 | F | CF3 |
A-2105 | OCH3 | H | CF3 | F | CF3 |
A-2106 | F | F | CF3 | F | CF3 |
A-2107 | Cl | F | CF3 | F | CF3 |
A-2108 | CH3 | F | CF3 | F | CF3 |
A-2109 | CF3 | F | CF3 | F | CF3 |
A-2110 | OCH3 | F | CF3 | F | CF3 |
A-2111 | F | Cl | CF3 | F | CF3 |
A-2112 | Cl | Cl | CF3 | F | CF3 |
A-2113 | CH3 | Cl | CF3 | F | CF3 |
A-2114 | CF3 | Cl | CF3 | F | CF3 |
A-2115 | OCH3 | Cl | CF3 | F | CF3 |
A-2116 | F | CH3 | CF3 | F | CF3 |
A-2117 | Cl | CH3 | CF3 | F | CF3 |
A-2118 | CH3 | CH3 | CF3 | F | CF3 |
A-2119 | CF3 | CH3 | CF3 | F | CF3 |
A-2120 | OCH3 | CH3 | CF3 | F | CF3 |
A-2121 | F | CF3 | CF3 | F | CF3 |
A-2122 | Cl | CF3 | CF3 | F | CF3 |
A-2123 | CH3 | CF3 | CF3 | F | CF3 |
A-2124 | CF3 | CF3 | CF3 | F | CF3 |
A-2125 | OCH3 | CF3 | CF3 | F | CF3 |
A-2126 | F | H | H | Cl | CF3 |
A-2127 | Cl | H | H | Cl | CF3 |
A-2128 | CH3 | H | H | Cl | CF3 |
A-2129 | CF3 | H | H | Cl | CF3 |
A-2130 | OCH3 | H | H | Cl | CF3 |
A-2131 | F | F | H | Cl | CF3 |
A-2132 | Cl | F | H | Cl | CF3 |
A-2133 | CH3 | F | H | Cl | CF3 |
A-2134 | CF3 | F | H | Cl | CF3 |
A-2135 | OCH3 | F | H | Cl | CF3 |
A-2136 | F | Cl | H | Cl | CF3 |
A-2137 | Cl | Cl | H | Cl | CF3 |
A-2138 | CH3 | Cl | H | Cl | CF3 |
A-2139 | CF3 | Cl | H | Cl | CF3 |
A-2140 | OCH3 | Cl | H | Cl | CF3 |
A-2141 | F | CH3 | H | Cl | CF3 |
A-2142 | Cl | CH3 | H | Cl | CF3 |
A-2143 | CH3 | CH3 | H | Cl | CF3 |
A-2144 | CF3 | CH3 | H | Cl | CF3 |
A-2145 | OCH3 | CH3 | H | Cl | CF3 |
A-2146 | F | CF3 | H | Cl | CF3 |
A-2147 | Cl | CF3 | H | Cl | CF3 |
A-2148 | CH3 | CF3 | H | Cl | CF3 |
A-2149 | CF3 | CF3 | H | Cl | CF3 |
A-2150 | OCH3 | CF3 | H | Cl | CF3 |
A-2151 | F | H | F | Cl | CF3 |
A-2152 | Cl | H | F | Cl | CF3 |
A-2153 | CH3 | H | F | Cl | CF3 |
A-2154 | CF3 | H | F | Cl | CF3 |
A-2155 | OCH3 | H | F | Cl | CF3 |
A-2156 | F | F | F | Cl | CF3 |
A-2157 | Cl | F | F | Cl | CF3 |
A-2158 | CH3 | F | F | Cl | CF3 |
A-2159 | CF3 | F | F | Cl | CF3 |
A-2160 | OCH3 | F | F | Cl | CF3 |
A-2161 | F | Cl | F | Cl | CF3 |
A-2162 | Cl | Cl | F | Cl | CF3 |
A-2163 | CH3 | Cl | F | Cl | CF3 |
A-2164 | CF3 | Cl | F | Cl | CF3 |
A-2165 | OCH3 | Cl | F | Cl | CF3 |
A-2166 | F | CH3 | F | Cl | CF3 |
A-2167 | Cl | CH3 | F | Cl | CF3 |
A-2168 | CH3 | CH3 | F | Cl | CF3 |
A-2169 | CF3 | CH3 | F | Cl | CF3 |
A-2170 | OCH3 | CH3 | F | Cl | CF3 |
A-2171 | F | CF3 | F | Cl | CF3 |
A-2172 | Cl | CF3 | F | Cl | CF3 |
A-2173 | CH3 | CF3 | F | Cl | CF3 |
A-2174 | CF3 | CF3 | F | Cl | CF3 |
A-2175 | OCH3 | CF3 | F | Cl | CF3 |
A-2176 | F | H | Cl | Cl | CF3 |
A-2177 | Cl | H | Cl | Cl | CF3 |
A-2178 | CH3 | H | Cl | Cl | CF3 |
A-2179 | CF3 | H | Cl | Cl | CF3 |
A-2180 | OCH3 | H | Cl | Cl | CF3 |
A-2181 | F | F | Cl | Cl | CF3 |
A-2182 | Cl | F | Cl | Cl | CF3 |
A-2183 | CH3 | F | Cl | Cl | CF3 |
A-2184 | CF3 | F | Cl | Cl | CF3 |
A-2185 | OCH3 | F | Cl | Cl | CF3 |
A-2186 | F | Cl | Cl | Cl | CF3 |
A-2187 | Cl | Cl | Cl | Cl | CF3 |
A-2188 | CH3 | Cl | Cl | Cl | CF3 |
A-2189 | CF3 | Cl | Cl | Cl | CF3 |
A-2190 | OCH3 | Cl | Cl | Cl | CF3 |
A-2191 | F | CH3 | Cl | Cl | CF3 |
A-2192 | Cl | CH3 | Cl | Cl | CF3 |
A-2193 | CH3 | CH3 | Cl | Cl | CF3 |
A-2194 | CF3 | CH3 | Cl | Cl | CF3 |
A-2195 | OCH3 | CH3 | Cl | Cl | CF3 |
A-2196 | F | CF3 | Cl | Cl | CF3 |
A-2197 | Cl | CF3 | Cl | Cl | CF3 |
A-2198 | CH3 | CF3 | Cl | Cl | CF3 |
A-2199 | CF3 | CF3 | Cl | Cl | CF3 |
A-2200 | OCH3 | CF3 | Cl | Cl | CF3 |
A-2201 | F | H | CH3 | Cl | CF3 |
A-2202 | Cl | H | CH3 | Cl | CF3 |
A-2203 | CH3 | H | CH3 | Cl | CF3 |
A-2204 | CF3 | H | CH3 | Cl | CF3 |
A-2205 | OCH3 | H | CH3 | Cl | CF3 |
A-2206 | F | F | CH3 | Cl | CF3 |
A-2207 | Cl | F | CH3 | Cl | CF3 |
A-2208 | CH3 | F | CH3 | Cl | CF3 |
A-2209 | CF3 | F | CH3 | Cl | CF3 |
A-2210 | OCH3 | F | CH3 | Cl | CF3 |
A-2211 | F | Cl | CH3 | Cl | CF3 |
A-2212 | Cl | Cl | CH3 | Cl | CF3 |
A-2213 | CH3 | Cl | CH3 | Cl | CF3 |
A-2214 | CF3 | Cl | CH3 | Cl | CF3 |
A-2215 | OCH3 | Cl | CH3 | Cl | CF3 |
A-2216 | F | CH3 | CH3 | Cl | CF3 |
A-2217 | Cl | CH3 | CH3 | Cl | CF3 |
A-2218 | CH3 | CH3 | CH3 | Cl | CF3 |
A-2219 | CF3 | CH3 | CH3 | Cl | CF3 |
A-2220 | OCH3 | CH3 | CH3 | Cl | CF3 |
A-2221 | F | CF3 | CH3 | Cl | CF3 |
A-2222 | Cl | CF3 | CH3 | Cl | CF3 |
A-2223 | CH3 | CF3 | CH3 | Cl | CF3 |
A-2224 | CF3 | CF3 | CH3 | Cl | CF3 |
A-2225 | OCH3 | CF3 | CH3 | Cl | CF3 |
A-2226 | F | H | CF3 | Cl | CF3 |
A-2227 | Cl | H | CF3 | Cl | CF3 |
A-2228 | CH3 | H | CF3 | Cl | CF3 |
A-2229 | CF3 | H | CF3 | Cl | CF3 |
A-2230 | OCH3 | H | CF3 | Cl | CF3 |
A-2231 | F | F | CF3 | Cl | CF3 |
A-2232 | Cl | F | CF3 | Cl | CF3 |
A-2233 | CH3 | F | CF3 | Cl | CF3 |
A-2234 | CF3 | F | CF3 | Cl | CF3 |
A-2235 | OCH3 | F | CF3 | Cl | CF3 |
A-2236 | F | Cl | CF3 | Cl | CF3 |
A-2237 | Cl | Cl | CF3 | Cl | CF3 |
A-2238 | CH3 | Cl | CF3 | Cl | CF3 |
A-2239 | CF3 | Cl | CF3 | Cl | CF3 |
A-2240 | OCH3 | Cl | CF3 | Cl | CF3 |
A-2241 | F | CH3 | CF3 | Cl | CF3 |
A-2242 | Cl | CH3 | CF3 | Cl | CF3 |
A-2243 | CH3 | CH3 | CF3 | Cl | CF3 |
A-2244 | CF3 | CH3 | CF3 | Cl | CF3 |
A-2245 | OCH3 | CH3 | CF3 | Cl | CF3 |
A-2246 | F | CF3 | CF3 | Cl | CF3 |
A-2247 | Cl | CF3 | CF3 | Cl | CF3 |
A-2248 | CH3 | CF3 | CF3 | Cl | CF3 |
A-2249 | CF3 | CF3 | CF3 | Cl | CF3 |
A-2250 | OCH3 | CF3 | CF3 | Cl | CF3 |
A-2251 | F | H | H | CH3 | CF3 |
A-2252 | Cl | H | H | CH3 | CF3 |
A-2253 | CH3 | H | H | CH3 | CF3 |
A-2254 | CF3 | H | H | CH3 | CF3 |
A-2255 | OCH3 | H | H | CH3 | CF3 |
A-2256 | F | F | H | CH3 | CF3 |
A-2257 | Cl | F | H | CH3 | CF3 |
A-2258 | CH3 | F | H | CH3 | CF3 |
A-2259 | CF3 | F | H | CH3 | CF3 |
A-2260 | OCH3 | F | H | CH3 | CF3 |
A-2261 | F | Cl | H | CH3 | CF3 |
A-2262 | Cl | Cl | H | CH3 | CF3 |
A-2263 | CH3 | Cl | H | CH3 | CF3 |
A-2264 | CF3 | Cl | H | CH3 | CF3 |
A-2265 | OCH3 | Cl | H | CH3 | CF3 |
A-2266 | F | CH3 | H | CH3 | CF3 |
A-2267 | Cl | CH3 | H | CH3 | CF3 |
A-2268 | CH3 | CH3 | H | CH3 | CF3 |
A-2269 | CF3 | CH3 | H | CH3 | CF3 |
A-2270 | OCH3 | CH3 | H | CH3 | CF3 |
A-2271 | F | CF3 | H | CH3 | CF3 |
A-2272 | Cl | CF3 | H | CH3 | CF3 |
A-2273 | CH3 | CF3 | H | CH3 | CF3 |
A-2274 | CF3 | CF3 | H | CH3 | CF3 |
A-2275 | OCH3 | CF3 | H | CH3 | CF3 |
A-2276 | F | H | F | CH3 | CF3 |
A-2277 | Cl | H | F | CH3 | CF3 |
A-2278 | CH3 | H | F | CH3 | CF3 |
A-2279 | CF3 | H | F | CH3 | CF3 |
A-2280 | OCH3 | H | F | CH3 | CF3 |
A-2281 | F | F | F | CH3 | CF3 |
A-2282 | Cl | F | F | CH3 | CF3 |
A-2283 | CH3 | F | F | CH3 | CF3 |
A-2284 | CF3 | F | F | CH3 | CF3 |
A-2285 | OCH3 | F | F | CH3 | CF3 |
A-2286 | F | Cl | F | CH3 | CF3 |
A-2287 | Cl | Cl | F | CH3 | CF3 |
A-2288 | CH3 | Cl | F | CH3 | CF3 |
A-2289 | CF3 | Cl | F | CH3 | CF3 |
A-2290 | OCH3 | Cl | F | CH3 | CF3 |
A-2291 | F | CH3 | F | CH3 | CF3 |
A-2292 | Cl | CH3 | F | CH3 | CF3 |
A-2293 | CH3 | CH3 | F | CH3 | CF3 |
A-2294 | CF3 | CH3 | F | CH3 | CF3 |
A-2295 | OCH3 | CH3 | F | CH3 | CF3 |
A-2296 | F | CF3 | F | CH3 | CF3 |
A-2297 | Cl | CF3 | F | CH3 | CF3 |
A-2298 | CH3 | CF3 | F | CH3 | CF3 |
A-2299 | CF3 | CF3 | F | CH3 | CF3 |
A-2300 | OCH3 | CF3 | F | CH3 | CF3 |
A-2301 | F | H | Cl | CH3 | CF3 |
A-2302 | Cl | H | Cl | CH3 | CF3 |
A-2303 | CH3 | H | Cl | CH3 | CF3 |
A-2304 | CF3 | H | Cl | CH3 | CF3 |
A-2305 | OCH3 | H | Cl | CH3 | CF3 |
A-2306 | F | F | Cl | CH3 | CF3 |
A-2307 | Cl | F | Cl | CH3 | CF3 |
A-2308 | CH3 | F | Cl | CH3 | CF3 |
A-2309 | CF3 | F | Cl | CH3 | CF3 |
A-2310 | OCH3 | F | Cl | CH3 | CF3 |
A-2311 | F | Cl | Cl | CH3 | CF3 |
A-2312 | Cl | Cl | Cl | CH3 | CF3 |
A-2313 | CH3 | Cl | Cl | CH3 | CF3 |
A-2314 | CF3 | Cl | Cl | CH3 | CF3 |
A-2315 | OCH3 | Cl | Cl | CH3 | CF3 |
A-2316 | F | CH3 | Cl | CH3 | CF3 |
A-2317 | Cl | CH3 | Cl | CH3 | CF3 |
A-2318 | CH3 | CH3 | Cl | CH3 | CF3 |
A-2319 | CF3 | CH3 | Cl | CH3 | CF3 |
A-2320 | OCH3 | CH3 | Cl | CH3 | CF3 |
A-2321 | F | CF3 | Cl | CH3 | CF3 |
A-2322 | Cl | CF3 | Cl | CH3 | CF3 |
A-2323 | CH3 | CF3 | Cl | CH3 | CF3 |
A-2324 | CF3 | CF3 | Cl | CH3 | CF3 |
A-2325 | OCH3 | CF3 | Cl | CH3 | CF3 |
A-2326 | F | H | CH3 | CH3 | CF3 |
A-2327 | Cl | H | CH3 | CH3 | CF3 |
A-2328 | CH3 | H | CH3 | CH3 | CF3 |
A-2329 | CF3 | H | CH3 | CH3 | CF3 |
A-2330 | OCH3 | H | CH3 | CH3 | CF3 |
A-2331 | F | F | CH3 | CH3 | CF3 |
A-2332 | Cl | F | CH3 | CH3 | CF3 |
A-2333 | CH3 | F | CH3 | CH3 | CF3 |
A-2334 | CF3 | F | CH3 | CH3 | CF3 |
A-2335 | OCH3 | F | CH3 | CH3 | CF3 |
A-2336 | F | Cl | CH3 | CH3 | CF3 |
A-2337 | Cl | Cl | CH3 | CH3 | CF3 |
A-2338 | CH3 | Cl | CH3 | CH3 | CF3 |
A-2339 | CF3 | Cl | CH3 | CH3 | CF3 |
A-2340 | OCH3 | Cl | CH3 | CH3 | CF3 |
A-2341 | F | CH3 | CH3 | CH3 | CF3 |
A-2342 | Cl | CH3 | CH3 | CH3 | CF3 |
A-2343 | CH3 | CH3 | CH3 | CH3 | CF3 |
A-2344 | CF3 | CH3 | CH3 | CH3 | CF3 |
A-2345 | OCH3 | CH3 | CH3 | CH3 | CF3 |
A-2346 | F | CF3 | CH3 | CH3 | CF3 |
A-2347 | Cl | CF3 | CH3 | CH3 | CF3 |
A-2348 | CH3 | CF3 | CH3 | CH3 | CF3 |
A-2349 | CF3 | CF3 | CH3 | CH3 | CF3 |
A-2350 | OCH3 | CF3 | CH3 | CH3 | CF3 |
A-2351 | F | H | CF3 | CH3 | CF3 |
A-2352 | Cl | H | CF3 | CH3 | CF3 |
A-2353 | CH3 | H | CF3 | CH3 | CF3 |
A-2354 | CF3 | H | CF3 | CH3 | CF3 |
A-2355 | OCH3 | H | CF3 | CH3 | CF3 |
A-2356 | F | F | CF3 | CH3 | CF3 |
A-2357 | Cl | F | CF3 | CH3 | CF3 |
A-2358 | CH3 | F | CF3 | CH3 | CF3 |
A-2359 | CF3 | F | CF3 | CH3 | CF3 |
A-2360 | OCH3 | F | CF3 | CH3 | CF3 |
A-2361 | F | Cl | CF3 | CH3 | CF3 |
A-2362 | Cl | Cl | CF3 | CH3 | CF3 |
A-2363 | CH3 | Cl | CF3 | CH3 | CF3 |
A-2364 | CF3 | Cl | CF3 | CH3 | CF3 |
A-2365 | OCH3 | Cl | CF3 | CH3 | CF3 |
A-2366 | F | CH3 | CF3 | CH3 | CF3 |
A-2367 | Cl | CH3 | CF3 | CH3 | CF3 |
A-2368 | CH3 | CH3 | CF3 | CH3 | CF3 |
A-2369 | CF3 | CH3 | CF3 | CH3 | CF3 |
A-2370 | OCH3 | CH3 | CF3 | CH3 | CF3 |
A-2371 | F | CF3 | CF3 | CH3 | CF3 |
A-2372 | Cl | CF3 | CF3 | CH3 | CF3 |
A-2373 | CH3 | CF3 | CF3 | CH3 | CF3 |
A-2374 | CF3 | CF3 | CF3 | CH3 | CF3 |
A-2375 | OCH3 | CF3 | CF3 | CH3 | CF3 |
A-2376 | F | H | H | CF3 | CF3 |
A-2377 | Cl | H | H | CF3 | CF3 |
A-2378 | CH3 | H | H | CF3 | CF3 |
A-2379 | CF3 | H | H | CF3 | CF3 |
A-2380 | OCH3 | H | H | CF3 | CF3 |
A-2381 | F | F | H | CF3 | CF3 |
A-2382 | Cl | F | H | CF3 | CF3 |
A-2383 | CH3 | F | H | CF3 | CF3 |
A-2384 | CF3 | F | H | CF3 | CF3 |
A-2385 | OCH3 | F | H | CF3 | CF3 |
A-2386 | F | Cl | H | CF3 | CF3 |
A-2387 | Cl | Cl | H | CF3 | CF3 |
A-2388 | CH3 | Cl | H | CF3 | CF3 |
A-2389 | CF3 | Cl | H | CF3 | CF3 |
A-2390 | OCH3 | Cl | H | CF3 | CF3 |
A-2391 | F | CH3 | H | CF3 | CF3 |
A-2392 | Cl | CH3 | H | CF3 | CF3 |
A-2393 | CH3 | CH3 | H | CF3 | CF3 |
A-2394 | CF3 | CH3 | H | CF3 | CF3 |
A-2395 | OCH3 | CH3 | H | CF3 | CF3 |
A-2396 | F | CF3 | H | CF3 | CF3 |
A-2397 | Cl | CF3 | H | CF3 | CF3 |
A-2398 | CH3 | CF3 | H | CF3 | CF3 |
A-2399 | CF3 | CF3 | H | CF3 | CF3 |
A-2400 | OCH3 | CF3 | H | CF3 | CF3 |
A-2401 | F | H | F | CF3 | CF3 |
A-2402 | Cl | H | F | CF3 | CF3 |
A-2403 | CH3 | H | F | CF3 | CF3 |
A-2404 | CF3 | H | F | CF3 | CF3 |
A-2405 | OCH3 | H | F | CF3 | CF3 |
A-2406 | F | F | F | CF3 | CF3 |
A-2407 | Cl | F | F | CF3 | CF3 |
A-2408 | CH3 | F | F | CF3 | CF3 |
A-2409 | CF3 | F | F | CF3 | CF3 |
A-2410 | OCH3 | F | F | CF3 | CF3 |
A-2411 | F | Cl | F | CF3 | CF3 |
A-2412 | Cl | Cl | F | CF3 | CF3 |
A-2413 | CH3 | Cl | F | CF3 | CF3 |
A-2414 | CF3 | Cl | F | CF3 | CF3 |
A-2415 | OCH3 | Cl | F | CF3 | CF3 |
A-2416 | F | CH3 | F | CF3 | CF3 |
A-2417 | Cl | CH3 | F | CF3 | CF3 |
A-2418 | CH3 | CH3 | F | CF3 | CF3 |
A-2419 | CF3 | CH3 | F | CF3 | CF3 |
A-2420 | OCH3 | CH3 | F | CF3 | CF3 |
A-2421 | F | CF3 | F | CF3 | CF3 |
A-2422 | Cl | CF3 | F | CF3 | CF3 |
A-2423 | CH3 | CF3 | F | CF3 | CF3 |
A-2424 | CF3 | CF3 | F | CF3 | CF3 |
A-2425 | OCH3 | CF3 | F | CF3 | CF3 |
A-2426 | F | H | Cl | CF3 | CF3 |
A-2427 | Cl | H | Cl | CF3 | CF3 |
A-2428 | CH3 | H | Cl | CF3 | CF3 |
A-2429 | CF3 | H | Cl | CF3 | CF3 |
A-2430 | OCH3 | H | Cl | CF3 | CF3 |
A-2431 | F | F | Cl | CF3 | CF3 |
A-2432 | Cl | F | Cl | CF3 | CF3 |
A-2433 | CH3 | F | Cl | CF3 | CF3 |
A-2434 | CF3 | F | Cl | CF3 | CF3 |
A-2435 | OCH3 | F | Cl | CF3 | CF3 |
A-2436 | F | Cl | Cl | CF3 | CF3 |
A-2437 | Cl | Cl | Cl | CF3 | CF3 |
A-2438 | CH3 | Cl | Cl | CF3 | CF3 |
A-2439 | CF3 | Cl | Cl | CF3 | CF3 |
A-2440 | OCH3 | Cl | Cl | CF3 | CF3 |
A-2441 | F | CH3 | Cl | CF3 | CF3 |
A-2442 | Cl | CH3 | Cl | CF3 | CF3 |
A-2443 | CH3 | CH3 | Cl | CF3 | CF3 |
A-2444 | CF3 | CH3 | Cl | CF3 | CF3 |
A-2445 | OCH3 | CH3 | Cl | CF3 | CF3 |
A-2446 | F | CF3 | Cl | CF3 | CF3 |
A-2447 | Cl | CF3 | Cl | CF3 | CF3 |
A-2448 | CH3 | CF3 | Cl | CF3 | CF3 |
A-2449 | CF3 | CF3 | Cl | CF3 | CF3 |
A-2450 | OCH3 | CF3 | Cl | CF3 | CF3 |
A-2451 | F | H | CH3 | CF3 | CF3 |
A-2452 | Cl | H | CH3 | CF3 | CF3 |
A-2453 | CH3 | H | CH3 | CF3 | CF3 |
A-2454 | CF3 | H | CH3 | CF3 | CF3 |
A-2455 | OCH3 | H | CH3 | CF3 | CF3 |
A-2456 | F | F | CH3 | CF3 | CF3 |
A-2457 | Cl | F | CH3 | CF3 | CF3 |
A-2458 | CH3 | F | CH3 | CF3 | CF3 |
A-2459 | CF3 | F | CH3 | CF3 | CF3 |
A-2460 | OCH3 | F | CH3 | CF3 | CF3 |
A-2461 | F | Cl | CH3 | CF3 | CF3 |
A-2462 | Cl | Cl | CH3 | CF3 | CF3 |
A-2463 | CH3 | Cl | CH3 | CF3 | CF3 |
A-2464 | CF3 | Cl | CH3 | CF3 | CF3 |
A-2465 | OCH3 | Cl | CH3 | CF3 | CF3 |
A-2466 | F | CH3 | CH3 | CF3 | CF3 |
A-2467 | Cl | CH3 | CH3 | CF3 | CF3 |
A-2468 | CH3 | CH3 | CH3 | CF3 | CF3 |
A-2469 | CF3 | CH3 | CH3 | CF3 | CF3 |
A-2470 | OCH3 | CH3 | CH3 | CF3 | CF3 |
A-2471 | F | CF3 | CH3 | CF3 | CF3 |
A-2472 | Cl | CF3 | CH3 | CF3 | CF3 |
A-2473 | CH3 | CF3 | CH3 | CF3 | CF3 |
A-2474 | CF3 | CF3 | CH3 | CF3 | CF3 |
A-2475 | OCH3 | CF3 | CH3 | CF3 | CF3 |
A-2476 | F | H | CF3 | CF3 | CF3 |
A-2477 | Cl | H | CF3 | CF3 | CF3 |
A-2478 | CF3 | H | CF3 | CF3 | CF3 |
A-2479 | CF3 | H | CF3 | CF3 | CF3 |
A-2480 | OCH3 | H | CF3 | CF3 | CF3 |
A-2481 | F | F | CF3 | CF3 | CF3 |
A-2482 | Cl | F | CF3 | CF3 | CF3 |
A-2483 | CH3 | F | CF3 | CF3 | CF3 |
A-2484 | CF3 | F | CF3 | CF3 | CF3 |
A-2485 | OCH3 | F | CF3 | CF3 | CF3 |
A-2486 | F | Cl | CF3 | CF3 | CF3 |
A-2487 | Cl | Cl | CF3 | CF3 | CF3 |
A-2488 | CH3 | Cl | CF3 | CF3 | CF3 |
A-2489 | CF3 | Cl | CF3 | CF3 | CF3 |
A-2490 | OCH3 | Cl | CF3 | CF3 | CF3 |
A-2491 | F | CH3 | CF3 | CF3 | CF3 |
A-2492 | Cl | CH3 | CF3 | CF3 | CF3 |
A-2493 | CH3 | CH3 | CF3 | CF3 | CF3 |
A-2494 | CF3 | CH3 | CF3 | CF3 | CF3 |
A-2495 | OCH3 | CH3 | CF3 | CF3 | CF3 |
A-2496 | F | CF3 | CF3 | CF3 | CF3 |
A-2497 | Cl | CF3 | CF3 | CF3 | CF3 |
A-2498 | CH3 | CF3 | CF3 | CF3 | CF3 |
A-2499 | CF3 | CF3 | CF3 | CF3 | CF3 |
A-2500 | OCH3 | CF3 | CF3 | CF3 | CF3 |
表B:优选的式I′.1化合物实例是式I′.1-B化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-B.1至I′.1-B.2500)。
表C:优选的式I′.1化合物实例是式I′.1-C化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-C.1至I′.1-C.2500)。
表D:优选的式I′.1化合物实例是式I′.1-D化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-D.1至I′.1-D.2500)。
表E:优选的式I′.1化合物实例是式I′.1-E化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-E.1至I′.1-E.2500)。
表F:优选的式I′.1化合物实例是式I′.1-F化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-F.1至I′.1-F.2500)。
表G:优选的式I′.1化合物实例是式I′.1-G化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-G.1至I′.1-G.2500)。
表H:优选的式I′.1化合物实例是式I′.1-H化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-H.1至I′.1-H.2500)。
表J:优选的式I′.1化合物实例是式I′.1-J化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-J.1至I′.1-J.2500)。
表K:优选的式I′.1化合物实例是式I′.1-K化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-K.1至I′.1-K.2500)。
表L:优选的式I′.1化合物实例是式I′.1-L化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-L.1至I′.1-L.2500)。
表M:优选的式I′.1化合物实例是式I′.1-M化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-M.1至I′.1-M.2500)。
表N:优选的式I′.1化合物实例是式I′.1-N化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-N.1至I′.1-N.2500)。
表O:优选的式I′.1化合物实例是式I′.1-O化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-O.1至I′.1-O.2500)。
表P:优选的式I′.1化合物实例是式I′.1-P化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-P.1至I′.1-P.2500)。
表Q:优选的式I′.1化合物实例是式I′.1-Q化合物:
其中R2、R3、R4、R5和R6具有对应于表1的一行的含义(化合物I′.1-Q.1至I′.1-Q.2500)。
式I化合物的制备可以根据方案1-4中所给实例完成,但不限于下面所给途径:
式I.1和I.2化合物例如可以根据WO 2005/63724所述的制备程序如方案1所示通过使式II.1化合物和/或其互变异构体II.2与式III化合物如烷基化剂、酰化剂等反应而制备。该反应的主要产物为式I.1化合物,其通常为分离的唯一异构体。
方案1
式II.1化合物及其式II.2的互变异构体例如可以由对应的二苯基乙基胺IV通过方案2和3所示合成途径制备。其中X为S的式II.1化合物及其式II.2的互变异构体可以根据方案2所示方法得到。
方案2:
根据方案2所示方法,通过常规方法将1,2-二苯基氨基乙烷IV转化成对应的异硫氰酸酯V,例如通过使IV与硫光气反应(例如参见Houben-Weyl,E4,“Methoden der Organischen Chemie”,第IIIc章,第837-842页)。然后使异硫氰酸酯V与式VI的氨基乙醇衍生物反应,由此得到式VII的硫脲化合物。氨基乙醇衍生物VI与异硫氰酸酯V的反应可以按照有机化学的标准方法进行,例如参见Biosci.Biotech.Biochem.1992,56(7),1062-1065。如此得到的硫脲可以通过常规方法环化,由此得到所需式II的噻唑啉化合物,其中X为S。化合物VII的环化可以例如在酸催化或在脱水条件下例如通过Mitsunobu反应实现(参见TetrahedronLetters1999,40,3125-3128)。
其中X为O的式II化合物可以通过方案3中所示方法得到。在方案3中,Y是指OH或卤素且Z是指氢、烷基或卤素,尤其是氟。
方案3
根据方案3,通过使II与氯甲酸苯基酯如氯甲酸4-氯苯基酯根据标准方法反应而将二苯基氨基乙烷IV转化成对应的式VIII的氨基甲酸酯(例如参见Pesticide Biochemistry and Physiology 30,1988,第190-197页)。使如此得到的氨基甲酸酯VIII与式VI的氨基乙醇衍生物在三甲基氯硅烷存在下根据J.Org.Chem.1998,63,8515-8521中所述的方法反应。由此得到式VII.a的2-羟基乙基脲{Y=OH}。2-羟基乙基脲可以根据Org.Lett.1999,1,1705-1708或Tetrahedron Lett.1992,33,2807-2810中所述的程序环化成噁唑啉化合物II。
或者,可以根据Bioorg.Med.Chem.Lett.1994,4,2317-2322中所述的方法使取代的2-氯乙基脲VII.a{Y=卤素}环化。
方案4
在方案4中,Hal为卤素,尤其是氯。可以通过与2-卤代乙基异氰酸酯IX,尤其是2-氯乙基异氰酸酯反应而由对应的式IV的二苯基乙基胺得到氯乙基脲VII.a。
式IV的二苯基乙基胺例如可以如方案5所示通过适当取代的阴离子等价物如有机金属化合物XII在适当取代的含C=N键化合物XI上加成而制备(例如参见Chem.Rev.1998,98,1407-1438)。
方案5
起始亚胺XI例如可以通过有机化学家熟知的方法由对应的醛X通过与胺在脱水剂存在下反应而制备或由腈通过还原而制备(例如J.Org.Chem.1990,55,4199-4200)并且在本领域是众所周知的。起始亚胺XI还包括例如如Tetrahedron 1999,55,8883-8904中所述的手性化合物。
由对应的羧酰胺制备类似于式IV胺的化合物的通用方法已经描述于US 4536599中。
式I.2化合物还可以例如通过还原性胺化将式IV的伯胺转化成式XIV的仲胺(参见方案6),然后加成式XV的适当取代的异硫氰酸酯如乙酰氧基乙基异硫氰酸酯以及随后皂化而得到。式XV的异硫氰酸酯例如可以根据Coll.Czech.Chem.Comm.1986,51,112-117中所述的程序制备。
如此得到的硫脲XVI可以通过常规方法环化,由此得到式I.2的唑啉化合物。化合物XVI的环化可以根据制备式II化合物的方案2所示反应实现。
方案6
或者如方案7所示,使异硫氰酸酯V(参见方案2)与式XVII的适当取代的氨基乙醇反应,由此得到硫脲XVIII。氨基乙醇XVII与异硫氰酸酯V的反应可以按照方案2所示方法进行。硫脲XVIII可以根据方案2或7所示方法转化成式I.1化合物。
方案7
或者,通式I.2的化合物可以根据方案8并且根据WO 2006/125748中所述类似程序制备或对于WO 2007/020377中类似的苄基氨基噻唑啉通过使适当取代的唑啉XIV(参见方案6)与唑啉化合物XIX反应而制备。
方案8
式I化合物通常可以通过上述方法制备。若单个化合物不能经由上述途径制备,则它们可以通过衍生其他式I化合物或通过所述合成途径的常规改变而制备。例如,在各种情况下,某些式I化合物可以有利地通过酯水解、酰胺化、酯化、醚裂解、烯烃化、还原、氧化等由其他式I化合物制备。
反应混合物以常规方式处理,例如通过与水混合,分离各相以及合适的话,通过例如在氧化铝或硅胶上的层析法提纯粗产物。一些中间体和终产物可能以无色或浅棕色粘稠油形式得到,将它们在减压和温和升高的温度下提纯或除去挥发性组分。若中间体和终产物以固体得到,则它们可以通过重结晶或浸提进行提纯。
由于其优异的活性,通式I的化合物可以用于防治动物害虫。
因此,本发明还提供了一种防治动物害虫的方法,该方法包括用杀虫有效量的如上所定义的式I化合物或其盐或组合物处理害虫、其食物供应源、其栖息地或其繁殖地或其中害虫生长或可能生长的植物、植物繁殖材料、土壤、区域、材料或环境或者要防止害虫侵袭或侵染的材料、植物、植物繁殖材料、土壤、表面或空间。
优选本发明方法用于保护植物繁殖材料,尤其是种子和由其生长的植物以防动物害虫侵袭或侵染且包括用杀虫有效量的如上所定义的式I化合物或其可农用盐或用杀虫有效量的如上文和下文所定义的农用组合物处理植物繁殖材料,尤其是种子。本发明方法不限于保护已经根据本发明处理的“底物”(植物、植物繁殖材料如种子、土壤材料等),而且还具有预防效果,因此例如可以保护由已处理植物繁殖材料生长的植物,但植物本身并未被处理。
就本发明而言,“动物害虫”优选选自节肢动物和线虫,更优选选自有害昆虫、蜘蛛和线虫,甚至更优选选自昆虫、螨虫和线虫。
本发明进一步提供了一种用于防治该类动物害虫的农用组合物,其包含具有杀虫作用量的至少一种通式I化合物或至少一种其可农用盐和至少一种惰性液体和/或固体可农用载体以及需要的话至少一种表面活性剂。
该组合物可以含有单一的式I活性化合物或其盐或几种本发明式I活性化合物或其盐的混合物。本发明组合物可以包含各异构体或异构体混合物以及各互变异构体或互变异构体的混合物。
式I化合物和包含它们的杀虫组合物是防治节肢动物害虫和线虫的有效试剂。由式I化合物防治的动物害虫例如包括:
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsiagemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphis unipuncta)、苹果小卷蛾(Cydiapomonella)、松毛虫(Dendrolimus pini)、Diaphania nitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetriabouliana、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(Heliothis virescens)、玉米穗虫(Heliothiszea)、菜螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantriacunea)、苹果巢蛾(Hyponomeuta malinellus)、番茄虫蛾(Keiferialycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletisblancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostegesticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、黄杉毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinianubilalis)、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)、草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoeapityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis;
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallussolstitialis、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)、长角叶甲(Diabroticalongicornis)、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(Ips typographus)、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(Diptera)),例如埃及伊蚊(Aedes aegypti)、剌扰伊蚊(Aedes vexans)、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(Gasterophilusintestinalis)、刺舌蝇(Glossina morsitans)、Haematobia irritans、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)、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、Phorbiaantiqua、萝卜蝇(Phorbia brassicae)、Phorbia coarctata、樱桃实蝇(Rhagoletis cerasl)、苹果实蝇(Rhagoletis pomonella)、牛虻(Tabanusbovinus)、Tipula oleracea和欧洲大蚊(Tipula paludosa);
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothrips corbetti)、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔梗蓟马(Scirtothrips citri)、稻蓟马(Thripsoryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci);
膜翅目昆虫(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athalia rosae)、切叶蚁(Atta cephalotes)、Atta sexdens、Atta texana、Hoplocampa minuta、Hoplocampa testudinea、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsis geminate)和红火蚁(Solenopsis invicta);
异翅目昆虫(异翅目(Heteroptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygasterintegriceps)、烟草蝽(Euschistus impictiventris)、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lyguspratensis)、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(Homoptera)),例如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、Aphis schneideri、卷叶蚜(Aphis spiraecola)、Aphis sambuci、豌豆蚜(Acyrthosiphon pisum)、马铃薯蚜(Aulacorthumsolani)、银叶粉虱(Bemisia argentifolii)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudusprunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosiphagossypii、Chaetosiphon fragaefolii、Cryptomyzus ribis、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulacorthum pseudosolani、Dysaphisplantaginea、Dysaphis pyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphumavenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphonrosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzusascalonicus)、Myzus cerasi、桃蚜(Myzus persicae)、李瘤蚜(Myzus varians)、Nasonovia ribisnigri、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigusbursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodonhumuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、Rhopalosiphum insertum、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneuralanuginosa、麦长管蚜(Sitobion avenae)、白背飞虱(Sogatella furcifera)、白粉虱(Trialeurodes vaporariorum)、Toxoptera aurantiiand和葡萄根瘤蚜(Viteus vitifolii);
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermes flavipes、黄肢散白蚁(Reticulitermes flavipes)、欧洲散白蚁(Reticulitermes lucifugus)和Termes natalensis;
直翅目昆虫(直翅目(Orthoptera)),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 femurrubrum)、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),
蜘蛛纲(Arachnoidea)如蜘蛛(蜱螨目(Acarina)),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),和瘿螨属(Eriophyidae)如苹果刺锈螨(Aculusschlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨属(Tarsonemidae)如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨属(Tenuipalpidae)如紫红短须螨(Brevipalpus phoenicis);叶螨属(Tetranychidae)如朱砂叶螨(Tetranychuscinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychuspacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri)和oligonychuspratensis;
蚤目(Siphonatera),例如印鼠客蚤(Xenopsylla cheopsis)、角叶属(Ceratophyllus);
组合物和式I化合物可用于防治线虫,尤其是植物寄生线虫如根结线虫,北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyneincognita)、爪哇根结线虫(Meloidogyne javanica)和其他根结线虫属(Meloidogyne);形成胞囊的线虫,马铃薯金线虫(Globodera rostochiensis)和其他球胞囊属(Globodera);禾谷胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、三叶草胞囊线虫(Heterodera trifolii)和其他胞囊线虫属(Heterodera);种子肿瘿线虫,粒线虫属(Anguina);茎叶线虫,滑刃线虫属(Aphelenchoides);刺线虫,杂草刺线虫(Belonolaimus longicaudatus)和其他针刺线虫属(Belonolaimus);松线虫,松材线虫(Bursaphelenchus xylophilus)和其他伞滑刃线虫属(Bursaphelenchus);环形线虫,环纹线虫属(Criconema)、小环线虫属(Criconemella)、轮线虫属(Criconemoides)、中环线虫属(Mesocriconema);球茎线虫,腐烂茎线虫(Ditylenchus destructor)、甘薯茎线虫(Ditylenchus dipsaci)和其他茎线虫属(Ditylenchus);锥线虫,锥线虫属(Dolichodorus);螺旋形线虫,Heliocotylenchus multicinctus和其他Helicotylenchus属;鞘线虫和鞘形(sheathoid)线虫,鞘线虫属(Hemicycliophora)和Hemicriconemoides属;Hirshmanniella属;冠线虫,Hoploaimus属;伪根结线虫,珍珠线虫属(Nacobbus);针线虫,Longidoruselongatus和其他长针线虫属(Longidorus);鞘线虫,针线虫属(Paratylenchus);根腐线虫,Pratylenchus neglectus、穿刺根腐线虫(Pratylenchus penetrans)、Pratylenchus curvitatus、Pratylenchus goodeyi和其他根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholussimilis)和其他穿孔线虫属(Radopholus);肾形线虫,Rotylenchus robustus和其他盘旋线虫属(Rotylenchus);Scutellonema属;残根线虫,Trichodorusprimitivus和其他毛刺线虫属(Trichodorus)、拟毛刺属(Paratrichodorus);阻长线虫,Tylenchorhynchus claytoni、Tylenchorhynchus dubius和其他矮化线虫属(Tylenchorhynchus);柑桔线虫,垫刃线虫属(Tylenchulus);剑线虫,剑线虫属(Xiphinema);以及其他植物寄生线虫。
在本发明的优选实施方案中,将式I化合物用于防治昆虫或蜘蛛,尤其是鳞翅目、鞘翅目、缨翅目和同翅目昆虫以及蜱螨目蜘蛛。本发明的式I化合物特别用于防治缨翅目和同翅目昆虫。
式I化合物或包含它们的杀虫组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的植物和作物以防动物害虫,尤其是昆虫、螨虫或蜘蛛侵袭或侵染。术语“作物”指生长和收获的作物二者。
可以将式I化合物转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的意欲目的;在每种情况下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(对于综述例如参见US 3,060,084,EP-A 707445(对于液体浓缩物),Browning,“Agglomeration”,ChemicalEngineering,1967年12月4日,147-48,Perry′s Chemical Engineer′sHandbook,第4版,McGraw-Hill,New York,1963,第8-57页及随后各页,WO 91/13546,US 4,172,714,US 4,144,050,US 3,920,442,US5,180,587,US 5,232,701,US 5,208,030,GB 2,095,558,US 3,299,566,Klingman,Weed Control as a Science,John Wiley and Sons,Inc.,NewYork,1961,Hance等,Weed Control Handbook,第8版,BlaekwellScientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology,Wiley VCH Verlag GmbH,Weinheim(德国),2001,2.D.A.Knowles,Chemistry and Technology of AgrochemicalFormulations,Kluwer Academic Publishers,Dordrecht,1998(ISBN0-7514-0443-8),例如通过将活性化合物与适合配制农用化学品的助剂如溶剂和/或载体,需要的话乳化剂、表面活性剂和分散剂、防腐剂、消泡剂、防冻剂、用于种子处理配制剂还有任选的着色剂和/或粘合剂和/或胶凝剂混合而制备。
合适溶剂的实例为水、芳族溶剂(例如Solvesso产品、二甲苯)、石蜡(例如矿物油馏分)、醇类(例如甲醇、丁醇、戊醇、苄醇)、酮类(例如环己酮、γ-丁内酯)、吡咯烷酮(N-甲基吡咯烷酮[NMP]、N-辛基吡咯烷酮[NOP])、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
合适乳化剂为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)。
分散剂的实例是木素亚硫酸盐废液和甲基纤维素。
所用的合适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,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化的异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/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。
适于制备可直接喷雾溶液、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,例如甲苯、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、环己醇、环己酮、异佛尔酮,强极性溶剂,例如二甲亚砜、N-甲基吡咯烷酮或水。
还可以将防冻剂如甘油、乙二醇、丙二醇和杀菌剂加入配制剂中。
合适的消泡剂例如为基于硅或硬脂酸镁的消泡剂。
合适的防腐剂例如为二氯芬。
种子处理配制剂可以额外包含粘合剂和任选的着色剂。
可以加入粘合剂以改进处理之后活性物质在种子上的粘附。合适的粘合剂是嵌段共聚物EO/PO表面活性剂以及聚乙烯醇、聚乙烯基吡咯烷酮、聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、聚乙烯亚胺(Lupasol、Polymin)、聚醚、聚氨酯、聚乙酸乙烯酯、纤基乙酸钠以及衍生于这些聚合物的共聚物。
任选还可以在配制剂中包括着色剂。对种子处理配制剂合适的着色剂或染料是若丹明B、C.I.颜料红112、C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红112、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
粉末、撒播用材料和可撒粉产品可以通过将活性物质与固体载体混合或同时研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过将活性化合物与固体载体粘附而制备。
固体载体的实例是矿土如硅胶、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,以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其他固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%活性化合物。此时,活性化合物以90-100重量%,优选95-100重量%的纯度(根据NMR光谱)使用。
对于种子处理目的,相应配制剂可以稀释2-10倍,从而在即用制剂中得到0.01-60重量%,优选0.1-40重量%的活性化合物浓度。
式I化合物可以直接、以其配制剂形式或由其制备的使用形式(例如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒形式),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;在任何情况下意欲确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助润湿剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而,还可以制备由活性物质、润湿剂、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浓缩物适于用水稀释。
即用制剂中的活性化合物浓度可在较宽范围内变化。它们通常为0.0001-10重量%,优选0.01-1重量%。
活性化合物也可成功用于超低容量法(ULV),其中可以施用包含超过95重量%活性化合物的配制剂,或甚至施用不含添加剂的活性化合物。
下列为配制剂实例:
1.叶面施用的用水稀释的产品。对于种子处理目的,该类产品可以稀释或不加稀释地施用于种子。
A)水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入润湿剂或其他助剂。活性化合物经水稀释溶解,从而得到含10重量%活性化合物的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体,从而得到含有20重量%活性化合物的配制剂。
C)可乳化浓缩物(EC)
将15重量份活性化合物溶于7重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液,从而得到含有15重量%活性化合物的配制剂。
D)乳液(EW、EO、ES)
将25重量份活性化合物溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(例如Ultraturrax)将该混合物引入30重量份水中并制成均相乳液。用水稀释得到乳液,从而得到含有25重量%活性化合物的配制剂。
E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂、润湿剂和70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液,从而得到含有20重量%活性化合物的配制剂。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物细碎研磨并加入50重量份分散剂和润湿剂,借助工业装置(例如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液,从而得到含有50重量%活性化合物的配制剂。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、润湿剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液,从而得到含有75重量%活性化合物的配制剂。
H)凝胶配制剂(GF)
在搅拌的球磨机中将20重量份活性化合物研磨,加入10重量份分散剂、1重量份胶凝剂润湿剂和70重量份水或有机溶剂,得到细活性化合物悬浮液。用水稀释得到活性化合物的稳定悬浮液,从而得到活性化合物含量为20重量%的配制剂。
2.叶面施用的不经稀释而施用的产品。对于种子处理目的,该类产品可以稀释或不加稀释地施用于种子。
I)可撒粉粉末(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到含有5重量%活性化合物的可撒粉产品。
J)颗粒(GR、FG、GG、MG)
将0.5重量份活性化合物细碎研磨并结合95.5重量份载体,从而得到含有0.5重量%活性化合物的配制剂。现行方法是挤出、喷雾干燥或流化床方法。这得到叶面使用的不经稀释而施用的颗粒。
K)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到含有10重量%活性化合物的产品,其不经稀释而施用于叶面。
式I化合物还适合处理植物繁殖材料如种子。常规的种子处理配制剂包括例如可流动浓缩物FS、溶液LS、干处理用粉末DS、淤浆处理用水分散性粉末WS、水溶性粉末SS以及乳液ES和EC和凝胶配制剂GF。这些配制剂可以经稀释或不经稀释地施用于种子。施用于种子在播种之前直接对种子或在后者预萌发之后进行。
在优选实施方案中,将FS配制剂用于种子处理。FS配制剂通常可以包含1-800g/l活性成分,1-200g/l表面活性剂,0-200g/l防冻剂,0-400g/l粘合剂,0-200g/l颜料和至多1升溶剂,优选水。
用于种子处理的式I化合物的其他优选FS配制剂包含0.5-80重量%活性成分,0.05-5重量%润湿剂,0.5-15重量%分散剂,0.1-5重量%增稠剂,5-20重量%防冻剂,0.1-2重量%消泡剂,1-20重量%颜料和/或染料,0-15重量%粘着剂/粘附剂,0-75重量%填料/赋形剂和0.01-1重量%防腐剂。
各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其他农药或杀菌剂都可加入活性成分中,若合适的话,恰在紧临使用前加入(桶混合)。这些试剂通常与本发明试剂以1∶10-10∶1的重量比混合。
式I化合物通过接触(经由土壤、玻璃、墙壁、床网、地毯、植物部分或动物部分)和摄取(诱饵或植物部分)而有效。
为了用于蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀或蟑螂,优选将式I化合物用于诱饵组合物中。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。固体诱饵可以制成各种适合相应用途的形状和形式如颗粒、块、棒、片。液体诱饵可以填充到各种装置中以确保适当施用,例如敞开容器、喷雾装置、液滴供应源或蒸发源。凝胶可以基于含水基质或油性基质且可以按照粘性、水分保留或老化特性根据特定要求配制。
用于组合物中的诱饵是具有足够的吸引力以刺激诸如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀等的昆虫或蟑螂食用它的产品。吸引力可以通过使用进食刺激剂或性信息素控制。食物刺激剂例如并不穷举地选自动物和/或植物蛋白质(肉-、鱼-或血液膳食,昆虫部分、蛋黄)、动物和/或植物来源的脂肪和油或单-、低聚-或聚有机糖类,尤其是蔗糖、乳糖、果糖、右旋糖、葡萄糖、淀粉、果胶或甚至糖蜜或蜂蜜。水果、作物、植物、动物、昆虫的新鲜或腐败部分或其特定部分也可以用作进食刺激剂。已知性信息素更具昆虫特异性。特殊信息素描述于文献中并且对本领域熟练技术人员是已知的。
式I化合物的配制剂如气雾剂(例如在喷雾罐中)、油喷雾剂或泵喷雾剂高度适于非专业使用者来防治害虫如蝇、跳蚤、蜱、蚊子或蟑螂。气雾剂配方优选由如下组分组成:活性化合物,溶剂如低级醇(例如甲醇、乙醇、丙醇、丁醇),酮类(例如丙酮、甲基乙基酮),沸程为约50-250℃的链烷烃(例如煤油),二甲基甲酰胺,N-甲基吡咯烷酮,二甲亚砜,芳族烃类如甲苯、二甲苯,水,此外还有助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7mol氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,芳香油如精油,中等脂肪酸与低级醇的酯,芳族羰基化合物,合适的话还有稳定剂如苯甲酸钠,两性表面活性剂,低级环氧化物,原甲酸三乙酯和需要的话推进剂如丙烷、丁烷、氮气、压缩空气、二甲醚、二氧化碳、氧化亚氮或这些气体的混合物。
油喷雾配制剂与气雾剂配方的不同在于没有使用推进剂。
式I化合物及其相应的组合物还可以用于蚊香片和熏蒸片,发烟盒、蒸发器板或长效蒸发器以及扑蛾纸、扑蛾垫或其他与热无关的蒸发器体系中。
用式I化合物及其相应组合物控制由昆虫传递的传染性疾病(例如疟疾、登革热和黄热病,淋巴丝虫病以及利什曼病)的方法也包括处理棚屋和房子的表面、空气喷雾和浸渍窗帘、帐篷、衣物、床品、采采蝇网等。施用于纤维、织物、编织物、无纺织物、网状材料或箔以及篷布上的杀虫组合物优选包含包括杀虫剂、任选的驱除剂和至少一种粘合剂的混合物。合适的驱除剂例如为N,N-二乙基-间甲苯甲酰胺(DEET),N,N-二乙基苯基乙酰胺(DEPA),1-(3-环己烷-1-基羰基)-2-甲基哌啶,(2-羟基甲基环己基)乙酸内酯,2-乙基-1,3-己二醇,避虫酮,甲基新癸酰胺(MNDA),不用于昆虫防治的拟除虫菊酯如{(+/-)-3-烯丙基-2-甲基-4-氧代环戊-2-(+)-烯基-(+)-反式-菊酸酯(Esbiothrin),衍生于植物提取物或与植物提取物相同的驱除剂如1,8-萜二烯、丁子香酚、(+)-Eucamalol(1)、(-)-1-表-eucamalol,或来自诸如花皮桉(Eucalyptus maculata)、蔓荆(Vitex rotundifolia)、Cymbopoganmartinii、香茅(Cymbopogan citratus)(柠檬草)、亚香茅(Cymopogannartdus(香茅))的植物的粗植物提取物。合适的粘合剂例如选自如下单体的聚合物和共聚物:脂族酸的乙烯基酯(例如乙酸乙烯酯和支链烷烃脂肪酸乙烯基酯),醇的丙烯酸和甲基丙烯酸酯如丙烯酸丁酯、丙烯酸2-乙基己基酯和丙烯酸甲酯,单烯属和二烯属不饱和烃如苯乙烯,以及脂族二烯烃如丁二烯。
窗帘和床品的浸渍通常通过将纺织材料浸入式I化合物的乳液或分散体中或将它们喷雾于床品上而进行。
可以用于处理种子的方法原则上是所有本领域已知的合适种子处理技术,尤其是拌种技术如种子涂敷(例如种子压丸)、种子撒粉和种子浸渗(例如种子浸泡)。这里“种子处理”指所有使种子和式I化合物相互接触的方法,而“拌种”指为种子提供一定量式I化合物的种子处理方法,即产生包含式I化合物的种子的方法。原则上可以在从种子收获到播种的任何时间对种子进行处理。种子可以在紧临播种前或在播种过程中处理,例如使用“播种箱”方法。然而,还可以在播种之前几个星期或几个月,例如播种之前至多12个月进行处理,例如以拌种处理形式进行,此时没有观察到效力显著降低。
有利的是,对未播种的种子进行处理。本文所用术语“未播种的种子”意欲包括从种子收获到为萌发和植物生长的目的而播种种子的任何时间段的种子。
具体而言,在处理中采取如下程序:在合适的装置如用于固体或固体/液体混合配对的混合装置中将种子与所需量的种子处理配制剂直接或在预先用水稀释之后混合,直到组合物均匀分布于种子上。合适的话,然后进行干燥步骤。
式I化合物或其对映体或可兽用盐尤其还适合用于在动物中和动物上防治寄生虫。
因此,本发明的另一目的是提供在动物中和动物上防治寄生虫的新方法。本发明的另一目的是提供对动物更安全的杀虫剂。本发明的另一目的进一步在于提供可以与现有杀虫剂相比以更低剂量使用的动物用杀虫剂。本发明的另一目的是提供对寄生虫提供更长的残留防治的动物用杀虫剂。
本发明还涉及用于在动物中和动物上防治寄生虫的含有杀寄生虫有效量的式I化合物或其对映体、非对映体或可兽用盐和可接受的载体的组合物。
本发明还提供了一种处理、防治、预防和保护动物以免受寄生虫侵袭和侵染的方法,包括对动物口服、局部或肠胃外给药或施用杀寄生虫有效量的式I化合物或其对映体、非对映体或可兽用盐或包含它的组合物。
本发明还提供了一种制备用于处理、防治、预防或保护动物以免受寄生虫侵袭或侵染的组合物的方法,该组合物包含杀寄生虫有效量的式I化合物或其对映体、非对映体或可兽用盐或包含它的组合物。
化合物对抗农业害虫的活性并不意味着它们适合在动物中和动物上防治体内和体外寄生虫,后者要求例如在口服施用情况下的非催吐低剂量,与动物的代谢相容性,低毒性和安全处理。
惊人的是,现已发现式I化合物适合在动物中和动物上防治体内和体外寄生虫。
式I化合物或其对映体、非对映体或可兽用盐以及包含它们的组合物优选用于在包括温血动物(包括人)在内的动物和鱼中防治和预防侵袭和侵染。它们例如适于在哺乳动物如牛、绵羊、猪、骆驼、鹿、马、小猪、家禽、兔、山羊、狗和猫,水牛、驴、黇鹿和驯鹿,以及产皮动物如貂、丝鼠和浣熊,禽类如母鸡、鹅、火鸡和鸭以及鱼类如淡水鱼和咸水鱼如鲑鱼、鲤鱼和鳗鱼中防治和预防侵袭和侵染。
式I化合物或其对映体、非对映体或可兽用盐以及包含它们的组合物优选用于在家养动物如狗或猫中防治和预防侵袭和侵染。
在温血动物和鱼类中的侵袭包括但不限于虱、咬虱、蜱、羊鼻蝇蛆、羊蜱蝇、螯蝇、家蝇、蝇、myiasitic蝇幼虫、恙螨、蚋、蚊和蚤。
式I化合物或其对映体、非对映体或可兽用盐以及包含它们的组合物适于内吸和/或非内吸控制体外和/或体内寄生虫。它们对所有或部分发育阶段有效。
式I化合物、其对映体、非对映体或可兽用盐尤其可以用于防治体外寄生虫。
式I化合物、其对映体、非对映体或可兽用盐尤其可以用于分别防治下列目和属的寄生虫:
蚤(蚤(Siphonaptera)),例如猫蚤(Ctenocephalides felis)、狗蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulexirritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus),蟑螂(蜚蠊目(Blattaria)-Blattodea),例如德国小蠊(Blattella germanica)、Blattella asahinae、美洲蟑螂(Periplaneta americana)、日本大蠊(Periplaneta japonica)、棕色蜚蠊(Periplaneta brunnea)、Periplanetafuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blattaorientalis),
苍蝇、蚊子(双翅目),例如埃及伊蚊、白纹伊蚊(Aedes albopictus)、刺扰伊蚊、墨西哥果蝇、五斑按蚊、Anopheles crucians、白足按蚊(Anophelesalbimanus)、疟蚊(Anopheles Gambiae)、Anopheles freeborni、白踝按蚊(Anopheles leucosphyrus)、微小按蚊(Anopheles minimus)、四斑按蚊(Anopheles quadrimaculatus)、红头丽蝇(Calliphora vicina)、蛆症金蝇、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysops silacea、Chrysops atlanticus、Cochliomyia hominivorax、Cordylobia anthropophaga、Culicoides furens、尖音库蚊、斑蚊(Culexnigripalpus)、致倦库蚊(Culex quinquefasciatus)、媒斑蚊(Culex tarsalis)、Culiseta inornata、Culiseta melanura、Dermatobia hominis、小毛厕蝇、马蝇、刺舌蝇、须舌蝇(Glossina palpalis)、Glossina fuscipes、Glossinatachinoides、Haematobia irritans、Haplodiplosis equestris、Hippelates属、纹皮蝇、Leptoconops torrens、Lucilia caprina、铜绿蝇、丝光绿蝇、Lycoriapectoralis、沼蚊属(Mansonia)、家蝇、厩腐蝇、羊狂蝇、Phlebotomusargentipes、Psorophora columbiae、Psorophora discolor、Prosimuliummixtum、红尾肉蝇(Sarcophaga haemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇(Stomoxys calcitrans)、牛虻、Tabanus atratus、红色原虻(Tabanus lineola)和Tabanus similis,
虱(毛虱目(Phthiraptera)),例如Pediculus humanus capitis、Pediculushumanus corporis、阴虱(Pthirus pubis)、Haematopinus eurysternus、Haematopinus suis、Linognathus vituli、Bovicola bovis、Menopon gallinae、Menacanthus stramineus和Solenopotes capillatus,
壁虱和寄生螨(寄螨目(Parasitiformes)):壁虱(蜱亚目(Ixodida)),例如黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、太平洋硬蜱(Ixodespacificus)、棕色犬壁虱(Rhiphicephalus sanguineus)、安氏革螨(Dermacentor andersoni)、美洲大革螨(Dermacentor variabilis)、长星形壁虱(Amblyomma americanum)、Ambryomma maculatum、Ornithodorushermsi、Ornithodorus turicata以及寄生螨(甲螨亚目(Mesostigmata)),例如柏氏禽刺螨(Ornithonyssus bacoti)和鸡皮刺螨(Dermanyssus gallinae);辐螨亚目(Actinedida)(前气门亚目(Prostigmata))和粉螨亚目(Acaridida)(无气门目(Astigmata)),例如Acarapis属、Cheyletiella属、Ornithocheyletia属、鼠螨属(Myobia)、Psorergates属、蠕形螨属(Demodex)、恙螨属(Trombicula)、Listrophorus属、粉螨属(Acarus)、食酪螨属(Tyrophagus)、嗜木螨属(Caloglyphus)、Hypodectes属、Pterolichus属、痒螨属(Psoroptes)、疥螨属(Chorioptes)、耳痒螨属(Otodectes)、Sarcoptes属、背肛螨属(Notoedres)、膝螨属(Knemidocoptes)、Cytodites属和Laminosioptes属,
臭虫(Heteropterida):温带臭虫(Cimex lectularius)、热带臭虫(Cimexhemipterus)、Reduvius senilis、锥蝽属(Triatoma)、锥蝽属(Rhodnius)、Panstrongylus属和Arilus critatus,
虱目(Anoplurida),例如Haematopinus属、Linognathus属、Pediculus属、Phtirus属和Solenopotes属,
食毛目(Mallophagida)(Arnblycerina和Ischnocerina亚目),例如Trimenopon属、Menopon属、Trinoton属、Bovicola属、Werneckiella属、Lepikentron属、Trichodectes属和Felicola属,
蛔虫(Nematoda):
金针虫和Trichinosis(毛管目(Trichosyringida)),例如毛形科(Trichinellidae)(毛形属(Trichinella))、毛首科(Trichuridae)、Trichuris属、毛细线虫属(Capillaria),
杆形目(Rhabditida),例如小杆线虫属(Rhabditis)、Strongyloides属、Helicephalobus属,
圆线虫目(Strongylida),例如Strongylus属、Ancylostoma属、美洲钩虫(Necator americanus)、Bunostomum属(钩虫)、毛圆线虫属(Trichostrongylus)、捻转血矛线虫(Haemonchus contortus)、Ostertagia属、Cooperia属、细颈线虫属(Nematodirus)、Dictyocaulus属、Cyathostoma属、结节线虫属(Oesophagostomum)、猪肾虫(Stephanurus dentatus)、Ollulanus属、夏伯特线虫属(Chabertia)、猪肾虫、气管比翼线虫(Syngamustrachea)、Ancylostoma属、钩虫属(Uncinaria)、球首线虫属(Globocephalus)、Necator属、后圆线虫属(Metastrongylus)、毛样缪勒线虫(Muellerius capillaris)、Protostrongylus属、管圆线虫属(Angiostrongylus)、Parelaphostrongylus属、Aleurostrongylus abstrusus和肾膨结线虫(Dioctophyma renal),
肠线虫(蛔目(Ascaridida)),例如似蚓蛔线虫(Ascaris lumbricoides)、猪蛔虫(Ascaris suum)、鸡蛔虫(Ascaridia galli)、马副蛔虫(Parascarisequorum)、蛲虫(Enterobius vermicularis)(蛲虫)、犬弓首蛔虫(Toxocaracanis)、犬蛔虫(Toxascaris leonine)、Skrjabinema属和马尖尾线虫(Oxyurisequi),
Camallanida,例如Dracunculus medinensis(麦地那龙线虫),
旋尾目(Spirurida),例如Thelazia属、丝虫属(Wuchereria)、Brugia属、Onchocerca属、Dirofilari属、Dipetalonema属、Setaria属、Elaeophora属、狼尾旋线虫(Spirocerca lupi)和丽线虫属(Habronema),
棘头虫(棘头动物门(Acanthocephala)),例如Acanthocephalus属、猪巨吻棘头虫(Macracanthorhynchus hirudinaceus)和棘头虫属(Oncicola),
扁虫类(Planarians)(扁形动物门(Plathelminthes)):
肝吸虫(Flukes)(吸虫纲(Trematoda)),例如肝片形吸虫属(Faciola)、Fascioloides magna、并殖吸虫属(Paragonimus)、双腔吸虫属(Dicrocoelium)、布氏姜片吸虫(Fasciolopsis buski)、华枝睾吸虫(Clonorchissinensis)、血吸虫属(Schistosoma)、毛毕吸虫属(Trichobilhar-zia)、有翼翼形吸虫(Alaria alata)、并殖吸虫属和Nanocyetes属,
Cercomeromorpha,尤其是Cestoda(绦虫),例如裂头绦虫属(Diphyllobothrium)、Tenia属、棘球绦虫属(Echinococcus)、犬复孔绦虫(Dipylidium caninum)、Multiceps属、膜壳绦虫属(Hymenolepis)、中殖孔绦虫属(Mesocestoides)、Vampirolepis属、Moniezia属、Anoplocephala属、Sirometra属、Anoplocephala属和Hymenolepis属。
式I化合物和包含它们的组合物尤其可用于防治双翅目、蚤目和蜱亚目的害虫。
此外,尤其优选式I化合物以及包含它们的组合物在防治蚊子中的用途。
式I化合物、其对映体、非对映体或可兽用盐以及包含它们的组合物在防治蝇中的用途是本发明的另一优选实施方案。
此外,尤其优选式I化合物、其对映体、非对映体或可兽用盐以及包含它们的组合物在防治蚤中的用途。
式I化合物、其对映体、非对映体或可兽用盐以及包含它们的组合物在防治壁虱中的用途是本发明的另一优选实施方案。
式I化合物、其对映体、非对映体或可兽用盐还尤其可以用于防治体内寄生虫(蛔虫、棘头虫和扁虫类)。
给药可以预防和治疗方式进行。
活性化合物的给药直接或以合适的制剂形式口服、局部/经皮或肠胃外进行。
为了对温血动物口服给药,可以将式I化合物、其对映体、非对映体或可兽用盐配制成动物饲料、动物饲料预混物、动物饲料浓缩物、丸剂、溶液、糊、悬浮液、浸液、凝胶、片剂、大丸剂和胶囊。此外,式I化合物可以在其饮用水中给药于动物。对于口服给药,所选择的剂型应为动物提供0.01-100mg/kg动物体重/天,优选0.5-100mg/kg动物体重/天的式I化合物(同样还有其对映体、非对映体或可兽用盐)。
或者,式I化合物、其对映体、非对映体或可兽用盐可以肠胃外给药于动物,例如通过腔内、肌内、静脉内或皮下注射。式I化合物、其对映体、非对映体或可兽用盐可以分散或溶于对于皮下注射而言生理上可接受的载体中。或者,式I化合物、其对映体、非对映体或可兽用盐可配制成皮下给药用植入物。此外,式I化合物、其对映体、非对映体或可兽用盐可以透皮给药于动物。对于肠胃外给药,所选剂型应为动物提供0.01-100mg/kg动物体重/天的式I化合物(或其对映体、非对映体或可兽用盐)。
式I化合物(同样还有其对映体、非对映体或可兽用盐)还可以浸液、粉剂、粉末、套环、挂牌(medallions)、喷雾剂、香波、滴施(spot-on)和喷淋(pour-on)配制剂形式以及以软膏或水包油或油包水乳液局部给药于动物。对于局部施用,浸液和喷雾剂通常含有0.5-5000ppm,优选1-3000ppm式I化合物。此外,式I化合物、其对映体、非对映体或可兽用盐可以配制成动物,特别是四足动物如牛和绵羊用耳贴。
合适的制剂是:
-溶液如口服溶液、稀释后口服给药用浓缩物、用于皮肤上或用于体腔内的溶液、喷淋配制剂、凝胶;
-口服或皮肤给药乳液和悬浮液;半固体制剂;
-其中将活性化合物在软膏基质中或在水包油或油包水乳液基质中加工的配制剂;
-固体制剂如粉末、预混物或浓缩物、颗粒、丸剂、片剂、大丸剂、胶囊;
气雾剂和吸入剂,以及含有活性化合物的成型制品。
适合注射的组合物通过将活性成分溶于合适的溶剂中并任选加入其他成分如酸、碱、缓冲盐、防腐剂和加溶剂而制备。过滤这些溶液并无菌填充。
合适的溶剂是生理上耐受的溶剂如水,链烷醇如乙醇、丁醇、苄醇、甘油、丙二醇、聚乙二醇、N-甲基吡咯烷酮、2-吡咯烷酮及其混合物。
活性化合物可以任选溶于生理上耐受的且适合注射的植物或合成油中。
合适的加溶剂是促进活性化合物在主溶剂中溶解或防止其沉淀的溶剂。实例是聚乙烯基吡咯烷酮、聚乙烯醇、聚氧乙基化蓖麻油和聚氧乙基化脱水山梨糖醇酯。
合适的防腐剂是苄醇、三氯丁醇、对羟基苯甲酸酯和正丁醇。
口服溶液直接给药。浓缩物在预先稀释至使用浓度之后口服给药。口服溶液和浓缩物根据现有技术以及上面对注射液所述制备,并不必需无菌程序。
用于皮肤上的溶液滴施、涂施、擦施、洒施或喷施。
用于皮肤上的溶液根据现有技术以及上面对注射液所述制备,并不必需无菌程序。
其他合适的溶剂是聚丙二醇,苯基乙醇,苯氧基乙醇,酯类如乙酸乙酯或乙酸丁酯、苯甲酸苄基酯,醚类如亚烷基二醇烷基醚,例如二丙二醇单甲醚,酮类如丙酮、甲基乙基酮,芳族烃类,植物和合成油,二甲基甲酰胺(DMF),二甲基乙酰胺,乙二醇单乙基醚(transcutol),丙酮缩甘油(solketal),碳酸亚丙基酯,以及它们的混合物。
可能有利的是在制备过程中加入增稠剂。合适的增稠剂是无机增稠剂如膨润土、胶态硅酸、单硬脂酸铝,有机增稠剂如纤维素衍生物、聚乙烯醇及其共聚物、丙烯酸酯和甲基丙烯酸酯。
将凝胶施加或涂敷在皮肤上或引入体腔中。凝胶通过用足以得到具有软膏状稠度的透明材料的增稠剂处理如在注射液情况下所述制备的溶液而制备。所用增稠剂是上面所给增稠剂。
将喷淋配制剂倒在或喷雾在限定的皮肤区域,活性化合物渗透进皮肤并内吸起作用。
喷淋配制剂通过将活性化合物在合适的皮肤相容性溶剂或溶剂混合物中溶解、悬浮或乳化而制备。合适的话加入其他助剂如着色剂、生物吸收促进物质、抗氧化剂、光稳定剂、粘合剂。
合适的溶剂是水,链烷醇,二醇,聚乙二醇,聚丙二醇,甘油,芳族醇如苄醇,苯基乙醇,苯氧基乙醇,酯如乙酸乙酯、乙酸丁酯、苯甲酸苄基酯,醚类如亚烷基二醇烷基醚如二丙二醇单甲基醚、二甘醇单丁基醚,酮类如丙酮、甲基乙基酮,环状碳酸酯如碳酸亚丙基酯、碳酸亚乙基酯,芳族和/或脂族烃类,植物或合成油,DMF,二甲基乙酰胺,正烷基吡咯烷酮如甲基吡咯烷酮、正丁基吡咯烷酮或正辛基吡咯烷酮、N-甲基吡咯烷酮、2-吡咯烷酮、2,2-二甲基-4-氧基亚甲基-1,3-二氧戊环和甘油缩甲醛。
合适的着色剂是所有允许用在动物上且可以溶解或悬浮的着色剂。
合适的吸收促进物质例如为DMSO,涂施油如肉豆蔻酸异丙基酯、二丙二醇壬酸酯、硅油及其与聚醚的共聚物,脂肪酸酯,甘油三酯,脂肪醇。
合适的抗氧化剂是亚硫酸盐或偏亚硫酸氢盐如偏亚硫酸氢钾、抗坏血酸、丁基羟基甲苯、丁基羟基茴香醚、生育酚。
合适的光稳定剂例如为2-苯基苯并咪唑-5-磺酸(novantisolic acid)。
合适的粘合剂例如为纤维素衍生物、淀粉衍生物、聚丙烯酸酯、天然聚合物如藻酸盐、明胶。
乳液可以口服、经皮给药或作为注射液给药。
乳液呈油包水型或水包油型。
它们通过将活性化合物溶于疏水或亲水相中并借助合适的乳化剂以及合适的话其他助剂如着色剂、吸收促进物质、防腐剂、抗氧化剂、光稳定剂、粘度提高物质用另一相的溶剂均化而制备。
合适的疏水相(油)是:
液体石蜡,硅油,天然植物油如芝麻油、杏仁油、蓖麻油,合成甘油三酯如甘油二辛酸/癸酸酯,含链长为C8-C12的植物脂肪酸或其他具体选定的天然脂肪酸的甘油三酯混合物,可能的话还含有羟基的饱和或不饱和脂肪酸的部分甘油酯混合物,C8-C10脂肪酸的甘油单酯和甘油二酯,脂肪酸酯如硬脂酸乙基酯、己二酸二正丁基酯、月桂酸己基酯、二丙二醇壬酸酯、中等链长的支化脂肪酸与链长为C16-C18的饱和脂肪醇的酯、肉豆蔻酸异丙基酯、棕榈酸异丙基酯、链长为C12-C18的饱和脂肪醇的辛酸/癸酸酯、硬脂酸异丙基酯、油酸油基酯、油酸癸基酯、油酸乙基酯、乳酸乙基酯、蜡状脂肪酸酯如合成鸭尾脂腺脂肪、邻苯二甲酸二丁酯、己二酸二异丙基酯以及与后者相关的酯混合物,
脂肪醇如异十三烷醇、2-辛基十二烷醇、十六烷基十八烷基醇、油醇,以及
脂肪酸如油酸,和
它们的混合物。
合适的亲水相是水,醇如丙二醇、甘油、山梨醇及其混合物。
合适的乳化剂是:
-非离子表面活性剂,例如聚乙氧基化蓖麻油、聚乙氧基化脱水山梨糖醇单油酸酯、脱水山梨糖醇单硬脂酸酯、甘油单硬脂酸酯、聚氧乙基硬脂酸酯、烷基酚聚乙二醇醚;
-两性表面活性剂,例如N-月桂基对亚氨基二丙酸二钠或卵磷脂;
-阴离子表面活性剂,例如月桂基硫酸钠、脂肪醇醚硫酸盐、聚乙二醇单/二烷基醚正磷酸酯单乙醇胺盐;
-阳离子表面活性剂如十六烷基三甲基氯化铵。
合适的其他助剂是提高粘度并稳定乳液的物质如羧甲基纤维素、甲基纤维素和其他纤维素以及淀粉衍生物,聚丙烯酸酯,藻酸盐,明胶,阿拉伯树胶,聚乙烯基吡咯烷酮,聚乙烯醇,甲基乙烯基醚和马来酸酐的共聚物,聚乙二醇,蜡,胶态硅酸或所述物质的混合物。
悬浮液可以口服或局部/经皮给药。它们通过将活性化合物悬浮于悬浮剂中而制备,合适的话加入其他助剂如润湿剂、着色剂、生物吸收促进物质、防腐剂、抗氧化剂、光稳定剂。
液态悬浮剂是所有均相溶剂和溶剂混合物。
合适的润湿剂(分散剂)是上面所给的乳化剂。
可以提到的其他助剂是上述那些。
半固体制剂可以口服或局部/经皮给药。它们与上述悬浮液和乳液的不同仅在于它们具有更高粘度。
为了生产固体制剂,将活性化合物与合适的赋形剂混合,合适的话加入助剂,并且制成所需剂型。
合适的赋形剂是所有生理上耐受的固体惰性物质。所用那些是无机和有机物质。无机物质例如为氯化钠,碳酸盐如碳酸钙,碳酸氢盐,铝氧化物,二氧化钛,硅酸,泥质土,沉淀或胶态二氧化硅或磷酸盐。有机物质例如为糖类、纤维素、食品和饲料如奶粉、动物粉、谷粉和屑、淀粉。
合适的助剂是上面所述的防腐剂、抗氧化剂和/或着色剂。
其他合适的助剂是润滑剂和助滑剂如硬脂酸镁、硬脂酸、滑石、膨润土、崩解促进物质如淀粉或交联的聚乙烯基吡咯烷酮、粘合剂如淀粉、明胶或线性聚乙烯基吡咯烷酮以及干粘合剂如微晶纤维素。
通常而言,“杀寄生虫有效量”是指对生长获得可观察到的效果所需的活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除、破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀寄生虫有效量可以变化。组合物的杀寄生虫有效量也会根据主要条件如所需杀寄生虫效果及持续时间、目标物种、施用方式等而变化。
可以用于本发明的组合物通常可以包含约0.001-95%式I化合物和/或其可接受的盐。
通常有利的是以0.5-100mg/kg/天,优选1-50mg/kg/天的总量施用式I化合物和/或其可接受的盐。
即用制剂以10重量ppm-80重量%,优选0.1-65重量%,更优选1-50重量%,最优选5-40重量%的浓度含有对寄生虫,优选体外寄生虫起作用的式I化合物和/或其可接受的盐。
在使用前稀释的制剂以0.5-90重量%,优选1-50重量%的浓度含有对体外寄生虫起作用的式I化合物和/或其可接受的盐。
此外,制剂以10重量ppm-2重量%,优选0.05-0.9重量%,非常特别优选0.005-0.25重量%的浓度包含对抗体内寄生虫的式I化合物和/或其可接受的盐。
在本发明的优选实施方案中,经皮/局部施用包含式I化合物和/或其可接受的盐的组合物。
在另一优选实施方案中,局部施用以含有化合物的成型制品如套环、挂牌、耳贴、在身体部分上固定用的绑带以及粘合条和箔的形式进行。
通常有利的是施用在三周内以10-300mg/kg,优选20-200mg/kg,最优选25-160mg/kg被处理动物体重的总量释放式I化合物和/或其可接受的盐的固体配制剂。
为了制备成型制品,使用热塑性和柔性塑料以及弹性体和热塑性弹性体。合适的塑料和弹性体是与式I合物充分相容的聚乙烯基树脂、聚氨酯、聚丙烯酸酯、环氧树脂、纤维素、纤维素衍生物、聚酰胺和聚酯。塑料和弹性体的详细列表以及成型制品的制备程序例如在WO 03/086075中给出。
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、杀真菌剂、其他杀虫剂和杀菌剂,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。这些额外成分可以与上述组合物依次或结合使用,合适的话还在紧临使用前加入(桶混物)。例如可以在用其他活性成分处理之前或之后用本发明组合物喷雾植物。
这些试剂可以1∶10-10∶1的重量比与本发明所用试剂混合。将作为杀虫剂使用的式I化合物和/或其可接受的盐或包含它们的组合物与其他农药混合通常导致更宽的杀虫作用谱。
式I化合物和/或其可接受的盐可以与其一起使用且可能产生潜在协同增效效果的下列农药A(下文也称为混合配对A)用来说明可能的组合,但不施加任何限制:
A.1.有机(硫代)磷酸酯类:高灭磷(acephate)、唑啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphos-methyl)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、丙线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、flupyrazophos、噻唑硫磷(fosthiazate)、庚烯磷(heptenophos)、异噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、砜吸磷(oxydemeton-methyl)、一六零五(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、巴胺磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫威(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭磷(vamidothion);
A.2.氨基甲酸酯类:涕灭威(aldicarb)、棉铃威(alanycarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮氧威(butoxycarboxim)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、ethiofoncarb、仲丁威(fenobucarb)、抗螨脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb)、唑蚜威(triazamate);
A.3.合成除虫菊酯类:氟丙菊酯(acrinathrin)、丙烯除虫菊(allethrin)、右旋丙烯菊酯(d-cis-trans allethrin)、右旋反式丙烯菊酯(d-trans allethrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、2-环戊烯基生物烯丙菊酯(bioallethrin S-cyclopentenyl)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、高效氟氯氰菊酯(beta-cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、氯氟氰菊酯(lambda-cyhalothrin)、精高效氯氟氰菊酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、高效反式氯氰菊酯(theta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(tau-fluvalinate)、溴氟醚菊酯(halfenprox)、咪炔菊酯(imiprothrin)、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔酮菊酯(prallethrin)、灭虫菊(resmethrin)、RU 15525、灭虫硅醚(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、ZXI 8901;
A.4.保幼激素模拟物:蒙512(hydroprene)、烯虫炔酯(kinoprene)、蒙五一五(methoprene)、双氧威(fenoxycarb)、蚊蝇醚(pyriproxyfen);
A.5.烟酸受体激动剂/拮抗剂化合物:吡虫清(acetamiprid)、杀虫磺(bensultap)、杀螟丹(cartap hydrochloride)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、烟碱(nicotine)、艾克敌105(spinosad)(别构激动剂)、噻虫啉(thiacloprid)、杀虫环(thiocyclam)、杀虫双(thiosultap-sodium)和AKD1022;
A.6.GABA氯离子通道拮抗剂化合物:氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH(lindane));乙酰虫腈(acetoprole)、乙虫腈(ethiprole)、锐劲特(fipronil)、pyrafluprole、pyriprole、氟吡唑虫(vaniliprole)、式A6.1的苯基吡唑化合物:
A.7.氯离子通道活化剂:齐墩螨素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、米尔螨素(milbemectin)、lepimectin;
A.8.METI I化合物:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、flufenerim、鱼藤酮(rotenone);
A.9.METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
A.10.氧化磷酸化去偶剂:氟唑虫清(chlorfenapyr)、二硝酚(DNOC);
A.11.氧化磷酸化抑制剂:三唑锡(azocyclotin)、三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite)、三氯杀螨砜(tetradifon);
A.12.蜕皮干扰剂:灭蝇胺(cyromazine)、环虫酰肼(chromafenozide)、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide);
A.13.增效剂:增效醚(piperonyl butoxide)、脱叶膦(tribufos);
A.14.钠通道阻断剂化合物:噁二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
A.15.熏蒸剂:溴甲烷(methyl bromide)、氯化苦(chloropicrin)、硫酰氟(sulfuryl fuoride);
A.16.选择性进食阻断剂:crylotie、拒嗪酮(pymetrozine)、氟啶虫酰胺(flonicamid);
A.17.螨生长抑制剂:四螨嗪(clofentezine)、噻螨酮(hexythiazox)、特苯噁唑(etoxazole);
A.18.几丁质合成抑制剂:噻嗪酮(buprofezin)、双三氟虫脲(bistrifluron)、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)、多氟虫酰脲(noviflumuron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);
A.19.类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat);
A.20.章鱼胺能激动剂(octapaminergic agonsits):双甲脒(amitraz);
A.21.Ryanodine受体调节剂:氟虫酰胺(flubendiamide);
A.22.其他各种:磷化铝(aluminium phosphide)、amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、硼砂、溴螨酯(bromopropylate)、氰化物、cyenopyrafen、丁氟螨酯(cyflumetofen)、喹菌酮(chinomethionate)、三氯杀螨醇(dicofol)、氟乙酸酯、膦、啶虫丙醚(pyridalyl)、pyrifluquinazon、硫、有机硫化合物、酒石酸氧锑钾(tartaremetic)以及磺酰亚胺(sulfoximine)化合物A22.1、A22.2或A22.3:
嘧啶基炔基醚化合物A22.4或噻二唑基炔基醚化合物A22.5:
其中RA-22为甲基或乙基且Het*为3,3-二甲基吡咯烷-1-基、3-甲基哌啶-1-基、3,5-二甲基哌啶-1-基、3-三氟甲基哌啶-1-基、六氢氮杂-1-基、2,6-二甲基六氢氮杂-1-基或2,6-二甲基吗啉-4-基;
A.23.N-R′-2,2-二halo-1-R″-环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙或N-R′-2,2-二(R″′)丙酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙,其中R′为甲基或乙基,halo为氯或溴,R″为氢或甲基且R″′为甲基或乙基;
A.24.邻氨基苯甲酰胺(anthranilamides):chloranthraniliprole、式A24.1化合物:
A.25.丙二腈化合物:CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H(2-(2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚基)-2(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-四氟-3-三氟甲基丁基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-九氟己基)-2-(3,3,3-三氟丙基)丙二腈)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-二-(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-九氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-七氟丁基)-2-(2,2,3,3,4,4,5,5-八氟戊基)丙二腈)、CF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(2,2,3,3,3-五氟丙基)丙二腈)、CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,4,4,4-五氟丁基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丁基)丙二腈);
A.26.微生物干扰剂:苏云金芽孢杆菌以色列亚种(Bacillus thuringiensissubsp.Israelensi)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subsp.Aizawai)、Bacillus thuringiensis subsp.Kurstaki、苏云金芽胞杆菌拟步行甲亚种菌株(Bacillus thuringiensis subsp.Tenebrionis)。
A组的市售化合物尤其可以在The Pesticide Manual,第13版,BritishCrop Protection Council(2003)中找到。
式A6.1的硫代酰胺及其制备已经描述于WO 98/28279中。Lepimectin由Agro Project,PJB Publications Ltd,2004年11月已知。Benclothiaz及其制备已经描述于EP-A1 454621中。杀扑磷和对氧磷(Paraoxon)及其制备已经描述于Farm Chemicals Handbook,第88卷,Meister PublishingCompany,2001中。乙酰虫腈及其制备已经描述于WO 98/28277中。氰氟虫胺及其制备已经描述于EP-A1 462 456中。吡氟硫磷(Flupyrazofos)已经描述于Pesticide Science 54,1988,第237-243页和US 4822779中。Pyrafluprole及其制备已经描述于JP 2002193709和WO 01/00614中。Pyriprole及其制备已经描述于WO 98/45274和US 6335357中。Amidoflumet及其制备已经描述于US 6221890和JP 21010907中。Flufenerim及其制备已经描述于WO 03/007717和WO 03/007718中。AKD1022及其制备已经描述于US 6300348中。Chloranthraniliprole已经描述于WO 01/70671、WO 03/015519和WO 05/118552中。式M24.1的邻氨基苯甲酰胺衍生物已经描述于WO 01/70671、WO 04/067528和WO05/118552中。丁氟螨酯及其制备已经描述于WO 04/080180中。氨基喹唑啉酮化合物pyrifluquinazon已经描述于EP A 109 7932中。式M22.1、M22.2或M22.3的磺酰亚胺衍生物或其类似物及其制备已经描述于WO2006/060029中。炔基醚化合物M22.4和M22.5例如描述于JP 2006131529中。有机硫化合物已经描述于WO 2007060839中。丙二腈化合物已经描述于WO 02/089579、WO 02/090320、WO 02/090321、WO 04/006677、WO05/068423、WO 05/068432和WO 05/63694中。
杀真菌混合配对是选自如下的那些:
-酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl);
-胺衍生物,例如4-十二烷基-2,6-二甲基吗啉(aldimorph)、多果定(dodine)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、双胍盐(guazatine)、双胍辛醋酸盐(iminoctadine)、螺噁茂胺(spiroxamin)、克啉菌(tridemorph);
-苯胺基嘧啶类,例如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyrodinyl);
-抗菌素,例如放线菌酮(cycloheximid)、灰黄霉素(griseofulvin)、春雷素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)或链霉素(streptomycin);
-唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、噁醚唑(difenoconazole)、烯唑醇(diniconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquiconazole)、氟硅唑(flusilazole)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、戊唑醇(tebuconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizol)、戊叉唑菌(triticonazole)、粉唑醇(flutriafol);
-二羧酰亚胺类,例如异丙定(iprodion)、甲菌利(myclozolin)、杀菌利(procymidon)、烯菌酮(vinclozolin);
-二硫代氨基甲酸盐类,例如福美铁(ferbam)、代森钠(nabam)、代森锰(maneb)、代森锰锌(mancozeb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福代锌(polycarbamate)、福美双(thiram)、福美锌(ziram)、代森锌(zineb);
-杂环化合物,例如敌菌灵(anilazine)、苯菌灵(benomyl)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、氰霜唑(cyazofamid)、棉隆(dazomet)、二噻农(dithianon)、噁唑酮菌(famoxadon)、咪唑菌酮(fenamidon)、异嘧菌醇(fenarimol)、麦穗宁(fuberidazole)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、稻瘟灵(isoprothiolane)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、啶斑肟(pyrifenox)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、硅噻菌胺(silthiofam)、涕必灵(thiabendazole)、溴氟唑菌(thifluzamid)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)、嗪氨灵(triforine);
-铜杀真菌剂,例如波尔多液(Bordeaux混合物)、乙酸铜、王铜、碱式硫酸铜;
-硝基苯基衍生物,例如如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)、异丙消(nitrophthalisopropyl);
-苯基吡咯类,例如拌种咯(fenpiclonil)或氟噁菌(fludioxonil);
-硫;
-其他杀真菌剂,例如噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、哒菌清(diclomezin)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、克瘟散(edifenphos)、噻唑菌胺(ethaboxam)、环酰菌胺(fenhexamid)、薯瘟锡(fentin-acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、藻菌磷(fosetyl)、乙膦铝(rosetyl-aluminum)、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、苯菌酮(metrafenon)、戊菌隆(pencycuron)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(toloclofos-methyl)、五氯硝基苯(quintozene)、苯酰菌胺(zoxamid);
-嗜球果伞素类(strobilurins)如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)或肟菌酯(trifloxystrobin);
-次磺酸衍生物如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)、对甲抑菌灵(tolylfluanid);
-肉桂酰胺及类似物如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
动物害虫,即节肢动物和线虫,植物、其中植物生长的土壤或水体可以通过本领域已知的任何施用方法与本发明式I化合物和/或其可农用盐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/组合物直接施用于动物害虫或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于动物害虫或植物的场所)。
此外,动物害虫可以通过使目标害虫,其食物供应源、栖息地、繁殖地或其场所与杀虫有效量的式I化合物和/或其可农用盐接触而防治。这里的施用可以在场所、生长中的作物或收获的作物被害虫侵染之前或之后进行。
“场所”是指害虫或寄生虫生长或可能生长的栖息地、繁殖地、植物(尤其是栽培植物)、植物繁殖材料如种子、土壤、区域、材料或环境。
通常而言,“杀虫有效量”是指对生长获得可观察到的效果所需的活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除、破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
式I化合物、其可农用盐及其组合物可以用于保护木质材料如树木、护栏、枕木等,以及建筑物如房子、附属建筑、工厂,还有建筑材料、家具、皮革、纤维、乙烯基制品、电线和电缆等以防蚂蚁和/或白蚁,并防止蚂蚁和白蚁损害作物或人类(例如当害虫侵入房子和公共设施时)。式I化合物不仅施用于周围的土壤表面或地板下的土壤中以保护木质材料,而且还可以施用于堆积制品如地板下混凝土、亭柱、梁、胶合板、家具等的表面,木质制品如碎料板、半包板(halfboard)等以及乙烯基制品如包覆的电线、乙烯基片材,绝热材料如苯乙烯泡沫等。在防止蚂蚁损害作物或人类的施用中,将本发明的蚂蚁防治剂施用于作物或周围土壤,或直接施用于蚂蚁的巢穴等。
本发明化合物还可以预防性地施用于预期出现害虫的地方。
式I化合物和/或其可农用盐还可以通过使生长中的植物与杀虫有效量的式I化合物和/或其可农用盐接触而用于保护生长中的植物免受害虫侵袭或侵染。这里的“接触”包括直接接触(将化合物/组合物直接施用于害虫和/或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于害虫和/或植物的场所)。
在土壤处理或施用于害虫居住地或巢穴的情况下,活性成分(即式I化合物和/或其可农用盐或其与混合配对A的混合物)的量为0.0001-500g/100m2,优选0.001-20g/100m2。
在材料保护中的常规施用率例如为0.01-1000g活性化合物(即式I化合物和/或其可农用盐或其与混合配对A的混合物)/m2被处理材料,理想的是0.1-50g/m2。
用于材料浸渍中的杀虫组合物通常含有0.001-95重量%,优选0.1-45重量%,更优选1-25重量%至少一种驱避剂和/或杀虫剂(即式I化合物和/或其可农用盐或其与混合配对A的混合物)。
为了用于诱饵组合物中,活性成分(即式I化合物和/或其可农用盐或其与混合配对A的混合物)的典型含量为0.001-15重量%,理想的是0.001-5重量%活性化合物。
为了用于喷雾组合物中,活性成分(即式I化合物和/或其可农用盐或其与混合配对A的混合物)的含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
为了用于处理作物植株,本发明活性成分(即式I化合物和/或其可农用盐或其与混合配对A的混合物)的施用率可以为0.1-4000g/ha,理想的是25-600g/ha,更理想的是50-500g/ha。
在种子处理中,本发明化合物或与混合配对A的混合物的施用率通常为0.1g-10kg/100kg植物繁殖材料如种子,优选1g-5kg/100kg种子,尤其是1-200g/100kg植物繁殖材料如种子。
现在通过下列实施例更详细说明本发明。
制备实施例
实施例1:制备1-(3-丙-2-炔基噻唑烷-2-亚基)氨基-1-(2,3-二氯苯基)-2-(3,5-二甲基苯基)乙烷(化合物1)
将1-(4,5-二氢噻唑-2-基)氨基-1-(2,3-二氯苯基)-2-(3,5-二甲基苯基)乙烷(150mg)、碳酸钾(80mg)和二甲基甲酰胺(DMF,10ml)的混合物加热到60℃并加入炔丙基溴(57mg)在DMF(2ml)中的溶液。在相同温度下继续搅拌4小时并在室温下继续搅拌过夜。通过在乙酸乙酯中稀释进行含水后处理、用碳酸钾水溶液(浓度为5%)和水洗涤并在硫酸钠上干燥,得到粗产物,通过在硅胶上的柱层析提纯粗产物,得到13mg标题化合物。
1H-NMR(CDCl3):δ=2.25(s),2.75-3.05(m),3.45(mc),4.25(s),4.65(mc),6.8(mc),7.1-7.55ppm(m)。
实施例2:制备1-{3-[3-(四氢吡喃-2-基氧基)丙基]噻唑烷-2-亚基}氨基-1-(2,3-二氯苯基)-2-(3,5-二甲基苯基)乙烷(化合物2)
在室温下将1-(4,5-二氢噻唑-2-基)氨基-1-(2,3-二氯苯基)-2-(3,5-二甲基苯基)乙烷(300mg)、叔丁醇钾和四氢呋喃(THF,10ml)的混合物用2-(3-溴丙氧基)四氢吡喃(210mg)处理3天。通过在乙酸乙酯中稀释进行含水后处理、用碳酸钾水溶液(浓度为5%)和水洗涤并在硫酸钠上干燥,得到粗产物,通过在硅胶上的柱层析提纯粗产物,得到200mg标题化合物。
1H-NMR(CDCl3):δ=1.45-1.95(m),2.25(s),2.3(d),2.7(mc),3.0(mc),3.35-3.6(m),3.85(mc),4.55-4.7(mc),6.75(s),6.8(s),7.1(t),7.4(mc),7.5ppm(mc)。
实施例3:制备1-(4,5,4′,5′-四氢-[2,3′]联噻唑-2′-亚基)氨基-1-(2,2-二氟苯并[1,3]间二氧杂环戊烯-4-基)-2-(3,5-二甲基苯基)乙烷(化合物3)
在0℃下将1-氨基-1-(2,2-二氟苯并[1,3]间二氧杂环戊烯-4-基)-2-(3,5-二甲基苯基)乙烷(0.39g)在乙醚中的溶液用2-氯乙基异硫氰酸酯(0.16g)处理并在该温度下继续搅拌5小时。将该混合物用氢氧化钠水溶液(1M,4ml)和水(15ml)淬灭并搅拌15分钟。有机相用水洗涤,水相用乙醚萃取,合并的有机相在硫酸钠上干燥并真空除去溶剂。剩余物通过柱层析提纯,得到0.1g标题化合物。
1H-NMR(CDCl3):δ=2.2(s),3.0-3.3(m),4.0(mc),4.2(mc),4.55(mc),6.7(s),6.8(s),6.9(mc),7.05(mc),7.3ppm(mc)。
实施例4:制备2-[1-(2,3-二氯苯基)-2-(3,5-二甲基苯基)乙基亚氨基]噻唑烷-3-硫代甲酸(3-三氟甲基苯基)酰胺(化合物4)
在室温下将1-(4,5-二氢噻唑-2-基)氨基-1-(2,3-二氯苯基)-2-(3,5-二甲基苯基)乙烷(0.25g)在氯仿(10ml)中的溶液用1-异硫氰酸酯基-3-三氟甲基苯(0.13g)处理过夜。真空蒸发溶剂并通过柱层析提纯剩余物,得到0.20g标题化合物。
1H-NMR(CDCl3):δ=2.1(s),2.85-3.2(m),4.55(mc),4.9(mc),5.0(mc),6.65(s),6.8(s),7.1-7.75(m),14.6ppm(s)。
实施例5:制备1-[3-(甲苯-4-磺酰基)噻唑烷-2-亚基]氨基-1-(2,3-二甲基苯基)-2-(3-甲苯基)乙烷(化合物5)
将1-(4,5-二氢-3H-噻唑-2-基)氨基-1-(2,3-二甲基苯基)-2-(3-甲苯基)乙烷(0.20g)在THF(20ml)中的溶液用叔丁醇钾(0.10g)和4-甲基苯磺酰氯(0.14g)处理并将该混合物在室温下搅拌2小时。通过在乙酸乙酯中稀释进行含水后处理、用碳酸钾水溶液(浓度为5%)和水洗涤并在硫酸钠上干燥,得到粗产物,通过在硅胶上的柱层析提纯粗产物,得到0.20g标题化合物。熔点:141.0-144.0℃
类似于前面所示制备实施例制备下表2所示式I′.1化合物(实施例6-21):
表2
对害虫的作用:
I.棉蚜(Aphis gossypii)
通过将侵染的叶片置于试验植株的顶部而将子叶阶段的棉花植株(栽培品种‘Delta Pine’)用约100只实验室培养的蚜虫侵染。24小时后移走所述叶片。将完整植株的子叶浸入试验化合物的梯度溶液中。5天后相对于对照植株上的死亡率测定被处理植株上的蚜虫死亡率。
在该试验中,与未处理对照相比,实施例1-4、6、8-11和13-21的化合物在300ppm下显示出超过70%的死亡率。
II.桃蚜(Myzus persicae)
通过将侵染的叶片置于试验植株的顶部而将第2对叶阶段的辣椒植株(栽培品种为‘California Wonder’)用约40只实验室培养的蚜虫侵染。24小时后移走所述叶片。将完整植株的叶子浸入试验化合物的梯度溶液中。5天后相对于对照植株上的死亡率测定被处理植株上的蚜虫死亡率。
在该试验中,与未处理对照相比,实施例1-4、6-11和13-21的化合物在300ppm下显示出超过70%的死亡率。
III.银叶粉虱
使选取的棉花植株生长到子叶阶段(每盆一株)。将子叶浸入试验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只粉虱成虫(约3-5天龄)。使用抽吸装置和连接于防护移液管头的0.6cm无毒Tygon管(R-3603)收集昆虫。然后将含有收集的昆虫的该管头轻轻地插入含有处理植株的土壤中,使昆虫爬出该管头而到达叶面上取食。将杯子用可反复使用的筛盖(150微米网目的聚酯筛PeCap,购自Tetko Inc)覆盖。将试验植株在保持室中于约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)以防止在杯内截热。在植株处理3天后评价死亡率。
在该试验中,与未处理对照相比,实施例1-4、8-11、13-17和19-21的化合物在300ppm下显示出超过70%的死亡率。
IV.对比例
对比例1:对银叶粉虱的作用
通过在段落III.)中所示的测试评价比较来自制备实施例1和4的本发明化合物对银叶粉虱的作用以及化合物C.3的作用,在化合物C.3中R1为氢(不是按照本发明):
结果汇编在表3中。
表3
Claims (36)
1.式I化合物或其对映体、非对映体或盐:
其中
A为式A.1或A.2的基团:
其中#表示与式I化合物的剩余部分的键,
X选自O、S和NRX,其中
RX选自氢、氰基、硝基、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基、甲酰基、C1-C6烷基羰基和C1-C6烷氧羰基;
R1选自-ORA、-NRB1RB2,
-C(=O)-RC、-C(=O)-ORD、-C(=O)-SRE、-C(=O)-NRB1RB2′、-C(=S)-RC′、-C(=S)-ORD′、-C(=S)-SRE′、-C(=S)-NRB1RB2、-C(=NR1a)-RC′、-C(=NR1b)-ORD′、-C(=NR1c)-SRE′、-C(=NR1d)-NRB1RB2,
-S(=O)-RF、-S(=O)2-RG、-S(=O)2-NRB1RB2′、-P(=O)RH1RH2、-P(=S)RH1RH2,-B-C(=O)-RI、-B-O-C(=O)-RI、-B-S-C(=O)-RI、-B-N(RJ)-C(=O)-RK、-B-C(=S)-RK、-B-O-C(=S)-RK、-B-S-C(=S)-RK、-B-N(RJ)-C(=S)-RK,
C2-C8链烯基、C2-C8炔基、未被取代或可以带有1-4个取代基R1e的C3-C8环烷基,
未被取代或可以带有1-4个取代基R1f的萘基,
未被取代或可以带有1-4个取代基R1g的杂环基,
未被取代或可以带有1-4个取代基R1h的杂芳基,以及
带有选自如下的基团的C1-C6烷基:-NR1iR1j、C1-C4烷氧羰基、C3-C8环烷基、芳基、芳氧基、芳硫基、杂环基、杂环氧基和杂环硫基,其中后提到的八个基团的烷基、环烷基、芳基或杂环基结构部分可以带有1、2、3或4个选自CN、NO2、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基和C3-C8环烷基的基团,其中
B为线性或支化C1-C4亚烷基,其未被取代或可以带有1、2、3或4个选自卤素和C1-C3烷氧基的基团,
RA选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RB1、RB2独立地选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RB2′选自未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RC选自带有1、2、3或4个选自如下的基团的C1-C6烷基:C(=O)OH、芳氧基、杂芳氧基、芳硫基、杂芳硫基或C1-C4烷氧羰基,其中后提到的五个基团未被取代或可以带有1、2、3或4个独立地选自CN、NO2、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基和C3-C8环烷基的基团,
RC′选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RD、RE选自C2-C6链烯基,C2-C6炔基,其中后提到的两个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RD′、RE′、RF、RG、RH1、RH2具有对RD、RE所给的含义之一或选自氢或C1-C6烷基,其未被取代或带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,
RI、RK选自C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
RJ选自氢,C1-C6烷基,C2-C6链烯基,C2-C6炔基,其中后提到的三个基团可以带有1、2、3或4个独立地选自卤素、C1-C3烷氧基、C1-C3卤代烷氧基、C1-C3烷硫基、C1-C3卤代烷硫基和C3-C8环烷基的取代基,未被取代或可以带有1、2、3或4个取代基R1e的C3-C8环烷基,未被取代或可以带有1、2、3或4个取代基R1f的苯基,未被取代或可以带有1、2、3或4个取代基R1f的萘基和未被取代或可以带有1、2、3或4个取代基R1h的杂芳基,
R1a、R1b、R1c和R1d选自氢、C1-C3烷基、C1-C3烷氧基、C3-C8环烷基、C2-C3链烯基和C2-C3链烯氧基,
R1e、R1g相互独立地选自C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基,
R1f、R1h相互独立地选自CN、NO2、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3卤代烷氧基和C3-C8环烷基,
R1i选自氢、C1-C3烷基、C1-C3烷氧基、C3-C8环烷基、C2-C3链烯基和C2-C3链烯氧基,和
R1j选自C1-C3烷基、C1-C3烷氧基、C3-C8环烷基、C2-C3链烯基和C2-C3链烯氧基,和
R2、R3、R4、R5、R6和R7各自独立地为氢、卤素、OH、SH、NH2、SO3H、COOH、氰基、硝基、C1-C6烷基、C1-C6烷氧基、C1-C6烷基氨基、二-C1-C6烷基氨基、C1-C8烷硫基、C2-C6链烯基、C2-C6链烯氧基、C2-C6链烯基氨基、C2-C6链烯硫基、C2-C6炔基、C2-C6炔氧基、C2-C6炔基氨基、C2-C6炔硫基、C1-C6烷基磺酰基、C1-C6烷基次磺酰基、C2-C6链烯基磺酰基、C2-C6炔基磺酰基、甲酰基、C1-C6烷基羰基、C2-C6链烯基羰基、C2-C6炔基羰基、C1-C6烷氧羰基、C2-C6链烯氧羰基、C2-C6炔氧羰基、C1-C6烷基羰氧基、C2-C6链烯基羰氧基、C2-C6炔基羰氧基,其中上述基团的脂族基团中的碳原子可以带有1、2或3个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合,
C(O)NRLRM、(SO2)NRLRM,其中RL和RM各自独立地为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基,其中这些基团中的碳原子可以带有1、2或3个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合,
基团Y-Ar或基团Y-Cy,其中
Y为单键、氧、硫、C1-C6链烷二基或C1-C6链烷二基氧基,
Ar为苯基、萘基或含有1、2、3或4个选自氧、硫和氮的杂原子作为环成员的单环或双环5-10员杂芳族环,其中Ar未被取代或可以带有1、2、3、4或5个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合;和
Cy为C3-C12环烷基,其未被取代或被1、2、3、4或5个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合取代;
并且其中与苯基环的相邻碳原子键合的两个基团R2、R3、R4、R5或R6可以与所述碳原子一起形成稠合苯环、稠合饱和或部分不饱和5、6或7员碳环或稠合5、6或7员杂环,该杂环含有1、2、3或4个选自O、S和N的杂原子作为环成员,并且其中该稠合环未被取代或可以带有1、2、3或4个选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任意组合。
2.根据权利要求1的式I化合物,其中X为S。
3.根据权利要求1或2的式I化合物,其中R1选自-C(=O)-RC、-C(=O)-ORD、-C(=O)-SRE、-C(=O)-NRB1RB2′、-C(=S)-RC′、-C(=S)-ORD′、-C(=S)-SRE′、-C(=S)-NRB1RB2、-C(=NR1e)-RC′、-C(=NR1f)-ORD′、-C(=NR1g)-SRE′、-C(=NR1h)-NRB1RB2,其中RB1、RB2、RB2′、RC、RC′、RD、RD′、RE、RE′、R1e、R1f、R1g和R1h具有前面所给含义之一。
4.根据权利要求3的式I化合物,其中R1为-C(=S)-NRB1RB2,其中RB1和RB2具有前面所给含义之一。
5.根据权利要求1或2的式I化合物,其中R1选自C1-C8链烯基、C1-C8炔基和未被取代或可以带有1-4个如权利要求1所定义的取代基R1e的C3-C8环烷基。
6.根据权利要求1或2的式I化合物,其中R1选自-S(=O)-RF、-S(=O)2-RG、-S(=O)2-NRB1RB2′、-P(=O)RH1RH2、-P(=S)RH1RH2,其中RB1、RB2、RF、RG、RH1和RH2具有权利要求1所给含义之一。
7.根据前述权利要求中任一项的式I化合物,其中A为如权利要求1所定义的式A.1的基团。
8.根据前述权利要求中任一项的式I化合物,其中R2选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。
9.根据权利要求1-7中任一项的式I化合物,其中R2与R3一起形成选自-O-CH2-O-、-O-CH2-CH2-或-O-CF2-O-的二价基团。
10.根据权利要求1-8中任一项的式I化合物,其中R3选自氢、卤素、C1-C3烷基和C1-C3卤代烷基。
11.根据前述权利要求中任一项的式I化合物,其中R4选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。
12.根据前述权利要求中任一项的式I化合物,其中R5选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。
13.根据前述权利要求中任一项的式I化合物,其中R6选自卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。
14.根据前述权利要求中任一项的式I化合物,其中R7选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。
16.根据权利要求15的式I化合物或其对映体、非对映体或盐,其中
R2选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基;
R3选自氢、卤素、C1-C3烷基和C1-C3卤代烷基;或
R2与R3一起形成选自-O-CH2-CH2-、-O-CH2-O-或-O-CF2-O-的二价基团;
R4选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基;
R5选自氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基;和
R6选自卤素、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基和C1-C3卤代烷氧基。
17.根据权利要求15或16的式I化合物,其中A为如权利要求1所定义的式A.1的基团。
18.根据权利要求15-17中任一项的式I化合物,其中X为S。
19.根据权利要求15-18中任一项的式I化合物,其中R1选自-C(=O)-RC、-C(=O)-ORD、-C(=O)-SRE、-C(=O)-NRB1RB′、-C(=S)-RC′、-C(=S)-ORD′、-C(=S)-SRE′、-C(=S)-NRB1RB2、-C(=NR1e)-RC′、-C(=NR1f)-ORD′、-C(=NR1g)-SRE′、-C(=NR1h)-NRB1RB2,其中RB1、RB2、RB2′、RC、RC′、RD、RD′、Re、RE′、R1e、NR1f、R1g和R1h具有前面所给含义之一。
20.根据权利要求19的式I化合物,其中R1为-C(=S)-NRB1RB2,其中RB1和RB2具有前面所给含义之一。
21.根据权利要求15-18中任一项的式I化合物,其中R1选自C1-C8链烯基、C1-C8炔基和未被取代或可以带有1-4个如权利要求1所定义的取代基R1e的C3-C8环烷基。
22.根据权利要求15-18中任一项的式I化合物,其中R1选自-S(=O)-RF、-S(=O)2-RG、-S(=O)2-NRB1RB2′、-P(=O)RH1RH2、-P(=S)RH1RH2,其中RB1、RB2、RF、RG、RH1和RH2具有权利要求1所给含义之一。
23.根据权利要求15-22中任一项的式I化合物,其中R2选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
24.根据前述权利要求中任一项的式I化合物,其中R2和R3具有前面所给的不为氢的含义之一。
25.根据前述权利要求中任一项的式I化合物,其中R2和R4具有前面所给的不为氢的含义之一。
26.根据前述权利要求中任一项的式I化合物,其中R5选自氢、氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
27.根据前述权利要求中任一项的式I化合物,其中R6选自氟、氯、溴、甲基、甲氧基、二氟甲基、三氟甲基、二氟甲氧基和三氟甲氧基。
28.根据前述权利要求中任一项的式I化合物或其盐在防治动物害虫中的用途。
29.如权利要求28所要求的用途,用于防治节肢动物害虫和/或线虫。
30.如权利要求29所要求的用途,用于防治昆虫。
31.如权利要求29所要求的用途,用于防治螨科(acaridae)。
32.一种农用组合物,含有至少一种如权利要求1-27中任一项所定义的式I化合物和/或其可农用盐以及至少一种液体或固体载体。
33.一种防治动物害虫的方法,该方法包括用杀虫有效量的如权利要求1-27中任一项所定义的式I化合物或其盐或杀虫有效量的如权利要求32所定义的农用组合物处理害虫、其食物供应源、其栖息地或其繁殖地或其中害虫生长或可能生长的植物、植物繁殖材料、土壤、区域、材料或环境或者要防止害虫侵袭或侵染的材料、植物、植物繁殖材料、土壤、表面或空间。
34.如权利要求33所要求的方法,用于保护植物繁殖材料和/或由其生长的植物,该方法包括用杀虫有效量的如权利要求1-27中任一项所定义的式I化合物或其可农用盐或杀虫有效量的如权利要求32所定义的农用组合物处理植物繁殖材料。
35.植物繁殖材料,包含至少一种如权利要求1-27中任一项所定义的式I化合物和/或其可农用盐。
36.一种处理或保护动物以防寄生虫侵袭或侵染的方法,包括使动物与杀寄生虫有效量的如权利要求1-27中任一项所定义的式I化合物或其可兽用盐接触。
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US7652023B2 (en) | 2005-11-23 | 2010-01-26 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
JP2009520746A (ja) | 2005-12-22 | 2009-05-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺虫組成物 |
KR20090024301A (ko) | 2006-06-30 | 2009-03-06 | 바스프 에스이 | 치환된 1-(아졸린-2-일)-아미노-2-아릴-1-헤타릴-에탄 화합물 |
JP5511393B2 (ja) * | 2007-03-01 | 2014-06-04 | ビーエーエスエフ ソシエタス・ヨーロピア | アミノチアゾリン化合物を含む殺有害生物活性混合物 |
-
2008
- 2008-07-02 AU AU2008270332A patent/AU2008270332B2/en not_active Expired - Fee Related
- 2008-07-02 ES ES08774651T patent/ES2432846T3/es active Active
- 2008-07-02 JP JP2010513979A patent/JP5518701B2/ja not_active Expired - Fee Related
- 2008-07-02 CN CN200880023200A patent/CN101687813A/zh active Pending
- 2008-07-02 EP EP08774651.7A patent/EP2176232B1/en active Active
- 2008-07-02 TW TW097124925A patent/TW200909421A/zh unknown
- 2008-07-02 WO PCT/EP2008/058517 patent/WO2009004032A1/en active Application Filing
- 2008-07-02 MX MX2009013764A patent/MX2009013764A/es not_active Application Discontinuation
- 2008-07-02 BR BRPI0813488-0A2A patent/BRPI0813488A2/pt not_active IP Right Cessation
- 2008-07-02 KR KR1020107002380A patent/KR20100040312A/ko not_active Application Discontinuation
- 2008-07-02 US US12/667,299 patent/US8211924B2/en not_active Expired - Fee Related
- 2008-07-02 RU RU2010103325/04A patent/RU2010103325A/ru not_active Application Discontinuation
- 2008-07-02 CA CA002691573A patent/CA2691573A1/en not_active Abandoned
- 2008-07-03 UY UY31206A patent/UY31206A1/es unknown
- 2008-07-03 AR ARP080102890A patent/AR066159A1/es not_active Application Discontinuation
- 2008-07-03 CL CL2008001976A patent/CL2008001976A1/es unknown
- 2008-07-03 PE PE2008001127A patent/PE20090737A1/es not_active Application Discontinuation
-
2009
- 2009-12-10 IL IL202658A patent/IL202658A0/en unknown
- 2009-12-15 CR CR11166A patent/CR11166A/es not_active Application Discontinuation
- 2009-12-24 MA MA32449A patent/MA31463B1/fr unknown
-
2010
- 2010-01-06 EC EC2010009853A patent/ECSP109853A/es unknown
- 2010-02-01 ZA ZA2010/00732A patent/ZA201000732B/en unknown
Also Published As
Publication number | Publication date |
---|---|
ZA201000732B (en) | 2011-04-28 |
EP2176232A1 (en) | 2010-04-21 |
US20100280078A1 (en) | 2010-11-04 |
AU2008270332B2 (en) | 2012-11-15 |
JP5518701B2 (ja) | 2014-06-11 |
RU2010103325A (ru) | 2011-08-10 |
UY31206A1 (es) | 2009-01-30 |
ES2432846T3 (es) | 2013-12-05 |
CL2008001976A1 (es) | 2009-09-25 |
EP2176232B1 (en) | 2013-06-19 |
WO2009004032A1 (en) | 2009-01-08 |
ECSP109853A (es) | 2010-02-26 |
IL202658A0 (en) | 2010-06-30 |
JP2010531853A (ja) | 2010-09-30 |
MA31463B1 (fr) | 2010-06-01 |
MX2009013764A (es) | 2010-01-26 |
US8211924B2 (en) | 2012-07-03 |
TW200909421A (en) | 2009-03-01 |
CA2691573A1 (en) | 2009-01-08 |
AR066159A1 (es) | 2009-07-29 |
KR20100040312A (ko) | 2010-04-19 |
CR11166A (es) | 2010-04-21 |
PE20090737A1 (es) | 2009-07-23 |
BRPI0813488A2 (pt) | 2015-01-06 |
AU2008270332A1 (en) | 2009-01-08 |
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