CN100572367C - 用于防治昆虫、蜘蛛和线虫的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物 - Google Patents
用于防治昆虫、蜘蛛和线虫的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物 Download PDFInfo
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- CN100572367C CN100572367C CNB2004800389090A CN200480038909A CN100572367C CN 100572367 C CN100572367 C CN 100572367C CN B2004800389090 A CNB2004800389090 A CN B2004800389090A CN 200480038909 A CN200480038909 A CN 200480038909A CN 100572367 C CN100572367 C CN 100572367C
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- 238000000605 extraction Methods 0.000 description 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003667 hormone antagonist Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
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- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
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- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 229920002114 octoxynol-9 Polymers 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000005880 oxathiolanyl group Chemical group 0.000 description 1
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- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000006170 pentacyclic group Chemical group 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229950001664 phoxim Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
Classifications
-
- 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
- A01N43/72—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
本发明涉及通式(I)的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐,其中A为式A1或A2的基团,其中m为0、1、2、3、4或5,n为0、1、2、3、4或5,X为硫或氧且其中变量R1、R2、R3、R4、R5a、R5b、R5c、R5d如权利要求书中所定义。本发明还涉及一种防治选自昆虫、蜘蛛和线虫的动物害虫的方法以及一种保护作物免受昆虫、蜘蛛或线虫侵袭或侵染的方法,包括使作物与杀虫有效量的通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其盐接触。
Description
本发明涉及可以用于防治昆虫、蜘蛛和线虫的1-(唑啉-2-基)氨基-1,2-二苯基乙烷(1-(azolin-2-yl)amino-1,2-diphenylethane)化合物。本发明还涉及防治选自昆虫、蜘蛛和线虫的动物害虫的方法以及用于防治动物害虫的农业组合物。
动物害虫,尤其是昆虫、蜘蛛和线虫破坏生长作物和收获的作物并且侵袭木质住宅和商业建筑,对食品供应和财产造成大的经济损失。尽管已知许多杀虫试剂,但由于目标害虫能够对所述试剂产生耐受性,因此仍然需要防治昆虫、蜘蛛和线虫的新试剂。
Jennings等在Pesticide Biochemistryand Physiology 30,1988,第190-197页中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,这些化合物在活性或活性谱的宽度上是有限的。
因此,本发明的目的是提供具有良好的杀虫活性且对大量不同动物害虫,尤其是难以防治的昆虫、蜘蛛和线虫的具有宽活性谱的化合物。
已经发现这些目的可以通过通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物及式I化合物的可农用盐实现:
其中A为式A1或A2的基团:
以及其中
m为0、1、2、3、4或5;
n为0、1、2、3、4或5;
X为硫或氧;
R1、R2各自独立地为卤素、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烷基次硫酰基(alkylsulfoxyl)、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(=HC(O)-或甲酰氧基)、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个基团R#的任何组合,
C(O)NRaRb、(SO2)NRaRb,其中Ra和Rb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个基团R#的任何组合,
基团Y-Ar或基团Y-Cy,其中
Y为单键、氧、硫、C1-C6亚烷基或C1-C6亚烷基氧基,
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5-10元单环或双环杂芳族环,其中Ar未被取代或可以带有1、2、3、4或5个基团R#的任何组合;和
Cy为C3-C12环烷基,该基团未被取代或被1、2、3、4或5个基团R#的任何组合取代;
以及其中与苯基环的相邻碳原子键合的两个基团R1或两个基团R2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元碳环或含有1、2、3或4个选自氧、硫和氮的杂原子作为环成员的稠合5、6或7元杂环,且其中该稠合环未被取代或可以带有1、2、3或4个基团R#的任何组合;
R3、R4各自独立地为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基,其中这些基团中的碳原子可以带有1、2或3个基团R#的任何组合,苯基或苄基,其各自未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代;
R5a、R5b、R5c、R5d各自独立地为氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基氨基、C1-C6烷氧基、C3-C6环烷基,其中这些基团中的碳原子可以带有1、2或3个基团R#、卤素、氰基、硝基、羟基、巯基、氨基的任何组合,
苯基或苄基,其各自未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代;
R6为氢、氰基、硝基、C1-C6烷基、甲酰基、C1-C6烷基羰基、C1-C6烷氧羰基、C1-C6烷硫基羰基,其中上述基团的脂族基团中的碳原子可以带有1、2或3个基团R#的任何组合,
C(O)NRaRb或(SO2)NRaRb,其中Ra和Rb如上所定义,苯基、苯氧基或苄基,3个后提及的基团各自可以未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代;
R7为氢、氰基、硝基、C1-C6烷基、甲酰基、C1-C6烷基羰基、C1-C6烷氧羰基、C1-C6烷硫基羰基,其中上述基团的脂族基团中的碳原子可以带有1、2或3个基团R#的任何组合,
C(O)NRaRb或(SO2)NRaRb,其中Ra和Rb如上所定义,苯基、苯氧基或苄基,3个后提及的基团各自可以未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代;和
R#为卤素、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卤代烷氧基或C1-C6烷硫基。
因此,本发明涉及通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐。这些化合物具有高杀虫活性且对宽范围的选自昆虫、蜘蛛和线虫的动物害虫具有活性。
因此,本发明还涉及一种防治选自昆虫、蜘蛛和线虫的动物害虫的方法,包括使动物害虫,其栖息地,繁殖地,食物源,动物害虫在其中生长或可能生长的植物、种子、土壤、区域、材料或环境或需要保护以免受昆虫、蜘蛛或线虫侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其可农用盐接触。
此外,本发明提供了一种保护作物免受昆虫、蜘蛛或线虫侵袭或侵染的方法,包括使作物与杀虫有效量的通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其盐接触。
此外,本发明涉及农业组合物,优选呈可直接喷雾溶液、乳液、糊、油分散体、粉末、撒播用材料、粉剂或颗粒形式,其包含至少一种如上所定义的通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物或其盐以及与之混合的一种或多种可农用惰性固体或液体载体和需要的话,至少一种表面活性剂。
通式I的化合物可能具有一个或多个手性中心,此时它们以对映体或非对映体的混合物存在。本发明提供了纯对映体或非对映体或其混合物。通式I的化合物还可以不同互变异构体形式存在。本发明包括单个互变异构体(若可分离的话)以及互变异构体混合物。
式I化合物的盐尤其是可农用盐。它们可以常规方法形成,例如若式I化合物具有碱性官能度,则通过使该化合物与所述阴离子的酸反应,或通过使式I的酸性化合物与合适碱反应。
合适的可农用盐尤其是其阳离子和阴离子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的离子,优选锂离子、钠离子和钾离子,碱土金属的离子,优选钙离子、镁离子和钡离子,以及过渡金属的离子,优选锰离子、铜离子、锌离子和铁离子,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)锍以及氧化锍离子,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、硫酸氢根离子、硫酸根离子、磷酸二氢根离子、磷酸氢根离子、磷酸根离子、硝酸根离子、碳酸氢根离子、碳酸根离子、六氟硅酸根离子、六氟磷酸根离子、苯甲酸根离子和C1-C4链烷酸的阴离子,优选甲酸根离子、乙酸根离子、丙酸根离子和丁酸根离子。它们可以通过使式Ia和Ib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。
在变量的上述定义中提到的有机结构部分象术语卤素一样是各基团成员的单独列举的集合性术语。前缀Cn-Cm在每种情况下表示基团中的可能碳原子数。
术语卤素在每种情况下表示氟、溴、氯或碘,尤其是氟、氯或溴。
其他含义的实例是:
本文所用术语“C1-C6烷基”以及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烷基次硫酰基、C1-C6烷基羰基、C1-C6烷氧羰基、C1-C6烷硫基羰基和C1-C6烷基羰氧基的烷基部分指具有1-6个碳原子,尤其是1-4个碳原子的饱和直链或支化烃基,例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、庚基、辛基、2-乙基己基、壬基和癸基及其异构体。C1-C4烷基例如指甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基或1,1-二甲基乙基。
在各烷基中,碳原子可以带有1、2或3个基团R#。换言之,这些基团中的氢原子各自可以相互独立地被上述基团R#之一替换。在R#为卤素的情况下,所述烷基中的1、2、3个或所有氢原子通常被卤素,尤其是氟或氯替换。这些基团也称为卤代烷基。在R#为氰基、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卤代烷氧基或C1-C6烷硫基的情况下,所述烷基中的1或2个氢原子通常可以被基团R#替换。
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),其中这些基团中的一些或所有氢原子可以被上述卤原子替换,例如C1-C4卤代烷基如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、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。
本文所用术语“C1-C6烷氧基”指经由氧原子连接的具有1-6个碳原子的直链或支化饱和烷基(如上所述)。实例包括C1-C6烷氧基如甲氧基、乙氧基、OCH2-C2H5、OCH(CH3)2、正丁氧基、OCH(CH3)-C2H5、OCH2-CH(CH3)2、OC(CH3)3、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”指其中氢原子被氟、氯、溴和/或碘部分或完全取代的上述C1-C6烷氧基,即例如C1-C6卤代烷氧基如氯甲氧基、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、二氯氟甲氧基、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、1-(溴甲基)-2-溴乙氧基、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-己氧基或十二氟己氧基,尤其是氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、2-氟乙氧基、2-氯乙氧基或2,2,2-三氟乙氧基。
本文所用术语“C1-C6烷氧基-C1-C6烷基”指其中1个碳原子带有上述C1-C6烷氧基的C1-C6烷基。实例是CH2-OCH3、CH2-OC2H5、正丙氧基甲基、CH2-OCH(CH3)2、正丁氧基甲基、(1-甲基丙氧基)甲基、(2-甲基丙氧基)甲基、CH2-OC(CH3)3、2-(甲氧基)乙基、2-(乙氧基)乙基、2-(正丙氧基)乙基、2-(1-甲基乙氧基)乙基、2-(正丁氧基)乙基、2-(1-甲基丙氧基)乙基、2-(2-甲基丙氧基)乙基、2-(1,1-二甲基乙氧基)乙基、2-(甲氧基)丙基、2-(乙氧基)丙基、2-(正丙氧基)丙基、2-(1-甲基乙氧基)丙基、2-(正丁氧基)丙基、2-(1-甲基丙氧基)丙基、2-(2-甲基丙氧基)丙基、2-(1,1-二甲基乙氧基)丙基、3-(甲氧基)丙基、3-(乙氧基)丙基、3-(正丙氧基)丙基、3-(1-甲基乙氧基)丙基、3-(正丁氧基)丙基、3-(1-甲基丙氧基)丙基、3-(2-甲基丙氧基)丙基、3-(1,1-二甲基乙氧基)丙基、2-(甲氧基)丁基、2-(乙氧基)丁基、2-(正丙氧基)丁基、2-(1-甲基乙氧基)丁基、2-(正丁氧基)丁基、2-(1-甲基丙氧基)丁基、2-(2-甲基丙氧基)丁基、2-(1,1-二甲基乙氧基)丁基、3-(甲氧基)丁基、3-(乙氧基)丁基、3-(正丙氧基)丁基、3-(1-甲基乙氧基)丁基、3-(正丁氧基)丁基、3-(1-甲基丙氧基)丁基、3-(2-甲基丙氧基)丁基、3-(1,1-二甲基乙氧基)丁基、4-(甲氧基)丁基、4-(乙氧基)丁基、4-(正丙氧基)丁基、4-(1-甲基乙氧基)丁基、4-(正丁氧基)丁基、4-(1-甲基丙氧基)丁基、4-(2-甲基丙氧基)丁基、4-(1,1-二甲基乙氧基)丁基等。
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的任何键处键合的具有1-6个碳原子的直链或支化饱和烷基(如上所述)。实例包括C1-C6烷基羰基如CO-CH3、CO-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、1,1-二甲基乙基羰基、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个碳原子的直链或支化烷氧基(如上所述)。实例包括(C1-C6烷氧基)羰基,例如CO-OCH3、CO-OC2H5、COO-CH2-C2H5、CO-OCH(CH3)2、正丁氧羰基、CO-OCH(CH3)-C2H5、CO-OCH2-CH(CH3)2、CO-OC(CH3)3、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-甲基丙氧基羰基或1-乙基-2-甲基丙氧基羰基。
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的任何键处键合的具有1-6个碳原子的直链或支化饱和烷基(如上所述)。实例包括C1-C6烷基羰氧基如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、1,1-二甲基乙基羰氧基、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、1,2-二甲基丙基羰氧基等。
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个碳原子的直链或支化饱和烷基(如上所述),例如C1-C4烷硫基如甲硫基、乙硫基、丙硫基、1-甲基乙硫基、丁硫基、1-甲基丙硫基、2-甲基丙硫基、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-甲基丙硫基或1-乙基-2-甲基丙硫基。
本文所用术语“C1-C6烷硫基羰基”指经由羰基碳原子连接的具有1-6个碳原子的直链或支化烷硫基(如上所述)。实例包括CO-SCH3、CO-SC2H5、CO-SCH2-C2H5、CO-SCH(CH3)2、正丁硫基羰基、CO-SCH(CH3)-C2H5、CO-SCH2-CH(CH3)2、CO-SC(CH3)3、正戊硫基羰基、1-甲基丁硫基羰基、2-甲基丁硫基羰基、3-甲基丁硫基羰基、2,2-二甲基丙硫基羰基、1-乙基丙硫基羰基、正己硫基羰基、1,1-二甲基丙硫基羰基、1,2-二甲基丙硫基羰基、1-甲基戊硫基羰基、2-甲基戊硫基羰基、3-甲基戊硫基羰基、4-甲基戊硫基羰基、1,1-二甲基丁硫基羰基、1,2-二甲基丁硫基羰基、1,3-二甲基丁硫基羰基、2,2-二甲基丁硫基羰基、2,3-二甲基丁硫基羰基、3,3-二甲基丁硫基羰基、1-乙基丁硫基羰基、2-乙基丁硫基羰基、1,1,2-三甲基丙硫基羰基、1,2,2-三甲基丙硫基羰基、1-乙基-1-甲基丙硫基羰基或1-乙基-2-甲基丙硫基羰基。
本文所用术语“C1-C6烷基亚磺酰基”(C1-C6烷基次硫酰基:C1-C6烷基-S(=O)-)指通过亚磺酰基的硫原子在烷基中的任何键处键合的具有1-6个碳原子的直链或支化饱和烃基(如上所述)。实例包括C1-C6烷基亚磺酰基:SO-CH3、SO-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、1,1-二甲基乙基亚磺酰基、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-甲基丙基亚磺酰基或1-乙基-2-甲基丙基亚磺酰基。
术语“C1-C6烷基氨基”指带有一个上述烷基的仲氨基,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、1-乙基-2-甲基丙基氨基。
术语“二(C1-C6烷基)氨基”指带有两个上述烷基的叔氨基,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、N-(正戊基)-N-乙基氨基等。
本文所用术语“C1-C6烷基磺酰基”(C1-C6烷基-S(=O)2-)指经由磺酰基的硫原子在烷基中的任何键处键合的具有1-6个碳原子的直链或支化饱和烷基(如上所述)。实例包括C1-C6烷基磺酰基如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、SO2-C(CH3)3、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-甲基丙基磺酰基或1-乙基-2-甲基丙基磺酰基等。
本文所用术语“C2-C6链烯基”以及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部分指具有2-6个碳原子和在任何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。
在各链烯基中,碳原子可以带有1、2或3个基团R#。换言之,这些基团中的氢原子各自可以相互独立地被上述基团R#之一替换。在R#为卤素的情况下,所述烷基中的1、2、3个或所有氢原子通常被卤素,尤其是氟或氯替换。这些基团也称为卤代烷基。在R#为氰基、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卤代烷氧基或C1-C6烷硫基的情况下,所述烷基中的1或2个氢原子通常可以被基团R#替换。
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链烯基氨基”指经由氮原子连接的具有2-6个碳原子的直链或支化链烯基(如上所述),例如乙烯氨基、烯丙氨基(丙烯-3-基氨基)、甲代烯丙氨基、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。
本文所用术语“C2-C6炔基”以及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C1-C6炔基羰氧基的炔基部分指具有2-10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。
在各炔基中,碳原子可以带有1、2或3个基团R#。换言之,这些基团中的氢原子各自可以相互独立地被上述基团R#之一替换。在R#为卤素的情况下,所述烷基中的1、2、3个或所有氢原子通常被卤素,尤其是氟或氯替换。这些基团也称为卤代烷基。在R#为氰基、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卤代烷氧基或C1-C6烷硫基的情况下,所述烷基中的1或2个氢原子通常可以被基团R#替换。
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炔基氨基”指经由氮原子连接的具有2-6个碳原子的直链或支化炔基(如上所述),例如炔丙氨基(丙炔-3-基氨基)、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,尤其是3-6个碳原子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、环壬基或环癸基。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]壬基。三环基团的实例是金刚烷基和高金刚烷基。
各环烷基可以带有1、2、3、4或5个上述基团R#。换言之,这些基团中的1、2、3、4或5个氢原子可以相互独立地被上述基团R#之一替换。环烷基上的优选基团R#选自卤素,尤其是氟或氯,以及C1-C6烷基。
本文所用术语“单环或双环杂芳族环”指具有5或6个环成员的单环杂芳族基团,该基团可以包含稠合的5、6或7元环且因此环成员总数为8-10,其中在每种情况下这些环成员中的1、2、3或4个为相互独立地选自氧、氮和硫的杂原子。杂环基团可以经由碳环成员或经由氮环成员连接于该分子的其余部分。稠合环包含C5-C7环烷基、C5-C7环烯基或5-7元杂环基和苯基。
单环5-6元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。
带有稠合苯基环的5-6元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、苯并噁唑基和苯并咪唑基。带有稠合环烯基环的5-6元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“5-7元杂环基”包括上述单环杂芳族环和具有5、6或7个环成员的非芳族饱和或部分不饱和杂环。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、吡唑烷基、咪唑烷基、四氢呋喃基、二氢呋喃基、1,3-二氧戊环基、间二氧杂环戊烯基(dioxolenyl)、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、二噁烷基、噻喃基、二氢噻喃基、四氢噻喃基、吗啉基、噻嗪基等。
考虑到通式I化合物的杀虫活性,优选如下式I化合物,其中变量n、m、R1、R2、R3、R4、R5a、R5b、R5c、R5d、R6和R7相互独立地或更优选组合具有下列含义。
n为0、1或2;
m为0、1或2;
m+n=0、1、2、3或4,尤其是1、2、3或4;
R1为卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和苯基,该苯基未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代,尤其是氟、氯、溴、甲基、乙基、甲氧基、乙氧基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、甲硫基或苯基,该苯基未被取代或可以带有1、2或3个选自卤素或甲基的基团;
R2为卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和苯基,该苯基未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代,尤其是氟、氯、溴、甲基、乙基、甲氧基、乙氧基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、甲硫基或苯基,该苯基未被取代或可以带有1、2或3个选自卤素或甲基的基团;
R3为氢或C1-C4烷基,尤其是氢或甲基,最优选氢;
R4为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基或苯基,该苯基未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代;
R5a、R5b、R5c和R5d各自为氢或这些基团中的一个还可以为C1-C4烷基;
R6为氢、C1-C4烷基、甲酰基、C1-C6烷基羰基、C1-C4卤代烷基羰基、C1-C6烷氧羰基、C1-C4烷氧基-C1-C4烷氧羰基或C1-C6烷硫基羰基;
R7为氢。
在本发明的非常优选实施方案中,基团R3和R4均为氢。在本发明的另一优选实施方案中,R3为氢且R4选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基或苯基,该苯基未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代。在该实施方案中,R4优选为甲基、乙基或尤其是未取代或取代的苯基。
本发明的另一实施方案涉及其中基团R5a、R5b、R5c和R5d中的至少一个且优选1个或2个不为氢的式I化合物。此时优选其中基团R5a、R5b、R5c或R5d中的1个或2个选自烷基、任选取代的苯基或任选取代的苄基的式I化合物。
在化合物I中,优选其中A为式A2的基团的那些,尤其是其中A为A2的式I化合物,其中R7为H。这些化合物是其中A为A1的式I化合物的互变异构体,其中R6为氢。这些互变异构体作为其平衡混合物存在。
在式I化合物中,优选下列式I-A化合物,其中A为基团A2,其中X为O:
其中变量n、m、R1和R2具有上面所给的含义。这些化合物的实例是其中(R1)n和(R2)m具有表A的每一行中所给含义的那些(化合物I-A.1至I-A.1347)。在表A中,基团前面的数字表示其在苯基环上的位置。
表A:
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1 | - | - |
A-2 | 2-Cl | - |
A-3 | 2-F | - |
A-4 | 2-Br | - |
A-5 | 2-OCH<sub>3</sub> | - |
A-6 | 2-CF<sub>3</sub> | - |
A-7 | 2-C<sub>6</sub>H<sub>5</sub> | - |
A-8 | 2-CH<sub>3</sub> | - |
A-9 | 3-Cl | - |
A-10 | 3-F | - |
A-11 | 3-Br | - |
A-12 | 3-OCH<sub>3</sub> | - |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-13 | 3-CF<sub>3</sub> | - |
A-14 | 3-C<sub>6</sub>H<sub>5</sub> | - |
A-15 | 3-CH<sub>3</sub> | - |
A-16 | 4-Cl | - |
A-17 | 4-F | - |
A-18 | 4-Br | - |
A-19 | 4-OCH<sub>3</sub> | - |
A-20 | 4-CF<sub>3</sub> | - |
A-21 | 4-C<sub>6</sub>H<sub>5</sub> | - |
A-22 | 4-CH<sub>3</sub> | - |
A-23 | 2-Cl,6-Cl | - |
A-24 | 2-Cl,5-Cl | - |
A-25 | 2-Cl,3-Cl | - |
A-26 | 2-Cl,4-Cl | - |
A-27 | 3-Cl,4-Cl | - |
A-28 | 3-Cl,5-Cl | - |
A-29 | 2-F,6-F | - |
A-30 | 2-F,5-F | - |
A-31 | 2-F,3-F | - |
A-32 | 2-F,4-F | - |
A-33 | 3-F,4-F | - |
A-34 | 3-F,5-F | - |
A-35 | 2-F,6-Cl | - |
A-36 | 2-F,5-Cl | - |
A-37 | 2-F,3-Cl | - |
A-38 | 2-F,4-Cl | - |
A-39 | 3-F,4-Cl | - |
A-40 | 3-F,5-Cl | - |
A-41 | 2-Cl,6-F | - |
A-42 | 2-Cl,5-F | - |
A-43 | 2-Cl,3-F | - |
A-44 | 2-Cl,4-F | - |
A-45 | 3-Cl,4-F | - |
A-46 | 3-OCH<sub>3</sub>,5-Cl | - |
A-47 | 3-OCH<sub>3</sub>,4-Cl | - |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-48 | 3-OCH<sub>3</sub>,2-Cl | - |
A-49 | 4-OCH<sub>3</sub>,3-Cl | - |
A-50 | 4-OCH<sub>3</sub>,2-Cl | - |
A-51 | 2-OCH<sub>3</sub>,3-Cl | - |
A-52 | 2-OCH<sub>3</sub>,4-Cl | - |
A-53 | 2-OCH<sub>3</sub>,5-Cl | - |
A-54 | 2-OCH<sub>3</sub>,6-Cl | - |
A-55 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | - |
A-56 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | - |
A-57 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | - |
A-58 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | - |
A-59 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | - |
A-60 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | - |
A-61 | 2-Cl | 2-Cl |
A-62 | 2-F | 2-Cl |
A-63 | 2-Br | 2-Cl |
A-64 | 2-OCH<sub>3</sub> | 2-Cl |
A-65 | 2-CF<sub>3</sub> | 2-Cl |
A-66 | 2-C<sub>6</sub>H<sub>5</sub> | 2-Cl |
A-67 | 2-CH<sub>3</sub> | 2-Cl |
A-68 | 3-Cl | 2-Cl |
A-69 | 3-F | 2-Cl |
A-70 | 3-Br | 2-Cl |
A-71 | 3-OCH<sub>3</sub> | 2-Cl |
A-72 | 3-CF<sub>3</sub> | 2-Cl |
A-73 | 3-C<sub>6</sub>H<sub>5</sub> | 2-Cl |
A-74 | 3-CH<sub>3</sub> | 2-Cl |
A-75 | 4-Cl | 2-Cl |
A-76 | 4-F | 2-Cl |
A-77 | 4-Br | 2-Cl |
A-78 | 4-OCH<sub>3</sub> | 2-Cl |
A-79 | 4-CF<sub>3</sub> | 2-Cl |
A-80 | 4-C<sub>6</sub>H<sub>5</sub> | 2-Cl |
A-81 | 4-CH<sub>3</sub> | 2-Cl |
A-82 | 2-Cl,6-Cl | 2-Cl |
A-83 | 2-Cl,5-Cl | 2-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-84 | 2-Cl,3-Cl | 2-Cl |
A-85 | 2-Cl,4-Cl | 2-Cl |
A-86 | 3-Cl,4-Cl | 2-Cl |
A-87 | 3-Cl,5-Cl | 2-Cl |
A-88 | 2-F,6-F | 2-Cl |
A-89 | 2-F,5-F | 2-Cl |
A-90 | 2-F,3-F | 2-Cl |
A-91 | 2-F,4-F | 2-Cl |
A-92 | 3-F,4-F | 2-Cl |
A-93 | 3-F,5-F | 2-Cl |
A-94 | 2-F,6-Cl | 2-Cl |
A-95 | 2-F,5-Cl | 2-Cl |
A-96 | 2-F,3-Cl | 2-Cl |
A-97 | 2-F,4-Cl | 2-Cl |
A-98 | 3-F,4-Cl | 2-Cl |
A-99 | 3-F,5-Cl | 2-Cl |
A-100 | 2-Cl,6-F | 2-Cl |
A-101 | 2-Cl,5-F | 2-Cl |
A-102 | 2-Cl,3-F | 2-Cl |
A-103 | 2-Cl,4-F | 2-Cl |
A-104 | 3-Cl,4-F | 2-Cl |
A-105 | 3-OCH<sub>3</sub>,5-Cl | 2-Cl |
A-106 | 3-OCH<sub>3</sub>,4-Cl | 2-Cl |
A-107 | 3-OCH<sub>3</sub>,2-Cl | 2-Cl |
A-108 | 4-OCH<sub>3</sub>,3-Cl | 2-Cl |
A-109 | 4-OCH<sub>3</sub>,2-Cl | 2-Cl |
A-110 | 2-OCH<sub>3</sub>,3-Cl | 2-Cl |
A-111 | 2-OCH<sub>3</sub>,4-Cl | 2-Cl |
A-112 | 2-OCH<sub>3</sub>,5-Cl | 2-Cl |
A-113 | 2-OCH<sub>3</sub>,6-Cl | 2-Cl |
A-114 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-Cl |
A-115 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-Cl |
A-116 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 2-Cl |
A-117 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 2-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-118 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-Cl |
A-119 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-Cl |
A-120 | - | 2-F |
A-121 | 2-Cl | 2-F |
A-122 | 2-F | 2-F |
A-123 | 2-Br | 2-F |
A-124 | 2-OCH<sub>3</sub> | 2-F |
A-125 | 2-CF<sub>3</sub> | 2-F |
A-126 | 2-C<sub>6</sub>H<sub>5</sub> | 2-F |
A-127 | 2-CH<sub>3</sub> | 2-F |
A-128 | 3-Cl | 2-F |
A-129 | 3-F | 2-F |
A-130 | 3-Br | 2-F |
A-131 | 3-OCH<sub>3</sub> | 2-F |
A-132 | 3-CF<sub>3</sub> | 2-F |
A-133 | 3-C<sub>6</sub>H<sub>5</sub> | 2-F |
A-134 | 3-CH<sub>3</sub> | 2-F |
A-135 | 4-Cl | 2-F |
A-136 | 4-F | 2-F |
A-137 | 4-Br | 2-F |
A-138 | 4-OCH<sub>3</sub> | 2-F |
A-139 | 4-CF<sub>3</sub> | 2-F |
A-140 | 4-C<sub>6</sub>H<sub>5</sub> | 2-F |
A-141 | 4-CH<sub>3</sub> | 2-F |
A-142 | 2-Cl,6-Cl | 2-F |
A-143 | 2-Cl,5-Cl | 2-F |
A-144 | 2-Cl,3-Cl | 2-F |
A-145 | 2-Cl,4-Cl | 2-F |
A-146 | 3-Cl,4-Cl | 2-F |
A-147 | 3-Cl,5-Cl | 2-F |
A-148 | 2-F,6-F | 2-F |
A-149 | 2-F,5-F | 2-F |
A-150 | 2-F,3-F | 2-F |
A-151 | 2-F,4-F | 2-F |
A-152 | 3-F,4-F | 2-F |
A-153 | 3-F,5-F | 2-F |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-154 | 2-F,6-Cl | 2-F |
A-155 | 2-F,5-Cl | 2-F |
A-156 | 2-F,3-Cl | 2-F |
A-157 | 2-F,4-Cl | 2-F |
A-158 | 3-F,4-Cl | 2-F |
A-159 | 3-F,5-Cl | 2-F |
A-160 | 2-Cl,6-F | 2-F |
A-161 | 2-Cl,5-F | 2-F |
A-162 | 2-Cl,3-F | 2-F |
A-163 | 2-Cl,4-F | 2-F |
A-164 | 3-Cl,4-F | 2-F |
A-165 | 3-OCH<sub>3</sub>,4-Cl | 2-F |
A-166 | 3-OCH<sub>3</sub>,2-Cl | 2-F |
A-167 | 4-OCH<sub>3</sub>,3-Cl | 2-F |
A-168 | 4-OCH<sub>3</sub>,2-Cl | 2-F |
A-169 | 2-OCH<sub>3</sub>,3-Cl | 2-F |
A-170 | 2-OCH<sub>3</sub>,4-Cl | 2-F |
A-171 | 2-OCH<sub>3</sub>,5-Cl | 2-F |
A-172 | 2-OCH<sub>3</sub>,6-Cl | 2-F |
A-173 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-F |
A-174 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-F |
A-175 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 2-F |
A-176 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 2-F |
A-177 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-F |
A-178 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-F |
A-179 | - | 2-Br |
A-180 | 2-Cl | 2-Br |
A-181 | 2-F | 2-Br |
A-182 | 2-Br | 2-Br |
A-183 | 2-OCH<sub>3</sub> | 2-Br |
A-184 | 2-CF<sub>3</sub> | 2-Br |
A-185 | 2-C<sub>6</sub>H<sub>5</sub> | 2-Br |
A-186 | 2-CH<sub>3</sub> | 2-Br |
A-187 | 3-Cl | 2-Br |
A-188 | 3-F | 2-Br |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-189 | 3-Br | 2-Br |
A-190 | 3-OCH<sub>3</sub> | 2-Br |
A-191 | 3-CF<sub>3</sub> | 2-Br |
A-192 | 3-C<sub>6</sub>H<sub>5</sub> | 2-Br |
A-193 | 3-CH<sub>3</sub> | 2-Br |
A-194 | 4-Cl | 2-Br |
A-195 | 4-F | 2-Br |
A-196 | 4-Br | 2-Br |
A-197 | 4-OCH<sub>3</sub> | 2-Br |
A-198 | 4-CF<sub>3</sub> | 2-Br |
A-199 | 4-C<sub>6</sub>H<sub>5</sub> | 2-Br |
A-200 | 4-CH<sub>3</sub> | 2-Br |
A-201 | 2-Cl,6-Cl | 2-Br |
A-202 | 2-Cl,5-Cl | 2-Br |
A-203 | 2-Cl,3-Cl | 2-Br |
A-204 | 2-Cl,4-Cl | 2-Br |
A-205 | 3-Cl,4-Cl | 2-Br |
A-206 | 3-Cl,5-Cl | 2-Br |
A-207 | 2-F,6-F | 2-Br |
A-208 | 2-F,5-F | 2-Br |
A-209 | 2-F,3-F | 2-Br |
A-210 | 2-F,4-F | 2-Br |
A-211 | 3-F,4-F | 2-Br |
A-212 | 3-F,5-F | 2-Br |
A-213 | 2-F,6-Cl | 2-Br |
A-214 | 2-F,5-Cl | 2-Br |
A-215 | 2-F,3-Cl | 2-Br |
A-216 | 2-F,4-Cl | 2-Br |
A-217 | 3-F,4-Cl | 2-Br |
A-218 | 3-F,5-Cl | 2-Br |
A-219 | 2-Cl,6-F | 2-Br |
A-220 | 2-Cl,5-F | 2-Br |
A-221 | 2-Cl,3-F | 2-Br |
A-222 | 2-Cl,4-F | 2-Br |
A-223 | 3-Cl,4-F | 2-Br |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-224 | 3-OCH<sub>3</sub>,4-Cl | 2-Br |
A-225 | 3-OCH<sub>3</sub>,2-Cl | 2-Br |
A-226 | 4-OCH<sub>3</sub>,3-Cl | 2-Br |
A-227 | 4-OCH<sub>3</sub>,2-Cl | 2-Br |
A-228 | 2-OCH<sub>3</sub>,3-Cl | 2-Br |
A-229 | 2-OCH<sub>3</sub>,4-Cl | 2-Br |
A-230 | 2-OCH<sub>3</sub>,5-Cl | 2-Br |
A-231 | 2-OCH<sub>3</sub>,6-Cl | 2-Br |
A-232 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-Br |
A-233 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-Br |
A-234 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 2-Br |
A-235 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 2-Br |
A-236 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-Br |
A-237 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-Br |
A-238 | - | 2-CH<sub>3</sub> |
A-239 | 2-Cl | 2-CH<sub>3</sub> |
A-240 | 2-F | 2-CH<sub>3</sub> |
A-241 | 2-Br | 2-CH<sub>3</sub> |
A-242 | 2-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-243 | 2-CF<sub>3</sub> | 2-CH<sub>3</sub> |
A-244 | 2-C<sub>6</sub>H<sub>5</sub> | 2-CH<sub>3</sub> |
A-245 | 2-CH<sub>3</sub> | 2-CH<sub>3</sub> |
A-246 | 3-Cl | 2-CH<sub>3</sub> |
A-247 | 3-F | 2-CH<sub>3</sub> |
A-248 | 3-Br | 2-CH<sub>3</sub> |
A-249 | 3-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-250 | 3-CF<sub>3</sub> | 2-CH<sub>3</sub> |
A-251 | 3-C<sub>6</sub>H<sub>5</sub> | 2-CH<sub>3</sub> |
A-252 | 3-CH<sub>3</sub> | 2-CH<sub>3</sub> |
A-253 | 4-Cl | 2-CH<sub>3</sub> |
A-254 | 4-F | 2-CH<sub>3</sub> |
A-255 | 4-Br | 2-CH<sub>3</sub> |
A-256 | 4-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-257 | 4-CF<sub>3</sub> | 2-CH<sub>3</sub> |
A-258 | 4-C<sub>6</sub>H<sub>5</sub> | 2-CH<sub>3</sub> |
A-259 | 4-CH<sub>3</sub> | 2-CH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-260 | 2-Cl,6-Cl | 2-CH<sub>3</sub> |
A-261 | 2-Cl,5-Cl | 2-CH<sub>3</sub> |
A-262 | 2-Cl,3-Cl | 2-CH<sub>3</sub> |
A-263 | 2-Cl,4-Cl | 2-CH<sub>3</sub> |
A-264 | 3-Cl,4-Cl | 2-CH<sub>3</sub> |
A-265 | 3-Cl,5-Cl | 2-CH<sub>3</sub> |
A-266 | 2-F,6-F | 2-CH<sub>3</sub> |
A-267 | 2-F,5-F | 2-CH<sub>3</sub> |
A-268 | 2-F,3-F | 2-CH<sub>3</sub> |
A-269 | 2-F,4-F | 2-CH<sub>3</sub> |
A-270 | 3-F,4-F | 2-CH<sub>3</sub> |
A-271 | 3-F,5-F | 2-CH<sub>3</sub> |
A-272 | 2-F,6-Cl | 2-CH<sub>3</sub> |
A-273 | 2-F,5-Cl | 2-CH<sub>3</sub> |
A-274 | 2-F,3-Cl | 2-CH<sub>3</sub> |
A-275 | 2-F,4-Cl | 2-CH<sub>3</sub> |
A-276 | 3-F,4-Cl | 2-CH<sub>3</sub> |
A-277 | 3-F,5-Cl | 2-CH<sub>3</sub> |
A-278 | 2-Cl,6-F | 2-CH<sub>3</sub> |
A-279 | 2-Cl,5-F | 2-CH<sub>3</sub> |
A-280 | 2-Cl,3-F | 2-CH<sub>3</sub> |
A-281 | 2-Cl,4-F | 2-CH<sub>3</sub> |
A-282 | 3-Cl,4-F | 2-CH<sub>3</sub> |
A-283 | 3-OCH<sub>3</sub>,4-Cl | 2-CH<sub>3</sub> |
A-284 | 3-OCH<sub>3</sub>,2-Cl | 2-CH<sub>3</sub> |
A-285 | 4-OCH<sub>3</sub>,3-Cl | 2-CH<sub>3</sub> |
A-286 | 4-OCH<sub>3</sub>,2-Cl | 2-CH<sub>3</sub> |
A-287 | 2-OCH<sub>3</sub>,3-Cl | 2-CH<sub>3</sub> |
A-288 | 2-OCH<sub>3</sub>,4-Cl | 2-CH<sub>3</sub> |
A-289 | 2-OCH<sub>3</sub>,5-Cl | 2-CH<sub>3</sub> |
A-290 | 2-OCH<sub>3</sub>,6-Cl | 2-CH<sub>3</sub> |
A-291 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-292 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-293 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-294 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-295 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-296 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-CH<sub>3</sub> |
A-297 | - | 2-CF<sub>3</sub> |
A-298 | 2-Cl | 2-CF<sub>3</sub> |
A-299 | 2-F | 2-CF<sub>3</sub> |
A-300 | 2-Br | 2-CF<sub>3</sub> |
A-301 | 2-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-302 | 2-CF<sub>3</sub> | 2-CF<sub>3</sub> |
A-303 | 2-C<sub>6</sub>H<sub>5</sub> | 2-CF<sub>3</sub> |
A-304 | 2-CH<sub>3</sub> | 2-CF<sub>3</sub> |
A-305 | 3-Cl | 2-CF<sub>3</sub> |
A-306 | 3-F | 2-CF<sub>3</sub> |
A-307 | 3-Br | 2-CF<sub>3</sub> |
A-308 | 3-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-309 | 3-CF<sub>3</sub> | 2-CF<sub>3</sub> |
A-310 | 3-C<sub>6</sub>H<sub>5</sub> | 2-CF<sub>3</sub> |
A-311 | 3-CH<sub>3</sub> | 2-CF<sub>3</sub> |
A-312 | 4-Cl | 2-CF<sub>3</sub> |
A-313 | 4-F | 2-CF<sub>3</sub> |
A-314 | 4-Br | 2-CF<sub>3</sub> |
A-315 | 4-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-316 | 4-CF<sub>3</sub> | 2-CF<sub>3</sub> |
A-317 | 4-C<sub>6</sub>H<sub>5</sub> | 2-CF<sub>3</sub> |
A-318 | 4-CH<sub>3</sub> | 2-CF<sub>3</sub> |
A-319 | 2-Cl,6-Cl | 2-CF<sub>3</sub> |
A-320 | 2-Cl,5-Cl | 2-CF<sub>3</sub> |
A-321 | 2-Cl,3-Cl | 2-CF<sub>3</sub> |
A-322 | 2-Cl,4-Cl | 2-CF<sub>3</sub> |
A-323 | 3-Cl,4-Cl | 2-CF<sub>3</sub> |
A-324 | 3-Cl,5-Cl | 2-CF<sub>3</sub> |
A-325 | 2-F,6-F | 2-CF<sub>3</sub> |
A-326 | 2-F,5-F | 2-CF<sub>3</sub> |
A-327 | 2-F,3-F | 2-CF<sub>3</sub> |
A-328 | 2-F,4-F | 2-CF<sub>3</sub> |
A-329 | 3-F,4-F | 2-CF<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-330 | 3-F,5-F | 2-CF<sub>3</sub> |
A-331 | 2-F,6-Cl | 2-CF<sub>3</sub> |
A-332 | 2-F,5-Cl | 2-CF<sub>3</sub> |
A-333 | 2-F,3-Cl | 2-CF<sub>3</sub> |
A-334 | 2-F,4-Cl | 2-CF<sub>3</sub> |
A-335 | 3-F,4-Cl | 2-CF<sub>3</sub> |
A-336 | 3-F,5-Cl | 2-CF<sub>3</sub> |
A-337 | 2-Cl,6-F | 2-CF<sub>3</sub> |
A-338 | 2-Cl,5-F | 2-CF<sub>3</sub> |
A-339 | 2-Cl,3-F | 2-CF<sub>3</sub> |
A-340 | 2-Cl,4-F | 2-CF<sub>3</sub> |
A-341 | 3-Cl,4-F | 2-CF<sub>3</sub> |
A-342 | 3-OCH<sub>3</sub>,4-Cl | 2-CF<sub>3</sub> |
A-343 | 3-OCH<sub>3</sub>,2-Cl | 2-CF<sub>3</sub> |
A-344 | 4-OCH<sub>3</sub>,3-Cl | 2-CF<sub>3</sub> |
A-345 | 4-OCH<sub>3</sub>,2-Cl | 2-CF<sub>3</sub> |
A-346 | 2-OCH<sub>3</sub>,3-Cl | 2-CF<sub>3</sub> |
A-347 | 2-OCH<sub>3</sub>,4-Cl | 2-CF<sub>3</sub> |
A-348 | 2-OCH<sub>3</sub>,5-Cl | 2-CF<sub>3</sub> |
A-349 | 2-OCH<sub>3</sub>,6-Cl | 2-CF<sub>3</sub> |
A-350 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-351 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-352 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-353 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-354 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-355 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-CF<sub>3</sub> |
A-356 | - | 2-OCH<sub>3</sub> |
A-357 | 2-Cl | 2-OCH<sub>3</sub> |
A-358 | 2-F | 2-OCH<sub>3</sub> |
A-359 | 2-Br | 2-OCH<sub>3</sub> |
A-360 | 2-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-361 | 2-CF<sub>3</sub> | 2-OCH<sub>3</sub> |
A-362 | 2-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub> |
A-363 | 2-CH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-364 | 3-Cl | 2-OCH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-365 | 3-F | 2-OCH<sub>3</sub> |
A-366 | 3-Br | 2-OCH<sub>3</sub> |
A-367 | 3-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-368 | 3-CF<sub>3</sub> | 2-OCH<sub>3</sub> |
A-369 | 3-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub> |
A-370 | 3-CH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-371 | 4-Cl | 2-OCH<sub>3</sub> |
A-372 | 4-F | 2-OCH<sub>3</sub> |
A-373 | 4-Br | 2-OCH<sub>3</sub> |
A-374 | 4-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-375 | 4-CF<sub>3</sub> | 2-OCH<sub>3</sub> |
A-376 | 4-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub> |
A-377 | 4-CH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-378 | 2-Cl,6-Cl | 2-OCH<sub>3</sub> |
A-379 | 2-Cl,5-Cl | 2-OCH<sub>3</sub> |
A-380 | 2-Cl,3-Cl | 2-OCH<sub>3</sub> |
A-381 | 2-Cl,4-Cl | 2-OCH<sub>3</sub> |
A-382 | 3-Cl,4-Cl | 2-OCH<sub>3</sub> |
A-383 | 3-Cl,5-Cl | 2-OCH<sub>3</sub> |
A-384 | 2-F,6-F | 2-OCH<sub>3</sub> |
A-385 | 2-F,5-F | 2-OCH<sub>3</sub> |
A-386 | 2-F,3-F | 2-OCH<sub>3</sub> |
A-387 | 2-F,4-F | 2-OCH<sub>3</sub> |
A-388 | 3-F,4-F | 2-OCH<sub>3</sub> |
A-389 | 3-F,5-F | 2-OCH<sub>3</sub> |
A-390 | 2-F,6-Cl | 2-OCH<sub>3</sub> |
A-391 | 2-F,5-Cl | 2-OCH<sub>3</sub> |
A-392 | 2-F,3-Cl | 2-OCH<sub>3</sub> |
A-393 | 2-F,4-Cl | 2-OCH<sub>3</sub> |
A-394 | 3-F,4-Cl | 2-OCH<sub>3</sub> |
A-395 | 3-F,5-Cl | 2-OCH<sub>3</sub> |
A-396 | 2-Cl,6-F | 2-OCH<sub>3</sub> |
A-397 | 2-Cl,5-F | 2-OCH<sub>3</sub> |
A-398 | 2-Cl,3-F | 2-OCH<sub>3</sub> |
A-399 | 2-Cl,4-F | 2-OCH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-400 | 3-Cl,4-F | 2-OCH<sub>3</sub> |
A-401 | 3-OCH<sub>3</sub>,4-Cl | 2-OCH<sub>3</sub> |
A-402 | 3-OCH<sub>3</sub>,2-Cl | 2-OCH<sub>3</sub> |
A-403 | 4-OCH<sub>3</sub>,3-Cl | 2-OCH<sub>3</sub> |
A-404 | 4-OCH<sub>3</sub>,2-Cl | 2-OCH<sub>3</sub> |
A-405 | 2-OCH<sub>3</sub>,3-Cl | 2-OCH<sub>3</sub> |
A-406 | 2-OCH<sub>3</sub>,4-Cl | 2-OCH<sub>3</sub> |
A-407 | 2-OCH<sub>3</sub>,5-Cl | 2-OCH<sub>3</sub> |
A-408 | 2-OCH<sub>3</sub>,6-Cl | 2-OCH<sub>3</sub> |
A-409 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-410 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-411 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-412 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-413 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-414 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 2-OCH<sub>3</sub> |
A-415 | - | 3-Cl |
A-416 | 2-Cl | 3-Cl |
A-417 | 2-F | 3-Cl |
A-418 | 2-Br | 3-Cl |
A-419 | 2-OCH<sub>3</sub> | 3-Cl |
A-420 | 2-CF<sub>3</sub> | 3-Cl |
A-421 | 2-C<sub>6</sub>H<sub>5</sub> | 3-Cl |
A-422 | 2-CH<sub>3</sub> | 3-Cl |
A-423 | 3-Cl | 3-Cl |
A-424 | 3-F | 3-Cl |
A-425 | 3-Br | 3-Cl |
A-426 | 3-OCH<sub>3</sub> | 3-Cl |
A-427 | 3-CF<sub>3</sub> | 3-Cl |
A-428 | 3-C<sub>6</sub>H<sub>5</sub> | 3-Cl |
A-429 | 3-CH<sub>3</sub> | 3-Cl |
A-430 | 4-Cl | 3-Cl |
A-431 | 4-F | 3-Cl |
A-432 | 4-Br | 3-Cl |
A-433 | 4-OCH<sub>3</sub> | 3-Cl |
A-434 | 4-CF<sub>3</sub> | 3-Cl |
A-435 | 4-C<sub>6</sub>H<sub>5</sub> | 3-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-436 | 4-CH<sub>3</sub> | 3-Cl |
A-437 | 2-Cl,6-Cl | 3-Cl |
A-438 | 2-Cl,5-Cl | 3-Cl |
A-439 | 2-Cl,3-Cl | 3-Cl |
A-440 | 2-Cl,4-Cl | 3-Cl |
A-441 | 3-Cl,4-Cl | 3-Cl |
A-442 | 3-Cl,5-Cl | 3-Cl |
A-443 | 2-F,6-F | 3-Cl |
A-444 | 2-F,5-F | 3-Cl |
A-445 | 2-F,3-F | 3-Cl |
A-446 | 2-F,4-F | 3-Cl |
A-447 | 3-F,4-F | 3-Cl |
A-448 | 3-F,5-F | 3-Cl |
A-449 | 2-F,6-Cl | 3-Cl |
A-450 | 2-F,5-Cl | 3-Cl |
A-451 | 2-F,3-Cl | 3-Cl |
A-452 | 2-F,4-Cl | 3-Cl |
A-453 | 3-F,4-Cl | 3-Cl |
A-454 | 3-F,5-Cl | 3-Cl |
A-455 | 2-Cl,6-F | 3-Cl |
A-456 | 2-Cl,5-F | 3-Cl |
A-457 | 2-Cl,3-F | 3-Cl |
A-458 | 2-Cl,4-F | 3-Cl |
A-459 | 3-Cl,4-F | 3-Cl |
A-460 | 3-OCH<sub>3</sub>,4-Cl | 3-Cl |
A-461 | 3-OCH<sub>3</sub>,2-Cl | 3-Cl |
A-462 | 4-OCH<sub>3</sub>,3-Cl | 3-Cl |
A-463 | 4-OCH<sub>3</sub>,2-Cl | 3-Cl |
A-464 | 2-OCH<sub>3</sub>,3-Cl | 3-Cl |
A-465 | 2-OCH<sub>3</sub>,4-Cl | 3-Cl |
A-466 | 2-OCH<sub>3</sub>,5-Cl | 3-Cl |
A-467 | 2-OCH<sub>3</sub>,6-Cl | 3-Cl |
A-468 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-Cl |
A-469 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-470 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 3-Cl |
A-471 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 3-Cl |
A-472 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-Cl |
A-473 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-Cl |
A-474 | - | 3-Br |
A-475 | 2-Cl | 3-Br |
A-476 | 2-F | 3-Br |
A-477 | 2-Br | 3-Br |
A-478 | 2-OCH<sub>3</sub> | 3-Br |
A-479 | 2-CF<sub>3</sub> | 3-Br |
A-480 | 2-C<sub>6</sub>H<sub>5</sub> | 3-Br |
A-481 | 2-CH<sub>3</sub> | 3-Br |
A-482 | 3-Cl | 3-Br |
A-483 | 3-F | 3-Br |
A-484 | 3-Br | 3-Br |
A-485 | 3-OCH<sub>3</sub> | 3-Br |
A-486 | 3-CF<sub>3</sub> | 3-Br |
A-487 | 3-C<sub>6</sub>H<sub>5</sub> | 3-Br |
A-488 | 3-CH<sub>3</sub> | 3-Br |
A-489 | 4-Cl | 3-Br |
A-490 | 4-F | 3-Br |
A-491 | 4-Br | 3-Br |
A-492 | 4-OCH<sub>3</sub> | 3-Br |
A-493 | 4-CF<sub>3</sub> | 3-Br |
A-494 | 4-C<sub>6</sub>H<sub>5</sub> | 3-Br |
A-495 | 4-CH<sub>3</sub> | 3-Br |
A-496 | 2-Cl,6-Cl | 3-Br |
A-497 | 2-Cl,5-Cl | 3-Br |
A-498 | 2-Cl,3-Cl | 3-Br |
A-499 | 2-Cl,4-Cl | 3-Br |
A-500 | 3-Cl,4-Cl | 3-Br |
A-501 | 3-Cl,5-Cl | 3-Br |
A-502 | 2-F,6-F | 3-Br |
A-503 | 2-F,5-F | 3-Br |
A-504 | 2-F,3-F | 3-Br |
A-505 | 2-F,4-F | 3-Br |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-506 | 3-F,4-F | 3-Br |
A-507 | 3-F,5-F | 3-Br |
A-508 | 2-F,6-Cl | 3-Br |
A-509 | 2-F,5-Cl | 3-Br |
A-510 | 2-F,3-Cl | 3-Br |
A-511 | 2-F,4-Cl | 3-Br |
A-512 | 3-F,4-Cl | 3-Br |
A-513 | 3-F,5-Cl | 3-Br |
A-514 | 2-Cl,6-F | 3-Br |
A-515 | 2-Cl,5-F | 3-Br |
A-516 | 2-Cl,3-F | 3-Br |
A-517 | 2-Cl,4-F | 3-Br |
A-518 | 3-Cl,4-F | 3-Br |
A-519 | 3-OCH<sub>3</sub>,4-Cl | 3-Br |
A-520 | 3-OCH<sub>3</sub>,2-Cl | 3-Br |
A-521 | 4-OCH<sub>3</sub>,3-Cl | 3-Br |
A-522 | 4-OCH<sub>3</sub>,2-Cl | 3-Br |
A-523 | 2-OCH<sub>3</sub>,3-Cl | 3-Br |
A-524 | 2-OCH<sub>3</sub>,4-Cl | 3-Br |
A-525 | 2-OCH<sub>3</sub>,5-Cl | 3-Br |
A-526 | 2-OCH<sub>3</sub>,6-Cl | 3-Br |
A-527 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-Br |
A-528 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-Br |
A-529 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 3-Br |
A-530 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 3-Br |
A-531 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-Br |
A-532 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-Br |
A-533 | - | 3-F |
A-534 | 2-Cl | 3-F |
A-535 | 2-F | 3-F |
A-536 | 2-Br | 3-F |
A-537 | 2-OCH<sub>3</sub> | 3-F |
A-538 | 2-CF<sub>3</sub> | 3-F |
A-539 | 2-C<sub>6</sub>H<sub>5</sub> | 3-F |
A-540 | 2-CH<sub>3</sub> | 3-F |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-541 | 3-Cl | 3-F |
A-542 | 3-F | 3-F |
A-543 | 3-Br | 3-F |
A-544 | 3-OCH<sub>3</sub> | 3-F |
A-545 | 3-CF<sub>3</sub> | 3-F |
A-546 | 3-C<sub>6</sub>H<sub>5</sub> | 3-F |
A-547 | 3-CH<sub>3</sub> | 3-F |
A-548 | 4-Cl | 3-F |
A-549 | 4-F | 3-F |
A-550 | 4-Br | 3-F |
A-551 | 4-OCH<sub>3</sub> | 3-F |
A-552 | 4-CF<sub>3</sub> | 3-F |
A-553 | 4-C<sub>6</sub>H<sub>5</sub> | 3-F |
A-554 | 4-CH<sub>3</sub> | 3-F |
A-555 | 2-Cl,6-Cl | 3-F |
A-556 | 2-Cl,5-Cl | 3-F |
A-557 | 2-Cl,3-Cl | 3-F |
A-558 | 2-Cl,4-Cl | 3-F |
A-559 | 3-Cl,4-Cl | 3-F |
A-560 | 3-Cl,5-Cl | 3-F |
A-561 | 2-F,6-F | 3-F |
A-562 | 2-F,5-F | 3-F |
A-563 | 2-F,3-F | 3-F |
A-564 | 2-F,4-F | 3-F |
A-565 | 3-F,4-F | 3-F |
A-566 | 3-F,5-F | 3-F |
A-567 | 2-F,6-Cl | 3-F |
A-568 | 2-F,5-Cl | 3-F |
A-569 | 2-F,3-Cl | 3-F |
A-570 | 2-F,4-Cl | 3-F |
A-571 | 3-F,4-Cl | 3-F |
A-572 | 3-F,5-Cl | 3-F |
A-573 | 2-Cl,6-F | 3-F |
A-574 | 2-Cl,5-F | 3-F |
A-575 | 2-Cl,3-F | 3-F |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-576 | 2-Cl,4-F | 3-F |
A-577 | 3-Cl,4-F | 3-F |
A-578 | 3-OCH<sub>3</sub>,4-Cl | 3-F |
A-579 | 3-OCH<sub>3</sub>,2-Cl | 3-F |
A-580 | 4-OCH<sub>3</sub>,3-Cl | 3-F |
A-581 | 4-OCH<sub>3</sub>,2-Cl | 3-F |
A-582 | 2-OCH<sub>3</sub>,3-Cl | 3-F |
A-583 | 2-OCH<sub>3</sub>,4-Cl | 3-F |
A-584 | 2-OCH<sub>3</sub>,5-Cl | 3-F |
A-585 | 2-OCH<sub>3</sub>,6-Cl | 3-F |
A-586 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-F |
A-587 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-F |
A-588 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 3-F |
A-589 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 3-F |
A-590 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-F |
A-591 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-F |
A-592 | - | 3-F |
A-593 | 2-Cl | 3-CH<sub>3</sub> |
A-594 | 2-F | 3-CH<sub>3</sub> |
A-595 | 2-Br | 3-CH<sub>3</sub> |
A-596 | 2-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-597 | 2-CF<sub>3</sub> | 3-CH<sub>3</sub> |
A-598 | 2-C<sub>6</sub>H<sub>5</sub> | 3-CH<sub>3</sub> |
A-599 | 2-CH<sub>3</sub> | 3-CH<sub>3</sub> |
A-600 | 3-Cl | 3-CH<sub>3</sub> |
A-601 | 3-F | 3-CH<sub>3</sub> |
A-602 | 3-Br | 3-CH<sub>3</sub> |
A-603 | 3-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-604 | 3-CF<sub>3</sub> | 3-CH<sub>3</sub> |
A-605 | 3-C<sub>6</sub>H<sub>5</sub> | 3-CH<sub>3</sub> |
A-606 | 3-CH<sub>3</sub> | 3-CH<sub>3</sub> |
A-607 | 4-Cl | 3-CH<sub>3</sub> |
A-608 | 4-F | 3-CH<sub>3</sub> |
A-609 | 4-Br | 3-CH<sub>3</sub> |
A-610 | 4-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-611 | 4-CF<sub>3</sub> | 3-CH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-612 | 4-C<sub>6</sub>H<sub>5</sub> | 3-CH<sub>3</sub> |
A-613 | 4-CH<sub>3</sub> | 3-CH<sub>3</sub> |
A-614 | 2-Cl,6-Cl | 3-CH<sub>3</sub> |
A-615 | 2-Cl,5-Cl | 3-CH<sub>3</sub> |
A-616 | 2-Cl,3-Cl | 3-CH<sub>3</sub> |
A-617 | 2-Cl,4-Cl | 3-CH<sub>3</sub> |
A-618 | 3-Cl,4-Cl | 3-CH<sub>3</sub> |
A-619 | 3-Cl,5-Cl | 3-CH<sub>3</sub> |
A-620 | 2-F,6-F | 3-CH<sub>3</sub> |
A-621 | 2-F,5-F | 3-CH<sub>3</sub> |
A-622 | 2-F,3-F | 3-CH<sub>3</sub> |
A-623 | 2-F,4-F | 3-CH<sub>3</sub> |
A-624 | 3-F,4-F | 3-CH<sub>3</sub> |
A-625 | 3-F,5-F | 3-CH<sub>3</sub> |
A-626 | 2-F,6-Cl | 3-CH<sub>3</sub> |
A-627 | 2-F,5-Cl | 3-CH<sub>3</sub> |
A-628 | 2-F,3-Cl | 3-CH<sub>3</sub> |
A-629 | 2-F,4-Cl | 3-CH<sub>3</sub> |
A-630 | 3-F,4-Cl | 3-CH<sub>3</sub> |
A-631 | 3-F,5-Cl | 3-CH<sub>3</sub> |
A-632 | 2-Cl,6-F | 3-CH<sub>3</sub> |
A-633 | 2-Cl,5-F | 3-CH<sub>3</sub> |
A-634 | 2-Cl,3-F | 3-CH<sub>3</sub> |
A-635 | 2-Cl,4-F | 3-CH<sub>3</sub> |
A-636 | 3-Cl,4-F | 3-CH<sub>3</sub> |
A-637 | 3-OCH<sub>3</sub>,4-Cl | 3-CH<sub>3</sub> |
A-638 | 3-OCH<sub>3</sub>,2-Cl | 3-CH<sub>3</sub> |
A-639 | 4-OCH<sub>3</sub>,3-Cl | 3-CH<sub>3</sub> |
A-640 | 4-OCH<sub>3</sub>,2-Cl | 3-CH<sub>3</sub> |
A-641 | 2-OCH<sub>3</sub>,3-Cl | 3-CH<sub>3</sub> |
A-642 | 2-OCH<sub>3</sub>,4-Cl | 3-CH<sub>3</sub> |
A-643 | 2-OCH<sub>3</sub>,5-Cl | 3-CH<sub>3</sub> |
A-644 | 2-OCH<sub>3</sub>,6-Cl | 3-CH<sub>3</sub> |
A-645 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-646 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-647 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-648 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-649 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-650 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-CH<sub>3</sub> |
A-651 | - | 3-CF<sub>3</sub> |
A-652 | 2-Cl | 3-CF<sub>3</sub> |
A-653 | 2-F | 3-CF<sub>3</sub> |
A-654 | 2-Br | 3-CF<sub>3</sub> |
A-655 | 2-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-656 | 2-CF<sub>3</sub> | 3-CF<sub>3</sub> |
A-657 | 2-C<sub>6</sub>H<sub>5</sub> | 3-CF<sub>3</sub> |
A-658 | 2-CH<sub>3</sub> | 3-CF<sub>3</sub> |
A-659 | 3-Cl | 3-CF<sub>3</sub> |
A-660 | 3-F | 3-CF<sub>3</sub> |
A-661 | 3-Br | 3-CF<sub>3</sub> |
A-662 | 3-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-663 | 3-CF<sub>3</sub> | 3-CF<sub>3</sub> |
A-664 | 3-C<sub>6</sub>H<sub>5</sub> | 3-CF<sub>3</sub> |
A-665 | 3-CH<sub>3</sub> | 3-CF<sub>3</sub> |
A-666 | 4-Cl | 3-CF<sub>3</sub> |
A-667 | 4-F | 3-CF<sub>3</sub> |
A-668 | 4-Br | 3-CF<sub>3</sub> |
A-669 | 4-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-670 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub> |
A-671 | 4-C<sub>6</sub>H<sub>5</sub> | 3-CF<sub>3</sub> |
A-672 | 4-CH<sub>3</sub> | 3-CF<sub>3</sub> |
A-673 | 2-Cl,6-Cl | 3-CF<sub>3</sub> |
A-674 | 2-Cl,5-Cl | 3-CF<sub>3</sub> |
A-675 | 2-Cl,3-Cl | 3-CF<sub>3</sub> |
A-676 | 2-Cl,4-Cl | 3-CF<sub>3</sub> |
A-677 | 3-Cl,4-Cl | 3-CF<sub>3</sub> |
A-678 | 3-Cl,5-Cl | 3-CF<sub>3</sub> |
A-679 | 2-F,6-F | 3-CF<sub>3</sub> |
A-680 | 2-F,5-F | 3-CF<sub>3</sub> |
A-681 | 2-F,3-F | 3-CF<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-682 | 2-F,4-F | 3-CF<sub>3</sub> |
A-683 | 3-F,4-F | 3-CF<sub>3</sub> |
A-684 | 3-F,5-F | 3-CF<sub>3</sub> |
A-685 | 2-F,6-Cl | 3-CF<sub>3</sub> |
A-686 | 2-F,5-Cl | 3-CF<sub>3</sub> |
A-687 | 2-F,3-Cl | 3-CF<sub>3</sub> |
A-688 | 2-F,4-Cl | 3-CF<sub>3</sub> |
A-689 | 3-F,4-Cl | 3-CF<sub>3</sub> |
A-690 | 3-F,5-Cl | 3-CF<sub>3</sub> |
A-691 | 2-Cl,6-F | 3-CF<sub>3</sub> |
A-692 | 2-Cl,5-F | 3-CF<sub>3</sub> |
A-693 | 2-Cl,3-F | 3-CF<sub>3</sub> |
A-694 | 2-Cl,4-F | 3-CF<sub>3</sub> |
A-695 | 3-Cl,4-F | 3-CF<sub>3</sub> |
A-696 | 3-OCH<sub>3</sub>,4-Cl | 3-CF<sub>3</sub> |
A-697 | 3-OCH<sub>3</sub>,2-Cl | 3-CF<sub>3</sub> |
A-698 | 4-OCH<sub>3</sub>,3-Cl | 3-CF<sub>3</sub> |
A-699 | 4-OCH<sub>3</sub>,2-Cl | 3-CF<sub>3</sub> |
A-700 | 2-OCH<sub>3</sub>,3-Cl | 3-CF<sub>3</sub> |
A-701 | 2-OCH<sub>3</sub>,4-Cl | 3-CF<sub>3</sub> |
A-702 | 2-OCH<sub>3</sub>,5-Cl | 3-CF<sub>3</sub> |
A-703 | 2-OCH<sub>3</sub>,6-Cl | 3-CF<sub>3</sub> |
A-704 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-705 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-706 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-707 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-708 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-709 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-CF<sub>3</sub> |
A-710 | - | 3-OCH<sub>3</sub> |
A-711 | 2-Cl | 3-OCH<sub>3</sub> |
A-712 | 2-F | 3-OCH<sub>3</sub> |
A-713 | 2-Br | 3-OCH<sub>3</sub> |
A-714 | 2-OCH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-715 | 2-CF<sub>3</sub> | 3-OCH<sub>3</sub> |
A-716 | 2-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-717 | 2-CH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-718 | 3-Cl | 3-OCH<sub>3</sub> |
A-719 | 3-F | 3-OCH<sub>3</sub> |
A-720 | 3-Br | 3-OCH<sub>3</sub> |
A-721 | 3-OCH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-722 | 3-CF<sub>3</sub> | 3-OCH<sub>3</sub> |
A-723 | 3-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub> |
A-724 | 3-CH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-725 | 4-Cl | 3-OCH<sub>3</sub> |
A-726 | 4-F | 3-OCH<sub>3</sub> |
A-727 | 4-Br | 3-OCH<sub>3</sub> |
A-728 | 4-OCH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-729 | 4-CF<sub>3</sub> | 3-OCH<sub>3</sub> |
A-730 | 4-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub> |
A-731 | 4-CH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-732 | 2-Cl,6-Cl | 3-OCH<sub>3</sub> |
A-733 | 2-Cl,5-Cl | 3-OCH<sub>3</sub> |
A-734 | 2-Cl,3-Cl | 3-OCH<sub>3</sub> |
A-735 | 2-Cl,4-Cl | 3-OCH<sub>3</sub> |
A-736 | 3-Cl,4-Cl | 3-OCH<sub>3</sub> |
A-737 | 3-Cl,5-Cl | 3-OCH<sub>3</sub> |
A-738 | 2-F,6-F | 3-OCH<sub>3</sub> |
A-739 | 2-F,5-F | 3-OCH<sub>3</sub> |
A-740 | 2-F,3-F | 3-OCH<sub>3</sub> |
A-741 | 2-F,4-F | 3-OCH<sub>3</sub> |
A-742 | 3-F,4-F | 3-OCH<sub>3</sub> |
A-743 | 3-F,5-F | 3-OCH<sub>3</sub> |
A-744 | 2-F,6-Cl | 3-OCH<sub>3</sub> |
A-745 | 2-F,5-Cl | 3-OCH<sub>3</sub> |
A-746 | 2-F,3-Cl | 3-OCH<sub>3</sub> |
A-747 | 2-F,4-Cl | 3-OCH<sub>3</sub> |
A-748 | 3-F,4-Cl | 3-OCH<sub>3</sub> |
A-749 | 3-F,5-Cl | 3-OCH<sub>3</sub> |
A-750 | 2-Cl,6-F | 3-OCH<sub>3</sub> |
A-751 | 2-Cl,5-F | 3-OCH<sub>3</sub> |
A-752 | 2-Cl,3-F | 3-OCH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-753 | 2-Cl,4-F | 3-OCH<sub>3</sub> |
A-754 | 3-Cl,4-F | 3-OCH<sub>3</sub> |
A-755 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-756 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 3-OCH<sub>3</sub> |
A-757 | - | 4-Cl |
A-758 | 2-Cl | 4-Cl |
A-759 | 2-F | 4-Cl |
A-760 | 2-Br | 4-Cl |
A-761 | 2-OCH<sub>3</sub> | 4-Cl |
A-762 | 2-CF<sub>3</sub> | 4-Cl |
A-763 | 2-C<sub>6</sub>H<sub>5</sub> | 4-Cl |
A-764 | 2-CH<sub>3</sub> | 4-Cl |
A-765 | 3-Cl | 4-Cl |
A-766 | 3-F | 4-Cl |
A-767 | 3-Br | 4-Cl |
A-768 | 3-OCH<sub>3</sub> | 4-Cl |
A-769 | 3-CF<sub>3</sub> | 4-Cl |
A-770 | 3-C<sub>6</sub>H<sub>5</sub> | 4-Cl |
A-771 | 3-CH<sub>3</sub> | 4-Cl |
A-772 | 4-Cl | 4-Cl |
A-773 | 4-F | 4-Cl |
A-774 | 4-Br | 4-Cl |
A-775 | 4-OCH<sub>3</sub> | 4-Cl |
A-776 | 4-CF<sub>3</sub> | 4-Cl |
A-777 | 4-C<sub>6</sub>H<sub>5</sub> | 4-Cl |
A-778 | 4-CH<sub>3</sub> | 4-Cl |
A-779 | 2-Cl,6-Cl | 4-Cl |
A-780 | 2-Cl,5-Cl | 4-Cl |
A-781 | 2-Cl,3-Cl | 4-Cl |
A-782 | 2-Cl,4-Cl | 4-Cl |
A-783 | 3-Cl,4-Cl | 4-Cl |
A-784 | 3-Cl,5-Cl | 4-Cl |
A-785 | 2-F,6-F | 4-Cl |
A-786 | 2-F,5-F | 4-Cl |
A-787 | 2-F,3-F | 4-Cl |
A-788 | 2-F,4-F | 4-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-789 | 3-F,4-F | 4-Cl |
A-790 | 3-F,5-F | 4-Cl |
A-791 | 2-F,6-Cl | 4-Cl |
A-792 | 2-F,5-Cl | 4-Cl |
A-793 | 2-F,3-Cl | 4-Cl |
A-794 | 2-F,4-Cl | 4-Cl |
A-795 | 3-F,4-Cl | 4-Cl |
A-796 | 3-F,5-Cl | 4-Cl |
A-797 | 2-Cl,6-F | 4-Cl |
A-798 | 2-Cl,5-F | 4-Cl |
A-799 | 2-Cl,3-F | 4-Cl |
A-800 | 2-Cl,4-F | 4-Cl |
A-801 | 3-Cl,4-F | 4-Cl |
A-802 | 3-OCH<sub>3</sub>,4-Cl | 4-Cl |
A-803 | 3-OCH<sub>3</sub>,2-Cl | 4-Cl |
A-804 | 4-OCH<sub>3</sub>,3-Cl | 4-Cl |
A-805 | 4-OCH<sub>3</sub>,2-Cl | 4-Cl |
A-806 | 2-OCH<sub>3</sub>,3-Cl | 4-Cl |
A-807 | 2-OCH<sub>3</sub>,4-Cl | 4-Cl |
A-808 | 2-OCH<sub>3</sub>,5-Cl | 4-Cl |
A-809 | 2-OCH<sub>3</sub>,6-Cl | 4-Cl |
A-810 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-Cl |
A-811 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-Cl |
A-812 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 4-Cl |
A-813 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 4-Cl |
A-814 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-Cl |
A-815 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-Cl |
A-816 | - | 4-F |
A-817 | 2-Cl | 4-F |
A-818 | 2-F | 4-F |
A-819 | 2-Br | 4-F |
A-820 | 2-OCH<sub>3</sub> | 4-F |
A-821 | 2-CF<sub>3</sub> | 4-F |
A-822 | 2-C<sub>6</sub>H<sub>5</sub> | 4-F |
A-823 | 2-CH<sub>3</sub> | 4-F |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-824 | 3-Cl | 4-F |
A-825 | 3-F | 4-F |
A-826 | 3-Br | 4-F |
A-827 | 3-OCH<sub>3</sub> | 4-F |
A-828 | 3-CF<sub>3</sub> | 4-F |
A-829 | 3-C<sub>6</sub>H<sub>5</sub> | 4-F |
A-830 | 3-CH<sub>3</sub> | 4-F |
A-831 | 4-Cl | 4-F |
A-832 | 4-F | 4-F |
A-833 | 4-Br | 4-F |
A-834 | 4-OCH<sub>3</sub> | 4-F |
A-835 | 4-CF<sub>3</sub> | 4-F |
A-836 | 4-C<sub>6</sub>H<sub>5</sub> | 4-F |
A-837 | 4-CH<sub>3</sub> | 4-F |
A-838 | 2-Cl,6-Cl | 4-F |
A-839 | 2-Cl,5-Cl | 4-F |
A-840 | 2-Cl,3-Cl | 4-F |
A-841 | 2-Cl,4-Cl | 4-F |
A-842 | 3-Cl,4-Cl | 4-F |
A-843 | 3-Cl,5-Cl | 4-F |
A-844 | 2-F,6-F | 4-F |
A-845 | 2-F,5-F | 4-F |
A-846 | 2-F,3-F | 4-F |
A-847 | 2-F,4-F | 4-F |
A-848 | 3-F,4-F | 4-F |
A-849 | 3-F,5-F | 4-F |
A-850 | 2-F,6-Cl | 4-F |
A-851 | 2-F,5-Cl | 4-F |
A-852 | 2-F,3-Cl | 4-F |
A-853 | 2-F,4-Cl | 4-F |
A-854 | 3-F,4-Cl | 4-F |
A-855 | 3-F,5-Cl | 4-F |
A-856 | 2-Cl,6-F | 4-F |
A-857 | 2-Cl,5-F | 4-F |
A-858 | 2-Cl,3-F | 4-F |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-859 | 2-Cl,4-F | 4-F |
A-860 | 3-Cl,4-F | 4-F |
A-861 | 3-OCH<sub>3</sub>,4-Cl | 4-F |
A-862 | 3-OCH<sub>3</sub>,2-Cl | 4-F |
A-863 | 4-OCH<sub>3</sub>,3-Cl | 4-F |
A-864 | 4-OCH<sub>3</sub>,2-Cl | 4-F |
A-865 | 2-OCH<sub>3</sub>,3-Cl | 4-F |
A-866 | 2-OCH<sub>3</sub>,4-Cl | 4-F |
A-867 | 2-OCH<sub>3</sub>,5-Cl | 4-F |
A-868 | 2-OCH<sub>3</sub>,6-Cl | 4-F |
A-869 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-F |
A-870 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-F |
A-871 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 4-F |
A-872 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 4-F |
A-873 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-F |
A-874 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-F |
A-875 | - | 4-OCH<sub>3</sub> |
A-876 | 2-Cl | 4-OCH<sub>3</sub> |
A-877 | 2-F | 4-OCH<sub>3</sub> |
A-878 | 2-Br | 4-OCH<sub>3</sub> |
A-879 | 2-OCH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-880 | 2-CF<sub>3</sub> | 4-OCH<sub>3</sub> |
A-881 | 2-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub> |
A-882 | 2-CH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-883 | 3-Cl | 4-OCH<sub>3</sub> |
A-884 | 3-F | 4-OCH<sub>3</sub> |
A-885 | 3-Br | 4-OCH<sub>3</sub> |
A-886 | 3-OCH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-887 | 3-CF<sub>3</sub> | 4-OCH<sub>3</sub> |
A-888 | 3-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub> |
A-889 | 3-CH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-890 | 4-Cl | 4-OCH<sub>3</sub> |
A-891 | 4-F | 4-OCH<sub>3</sub> |
A-892 | 4-Br | 4-OCH<sub>3</sub> |
A-893 | 4-OCH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-894 | 4-CF<sub>3</sub> | 4-OCH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-895 | 4-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub> |
A-896 | 4-CH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-897 | 2-Cl,6-Cl | 4-OCH<sub>3</sub> |
A-898 | 2-Cl,5-Cl | 4-OCH<sub>3</sub> |
A-899 | 2-Cl,3-Cl | 4-OCH<sub>3</sub> |
A-900 | 2-Cl,4-Cl | 4-OCH<sub>3</sub> |
A-901 | 3-Cl,4-Cl | 4-OCH<sub>3</sub> |
A-902 | 3-Cl,5-Cl | 4-OCH<sub>3</sub> |
A-903 | 2-F,6-F | 4-OCH<sub>3</sub> |
A-904 | 2-F,5-F | 4-OCH<sub>3</sub> |
A-905 | 2-F,3-F | 4-OCH<sub>3</sub> |
A-906 | 2-F,4-F | 4-OCH<sub>3</sub> |
A-907 | 3-F,4-F | 4-OCH<sub>3</sub> |
A-908 | 3-F,5-F | 4-OCH<sub>3</sub> |
A-909 | 2-F,6-Cl | 4-OCH<sub>3</sub> |
A-910 | 2-F,5-Cl | 4-OCH<sub>3</sub> |
A-911 | 2-F,3-Cl | 4-OCH<sub>3</sub> |
A-912 | 2-F,4-Cl | 4-OCH<sub>3</sub> |
A-913 | 3-F,4-Cl | 4-OCH<sub>3</sub> |
A-914 | 3-F,5-Cl | 4-OCH<sub>3</sub> |
A-915 | 2-Cl,6-F | 4-OCH<sub>3</sub> |
A-916 | 2-Cl,5-F | 4-OCH<sub>3</sub> |
A-917 | 2-Cl,3-F | 4-OCH<sub>3</sub> |
A-918 | 2-Cl,4-F | 4-OCH<sub>3</sub> |
A-919 | 3-Cl,4-F | 4-OCH<sub>3</sub> |
A-920 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-921 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-OCH<sub>3</sub> |
A-922 | - | 4-CH<sub>3</sub> |
A-923 | 2-Cl | 4-CH<sub>3</sub> |
A-924 | 2-F | 4-CH<sub>3</sub> |
A-925 | 2-Br | 4-CH<sub>3</sub> |
A-926 | 2-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-927 | 2-CF<sub>3</sub> | 4-CH<sub>3</sub> |
A-928 | 2-C<sub>6</sub>H<sub>5</sub> | 4-CH<sub>3</sub> |
A-929 | 2-CH<sub>3</sub> | 4-CH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-930 | 3-Cl | 4-CH<sub>3</sub> |
A-931 | 3-F | 4-CH<sub>3</sub> |
A-932 | 3-Br | 4-CH<sub>3</sub> |
A-933 | 3-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-934 | 3-CF<sub>3</sub> | 4-CH<sub>3</sub> |
A-935 | 3-C<sub>6</sub>H<sub>5</sub> | 4-CH<sub>3</sub> |
A-936 | 3-CH<sub>3</sub> | 4-CH<sub>3</sub> |
A-937 | 4-Cl | 4-CH<sub>3</sub> |
A-938 | 4-F | 4-CH<sub>3</sub> |
A-939 | 4-Br | 4-CH<sub>3</sub> |
A-940 | 4-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-941 | 4-CF<sub>3</sub> | 4-CH<sub>3</sub> |
A-942 | 4-C<sub>6</sub>H<sub>5</sub> | 4-CH<sub>3</sub> |
A-943 | 4-CH<sub>3</sub> | 4-CH<sub>3</sub> |
A-944 | 2-Cl,6-Cl | 4-CH<sub>3</sub> |
A-945 | 2-Cl,5-Cl | 4-CH<sub>3</sub> |
A-946 | 2-Cl,3-Cl | 4-CH<sub>3</sub> |
A-947 | 2-Cl,4-Cl | 4-CH<sub>3</sub> |
A-948 | 3-Cl,4-Cl | 4-CH<sub>3</sub> |
A-949 | 3-Cl,5-Cl | 4-CH<sub>3</sub> |
A-950 | 2-F,6-F | 4-CH<sub>3</sub> |
A-951 | 2-F,5-F | 4-CH<sub>3</sub> |
A-952 | 2-F,3-F | 4-CH<sub>3</sub> |
A-953 | 2-F,4-F | 4-CH<sub>3</sub> |
A-954 | 3-F,4-F | 4-CH<sub>3</sub> |
A-955 | 3-F,5-F | 4-CH<sub>3</sub> |
A-956 | 2-F,6-Cl | 4-CH<sub>3</sub> |
A-957 | 2-F,5-Cl | 4-CH<sub>3</sub> |
A-958 | 2-F,3-Cl | 4-CH<sub>3</sub> |
A-959 | 2-F,4-Cl | 4-CH<sub>3</sub> |
A-960 | 3-F,4-Cl | 4-CH<sub>3</sub> |
A-961 | 3-F,5-Cl | 4-CH<sub>3</sub> |
A-962 | 2-Cl,6-F | 4-CH<sub>3</sub> |
A-963 | 2-Cl,5-F | 4-CH<sub>3</sub> |
A-964 | 2-Cl,3-F | 4-CH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-965 | 2-Cl,4-F | 4-CH<sub>3</sub> |
A-966 | 3-Cl,4-F | 4-CH<sub>3</sub> |
A-967 | 3-OCH<sub>3</sub>,4-Cl | 4-CH<sub>3</sub> |
A-968 | 3-OCH<sub>3</sub>,2-Cl | 4-CH<sub>3</sub> |
A-969 | 4-OCH<sub>3</sub>,3-Cl | 4-CH<sub>3</sub> |
A-970 | 4-OCH<sub>3</sub>,2-Cl | 4-CH<sub>3</sub> |
A-971 | 2-OCH<sub>3</sub>,3-Cl | 4-CH<sub>3</sub> |
A-972 | 2-OCH<sub>3</sub>,4-Cl | 4-CH<sub>3</sub> |
A-973 | 2-OCH<sub>3</sub>,5-Cl | 4-CH<sub>3</sub> |
A-974 | 2-OCH<sub>3</sub>,6-Cl | 4-CH<sub>3</sub> |
A-975 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-976 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-977 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-978 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-979 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-980 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-CH<sub>3</sub> |
A-981 | - | 4-CF<sub>3</sub> |
A-982 | 2-Cl | 4-CF<sub>3</sub> |
A-983 | 2-F | 4-CF<sub>3</sub> |
A-984 | 2-Br | 4-CF<sub>3</sub> |
A-985 | 2-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-986 | 2-CF<sub>3</sub> | 4-CF<sub>3</sub> |
A-987 | 2-C<sub>6</sub>H<sub>5</sub> | 4-CF<sub>3</sub> |
A-988 | 2-CH<sub>3</sub> | 4-CF<sub>3</sub> |
A-989 | 3-Cl | 4-CF<sub>3</sub> |
A-990 | 3-F | 4-CF<sub>3</sub> |
A-991 | 3-Br | 4-CF<sub>3</sub> |
A-992 | 3-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-993 | 3-CF<sub>3</sub> | 4-CF<sub>3</sub> |
A-994 | 3-C<sub>6</sub>H<sub>5</sub> | 4-CF<sub>3</sub> |
A-995 | 3-CH<sub>3</sub> | 4-CF<sub>3</sub> |
A-996 | 4-Cl | 4-CF<sub>3</sub> |
A-997 | 4-F | 4-CF<sub>3</sub> |
A-998 | 4-Br | 4-CF<sub>3</sub> |
A-999 | 4-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-1000 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1001 | 4-C<sub>6</sub>H<sub>5</sub> | 4-CF<sub>3</sub> |
A-1002 | 4-CH<sub>3</sub> | 4-CF<sub>3</sub> |
A-1003 | 2-Cl,6-Cl | 4-CF<sub>3</sub> |
A-1004 | 2-Cl,5-Cl | 4-CF<sub>3</sub> |
A-1005 | 2-Cl,3-Cl | 4-CF<sub>3</sub> |
A-1006 | 2-Cl,4-Cl | 4-CF<sub>3</sub> |
A-1007 | 3-Cl,4-Cl | 4-CF<sub>3</sub> |
A-1008 | 3-Cl,5-Cl | 4-CF<sub>3</sub> |
A-1009 | 2-F,6-F | 4-CF<sub>3</sub> |
A-1010 | 2-F,5-F | 4-CF<sub>3</sub> |
A-1011 | 2-F,3-F | 4-CF<sub>3</sub> |
A-1012 | 2-F,4-F | 4-CF<sub>3</sub> |
A-1013 | 3-F,4-F | 4-CF<sub>3</sub> |
A-1014 | 3-F,5-F | 4-CF<sub>3</sub> |
A-1015 | 2-F,6-Cl | 4-CF<sub>3</sub> |
A-1016 | 2-F,5-Cl | 4-CF<sub>3</sub> |
A-1017 | 2-F,3-Cl | 4-CF<sub>3</sub> |
A-1018 | 2-F,4-Cl | 4-CF<sub>3</sub> |
A-1019 | 3-F,4-Cl | 4-CF<sub>3</sub> |
A-1020 | 3-F,5-Cl | 4-CF<sub>3</sub> |
A-1021 | 2-Cl,6-F | 4-CF<sub>3</sub> |
A-1022 | 2-Cl,5-F | 4-CF<sub>3</sub> |
A-1023 | 2-Cl,3-F | 4-CF<sub>3</sub> |
A-1024 | 2-Cl,4-F | 4-CF<sub>3</sub> |
A-1025 | 3-Cl,4-F | 4-CF<sub>3</sub> |
A-1026 | 3-OCH<sub>3</sub>,4-Cl | 4-CF<sub>3</sub> |
A-1027 | 3-OCH<sub>3</sub>,2-Cl | 4-CF<sub>3</sub> |
A-1028 | 4-OCH<sub>3</sub>,3-Cl | 4-CF<sub>3</sub> |
A-1029 | 4-OCH<sub>3</sub>,2-Cl | 4-CF<sub>3</sub> |
A-1030 | 2-OCH<sub>3</sub>,3-Cl | 4-CF<sub>3</sub> |
A-1031 | 2-OCH<sub>3</sub>,4-Cl | 4-CF<sub>3</sub> |
A-1032 | 2-OCH<sub>3</sub>,5-Cl | 4-CF<sub>3</sub> |
A-1033 | 2-OCH<sub>3</sub>,6-Cl | 4-CF<sub>3</sub> |
A-1034 | 2-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1035 | 2-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-1036 | 2-OCH<sub>3</sub>,3-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-1037 | 2-OCH<sub>3</sub>,6-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-1038 | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-1039 | 3-OCH<sub>3</sub>,4-OCH<sub>3</sub> | 4-CF<sub>3</sub> |
A-1040 | - | 3-Cl,4-Cl |
A-1041 | 2-Cl | 3-Cl,4-Cl |
A-1042 | 2-F | 3-Cl,4-Cl |
A-1043 | 2-Br | 3-Cl,4-Cl |
A-1044 | 2-OCH<sub>3</sub> | 3-Cl,4-Cl |
A-1045 | 2-CF<sub>3</sub> | 3-Cl,4-Cl |
A-1046 | 2-C<sub>6</sub>H<sub>5</sub> | 3-Cl,4-Cl |
A-1047 | 2-CH<sub>3</sub> | 3-Cl,4-Cl |
A-1048 | 3-Cl | 3-Cl,4-Cl |
A-1049 | 3-F | 3-Cl,4-Cl |
A-1050 | 3-Br | 3-Cl,4-Cl |
A-1051 | 3-OCH<sub>3</sub> | 3-Cl,4-Cl |
A-1052 | 3-CF<sub>3</sub> | 3-Cl,4-Cl |
A-1053 | 3-C<sub>6</sub>H<sub>5</sub> | 3-Cl,4-Cl |
A-1054 | 3-CH<sub>3</sub> | 3-Cl,4-Cl |
A-1055 | 4-Cl | 3-Cl,4-Cl |
A-1056 | 4-F | 3-Cl,4-Cl |
A-1057 | 4-Br | 3-Cl,4-Cl |
A-1058 | 4-OCH<sub>3</sub> | 3-Cl,4-Cl |
A-1059 | 4-CF<sub>3</sub> | 3-Cl,4-Cl |
A-1060 | 4-C<sub>6</sub>H<sub>5</sub> | 3-Cl,4-Cl |
A-1061 | 4-CH<sub>3</sub> | 3-Cl,4-Cl |
A-1062 | - | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1063 | 2-Cl | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1064 | 2-F | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1065 | 2-Br | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1066 | 2-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1067 | 2-CF<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1068 | 2-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1069 | 2-CH<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1070 | 3-Cl | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1071 | 3-F | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1072 | 3-Br | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1073 | 3-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1074 | 3-CF<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1075 | 3-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1076 | 3-CH<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1077 | 4-Cl | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1078 | 4-F | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1079 | 4-Br | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1080 | 4-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1081 | 4-CF<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1082 | 4-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1083 | 4-CH<sub>3</sub> | 3-OCH<sub>3</sub>,5-OCH<sub>3</sub> |
A-1084 | - | 3-OCH<sub>3</sub>,4-Cl |
A-1085 | 2-Cl | 3-OCH<sub>3</sub>,4-Cl |
A-1086 | 2-F | 3-OCH<sub>3</sub>,4-Cl |
A-1087 | 2-Br | 3-OCH<sub>3</sub>,4-Cl |
A-1088 | 2-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1089 | 2-CF<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1090 | 2-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1091 | 2-CH<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1092 | 3-Cl | 3-OCH<sub>3</sub>,4-Cl |
A-1093 | 3-F | 3-OCH<sub>3</sub>,4-Cl |
A-1094 | 3-Br | 3-OCH<sub>3</sub>,4-Cl |
A-1095 | 3-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1096 | 3-CF<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1097 | 3-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1098 | 3-CH<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1099 | 4-Cl | 3-OCH<sub>3</sub>,4-Cl |
A-1100 | 4-F | 3-OCH<sub>3</sub>,4-Cl |
A-1101 | 4-Br | 3-OCH<sub>3</sub>,4-Cl |
A-1102 | 4-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1103 | 4-CF<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1104 | 4-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1105 | 4-CH<sub>3</sub> | 3-OCH<sub>3</sub>,4-Cl |
A-1106 | - | 3-OCH<sub>3</sub>,2-Cl |
A-1107 | 2-Cl | 3-OCH<sub>3</sub>,2-Cl |
A-1108 | 2-F | 3-OCH<sub>3</sub>,2-Cl |
A-1109 | 2-Br | 3-OCH<sub>3</sub>,2-Cl |
A-1110 | 2-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1111 | 2-CF<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1112 | 2-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1113 | 2-CH<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1114 | 3-Cl | 3-OCH<sub>3</sub>,2-Cl |
A-1115 | 3-F | 3-OCH<sub>3</sub>,2-Cl |
A-1116 | 3-Br | 3-OCH<sub>3</sub>,2-Cl |
A-1117 | 3-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1118 | 3-CF<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1119 | 3-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1120 | 3-CH<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1121 | 4-Cl | 3-OCH<sub>3</sub>,2-Cl |
A-1122 | 4-F | 3-OCH<sub>3</sub>,2-Cl |
A-1123 | 4-Br | 3-OCH<sub>3</sub>,2-Cl |
A-1124 | 4-OCH<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1125 | 4-CF<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1126 | 4-C<sub>6</sub>H<sub>5</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1127 | 4-CH<sub>3</sub> | 3-OCH<sub>3</sub>,2-Cl |
A-1128 | - | 4-OCH<sub>3</sub>,3-Cl |
A-1129 | 2-Cl | 4-OCH<sub>3</sub>,3-Cl |
A-1130 | 2-F | 4-OCH<sub>3</sub>,3-Cl |
A-1131 | 2-Br | 4-OCH<sub>3</sub>,3-Cl |
A-1132 | 2-OCH<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1133 | 2-CF<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1134 | 2-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1135 | 2-CH<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1136 | 3-Cl | 4-OCH<sub>3</sub>,3-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1137 | 3-F | 4-OCH<sub>3</sub>,3-Cl |
A-1138 | 3-Br | 4-OCH<sub>3</sub>,3-Cl |
A-1139 | 3-OCH<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1140 | 3-CF<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1141 | 3-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1142 | 3-CH<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1143 | 4-Cl | 4-OCH<sub>3</sub>,3-Cl |
A-1144 | 4-F | 4-OCH<sub>3</sub>,3-Cl |
A-1145 | 4-Br | 4-OCH<sub>3</sub>,3-Cl |
A-1146 | 4-OCH<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1147 | 4-CF<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1148 | 4-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1149 | 4-CH<sub>3</sub> | 4-OCH<sub>3</sub>,3-Cl |
A-1150 | - | 4-OCH<sub>3</sub>,2-Cl |
A-1151 | 2-Cl | 4-OCH<sub>3</sub>,2-Cl |
A-1152 | 2-F | 4-OCH<sub>3</sub>,2-Cl |
A-1153 | 2-Br | 4-OCH<sub>3</sub>,2-Cl |
A-1154 | 2-OCH<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1155 | 2-CF<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1156 | 2-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1157 | 2-CH<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1158 | 3-Cl | 4-OCH<sub>3</sub>,2-Cl |
A-1159 | 3-F | 4-OCH<sub>3</sub>,2-Cl |
A-1160 | 3-Br | 4-OCH<sub>3</sub>,2-Cl |
A-1161 | 3-OCH<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1162 | 3-CF<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1163 | 3-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1164 | 3-CH<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1165 | 4-Cl | 4-OCH<sub>3</sub>,2-Cl |
A-1166 | 4-F | 4-OCH<sub>3</sub>,2-Cl |
A-1167 | 4-Br | 4-OCH<sub>3</sub>,2-Cl |
A-1168 | 4-OCH<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1169 | 4-CF<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1170 | 4-C<sub>6</sub>H<sub>5</sub> | 4-OCH<sub>3</sub>,2-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1171 | 4-CH<sub>3</sub> | 4-OCH<sub>3</sub>,2-Cl |
A-1172 | - | 2-OCH<sub>3</sub>,3-Cl |
A-1173 | 2-Cl | 2-OCH<sub>3</sub>,3-Cl |
A-1174 | 2-F | 2-OCH<sub>3</sub>,3-Cl |
A-1175 | 2-Br | 2-OCH<sub>3</sub>,3-Cl |
A-1176 | 2-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1177 | 2-CF<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1178 | 2-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1179 | 2-CH<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1180 | 3-Cl | 2-OCH<sub>3</sub>,3-Cl |
A-1181 | 3-F | 2-OCH<sub>3</sub>,3-Cl |
A-1182 | 3-Br | 2-OCH<sub>3</sub>,3-Cl |
A-1183 | 3-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1184 | 3-CF<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1185 | 3-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1186 | 3-CH<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1187 | 4-Cl | 2-OCH<sub>3</sub>,3-Cl |
A-1188 | 4-F | 2-OCH<sub>3</sub>,3-Cl |
A-1189 | 4-Br | 2-OCH<sub>3</sub>,3-Cl |
A-1190 | 4-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1191 | 4-CF<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1192 | 4-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1193 | 4-CH<sub>3</sub> | 2-OCH<sub>3</sub>,3-Cl |
A-1194 | - | 2-OCH<sub>3</sub>,4-Cl |
A-1195 | 2-Cl | 2-OCH<sub>3</sub>,4-Cl |
A-1196 | 2-F | 2-OCH<sub>3</sub>,4-Cl |
A-1197 | 2-Br | 2-OCH<sub>3</sub>,4-Cl |
A-1198 | 2-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1199 | 2-CF<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1200 | 2-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1201 | 2-CH<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1202 | 3-Cl | 2-OCH<sub>3</sub>,4-Cl |
A-1203 | 3-F | 2-OCH<sub>3</sub>,4-Cl |
A-1204 | 3-Br | 2-OCH<sub>3</sub>,4-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1205 | 3-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1206 | 3-CF<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1207 | 3-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1208 | 3-CH<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1209 | 4-Cl | 2-OCH<sub>3</sub>,4-Cl |
A-1210 | 4-F | 2-OCH<sub>3</sub>,4-Cl |
A-1211 | 4-Br | 2-OCH<sub>3</sub>,4-Cl |
A-1212 | 4-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1213 | 4-CF<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1214 | 4-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1215 | 4-CH<sub>3</sub> | 2-OCH<sub>3</sub>,4-Cl |
A-1216 | - | 2-OCH<sub>3</sub>,5-Cl |
A-1217 | 2-Cl | 2-OCH<sub>3</sub>,5-Cl |
A-1218 | 2-F | 2-OCH<sub>3</sub>,5-Cl |
A-1219 | 2-Br | 2-OCH<sub>3</sub>,5-Cl |
A-1220 | 2-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1221 | 2-CF<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1222 | 2-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1223 | 2-CH<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1224 | 3-Cl | 2-OCH<sub>3</sub>,5-Cl |
A-1225 | 3-F | 2-OCH<sub>3</sub>,5-Cl |
A-1226 | 3-Br | 2-OCH<sub>3</sub>,5-Cl |
A-1227 | 3-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1228 | 3-CF<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1229 | 3-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1230 | 3-CH<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1231 | 4-Cl | 2-OCH<sub>3</sub>,5-Cl |
A-1232 | 4-F | 2-OCH<sub>3</sub>,5-Cl |
A-1233 | 4-Br | 2-OCH<sub>3</sub>,5-Cl |
A-1234 | 4-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1235 | 4-CF<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1236 | 4-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1237 | 4-CH<sub>3</sub> | 2-OCH<sub>3</sub>,5-Cl |
A-1238 | - | 2-OCH<sub>3</sub>,6-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1239 | 2-Cl | 2-OCH<sub>3</sub>,6-Cl |
A-1240 | 2-F | 2-OCH<sub>3</sub>,6-Cl |
A-1241 | 2-Br | 2-OCH<sub>3</sub>,6-Cl |
A-1242 | 2-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1243 | 2-CF<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1244 | 2-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1245 | 2-CH<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1246 | 3-Cl | 2-OCH<sub>3</sub>,6-Cl |
A-1247 | 3-F | 2-OCH<sub>3</sub>,6-Cl |
A-1248 | 3-Br | 2-OCH<sub>3</sub>,6-Cl |
A-1249 | 3-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1250 | 3-CF<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1251 | 3-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1252 | 3-CH<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1253 | 4-Cl | 2-OCH<sub>3</sub>,6-Cl |
A-1254 | 4-F | 2-OCH<sub>3</sub>,6-Cl |
A-1255 | 4-Br | 2-OCH<sub>3</sub>,6-Cl |
A-1256 | 4-OCH<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1257 | 4-CF<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1258 | 4-C<sub>6</sub>H<sub>5</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1259 | 4-CH<sub>3</sub> | 2-OCH<sub>3</sub>,6-Cl |
A-1260 | - | 2-Cl,5-Cl |
A-1261 | 2-Cl | 2-Cl,5-Cl |
A-1262 | 2-F | 2-Cl,5-Cl |
A-1263 | 2-Br | 2-Cl,5-Cl |
A-1264 | 2-OCH<sub>3</sub> | 2-Cl,5-Cl |
A-1265 | 2-CF<sub>3</sub> | 2-Cl,5-Cl |
A-1266 | 2-C<sub>6</sub>H<sub>5</sub> | 2-Cl,5-Cl |
A-1267 | 2-CH<sub>3</sub> | 2-Cl,5-Cl |
A-1268 | 3-Cl | 2-Cl,5-Cl |
A-1269 | 3-F | 2-Cl,5-Cl |
A-1270 | 3-Br | 2-Cl,5-Cl |
A-1271 | 3-OCH<sub>3</sub> | 2-Cl,5-Cl |
A-1272 | 3-CF<sub>3</sub> | 2-Cl,5-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1273 | 3-C<sub>6</sub>H<sub>5</sub> | 2-Cl,5-Cl |
A-1274 | 3-CH<sub>3</sub> | 2-Cl,5-Cl |
A-1275 | 4-Cl | 2-Cl,5-Cl |
A-1276 | 4-F | 2-Cl,5-Cl |
A-1277 | 4-Br | 2-Cl,5-Cl |
A-1278 | 4-OCH<sub>3</sub> | 2-Cl,5-Cl |
A-1279 | 4-CF<sub>3</sub> | 2-Cl,5-Cl |
A-1280 | 4-C<sub>6</sub>H<sub>5</sub> | 2-Cl,5-Cl |
A-1281 | 4-CH<sub>3</sub> | 2-Cl,5-Cl |
A-1282 | - | 2-Cl,4-Cl |
A-1283 | 2-Cl | 2-Cl,4-Cl |
A-1284 | 2-F | 2-Cl,4-Cl |
A-1285 | 2-Br | 2-Cl,4-Cl |
A-1286 | 2-OCH<sub>3</sub> | 2-Cl,4-Cl |
A-1287 | 2-CF<sub>3</sub> | 2-Cl,4-Cl |
A-1288 | 2-C<sub>6</sub>H<sub>5</sub> | 2-Cl,4-Cl |
A-1289 | 2-CH<sub>3</sub> | 2-Cl,4-Cl |
A-1290 | 3-Cl | 2-Cl,4-Cl |
A-1291 | 3-F | 2-Cl,4-Cl |
A-1292 | 3-Br | 2-Cl,4-Cl |
A-1293 | 3-OCH<sub>3</sub> | 2-Cl,4-Cl |
A-1294 | 3-CF<sub>3</sub> | 2-Cl,4-Cl |
A-1295 | 3-C<sub>6</sub>H<sub>5</sub> | 2-Cl,4-Cl |
A-1296 | 3-CH<sub>3</sub> | 2-Cl,4-Cl |
A-1297 | 4-Cl | 2-Cl,4-Cl |
A-1298 | 4-F | 2-Cl,4-Cl |
A-1299 | 4-Br | 2-Cl,4-Cl |
A-1300 | 4-OCH<sub>3</sub> | 2-Cl,4-Cl |
A-1301 | 4-CF<sub>3</sub> | 2-Cl,4-Cl |
A-1302 | 4-C<sub>6</sub>H<sub>5</sub> | 2-Cl,4-Cl |
A-1303 | 4-CH<sub>3</sub> | 2-Cl,4-Cl |
A-1304 | - | 2-Cl,3-Cl |
A-1305 | 2-Cl | 2-Cl,3-Cl |
A-1306 | 2-F | 2-Cl,3-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1307 | 2-Br | 2-Cl,3-Cl |
A-1308 | 2-OCH<sub>3</sub> | 2-Cl,3-Cl |
A-1309 | 2-CF<sub>3</sub> | 2-Cl,3-Cl |
A-1310 | 2-C<sub>6</sub>H<sub>5</sub> | 2-Cl,3-Cl |
A-1311 | 2-CH<sub>3</sub> | 2-Cl,3-Cl |
A-1312 | 3-Cl | 2-Cl,3-Cl |
A-1313 | 3-F | 2-Cl,3-Cl |
A-1314 | 3-Br | 2-Cl,3-Cl |
A-1315 | 3-OCH<sub>3</sub> | 2-Cl,3-Cl |
A-1316 | 3-CF<sub>3</sub> | 2-Cl,3-Cl |
A-1317 | 3-C<sub>6</sub>H<sub>5</sub> | 2-Cl,3-Cl |
A-1318 | 3-CH<sub>3</sub> | 2-Cl,3-Cl |
A-1319 | 4-Cl | 2-Cl,3-Cl |
A-1320 | 4-F | 2-Cl,3-Cl |
A-1321 | 4-Br | 2-Cl,3-Cl |
A-1322 | 4-OCH<sub>3</sub> | 2-Cl,3-Cl |
A-1323 | 4-CF<sub>3</sub> | 2-Cl,3-Cl |
A-1324 | 4-C<sub>6</sub>H<sub>5</sub> | 2-Cl,3-Cl |
A-1325 | 4-CH<sub>3</sub> | 2-Cl,3-Cl |
A-1326 | - | 2-Cl,6-Cl |
A-1327 | 2-Cl | 2-Cl,6-Cl |
A-1328 | 2-F | 2-Cl,6-Cl |
A-1329 | 2-Br | 2-Cl,6-Cl |
A-1330 | 2-OCH<sub>3</sub> | 2-Cl,6-Cl |
A-1331 | 2-CF<sub>3</sub> | 2-Cl,6-Cl |
A-1332 | 2-C<sub>6</sub>H<sub>5</sub> | 2-Cl,6-Cl |
A-1333 | 2-CH<sub>3</sub> | 2-Cl,6-Cl |
A-1334 | 3-Cl | 2-Cl,6-Cl |
A-1335 | 3-F | 2-Cl,6-Cl |
A-1336 | 3-Br | 2-Cl,6-Cl |
A-1337 | 3-OCH<sub>3</sub> | 2-Cl,6-Cl |
A-1338 | 3-CF<sub>3</sub> | 2-Cl,6-Cl |
A-1339 | 3-C<sub>6</sub>H<sub>5</sub> | 2-Cl,6-Cl |
A-1340 | 3-CH<sub>3</sub> | 2-Cl,6-Cl |
(R<sup>1</sup>)<sub>n</sub> | (R<sup>2</sup>)<sub>m</sub> | |
A-1341 | 4-Cl | 2-Cl,6-Cl |
A-1342 | 4-F | 2-Cl,6-Cl |
A-1343 | 4-Br | 2-Cl,6-Cl |
A-1344 | 4-OCH<sub>3</sub> | 2-Cl,6-Cl |
A-1345 | 4-CF<sub>3</sub> | 2-Cl,6-Cl |
A-1346 | 4-C<sub>6</sub>H<sub>5</sub> | 2-Cl,6-Cl |
A-1347 | 4-CH<sub>3</sub> | 2-Cl,6-Cl |
在式I化合物中,优选下列式I-B化合物,其中式I中的A为基团A2,其中X为S且其中变量n、m、R1和R2具有上面所给的含义。
这些化合物的实例是其中(R1)n和(R2)m具有表A的每一行所给含义的那些(化合物I-B.1至I-B.1347)。
在式I化合物中,还优选下列式I-C化合物,其中式I中的A为基团A1,其中X为O且R6为CH3以及其中变量n、m、R1和R2具有上面所给的含义。
这些化合物的实例是其中(R1)n和(R2)m具有表A的每一行所给含义的那些(化合物I-C.1至I-C.1347)。
在式I化合物中,还优选下列式I-D化合物,其中式I中的A为基团A1,其中X为S且R6为CH3以及其中变量n、m、R1和R2具有上面所给的含义。
这些化合物的实例是其中(R1)n和(R2)m具有表A的每一行所给含义的那些(化合物I-D.1至I-D.1347)。
在式I化合物中,还优选下式I-E、I-F、I-G、I-H、I-J、I-K、I-L和I-M化合物,其中变量n、m、R1和R2具有上面所给的含义。
这些化合物的实例是其中(R1)n和(R2)m具有表A的每一行所给含义的那些(化合物I-E.1至I-E.1347、I-F.1至I-F.1347、I-G.1至I-G.1347、I-H.1至I-H.1347、I-J.1至I-J.1347、I-K.1至I-K.1347、I-L.1至I-L.1347和I-M.1至I-M.1347)。
本发明化合物例如可以由对应的二苯基乙基胺II通过方案1和2中所列合成途径制备。其中A为基团A2(其中X为S且R7为H)的式I化合物可以根据方案1中所列方法得到:
方案1:
根据方案1中所列方法,通过常规方式,例如通过使1,2-二苯基氨基乙烷II与硫光气反应而将II转化成对应的异硫氰酸酯III(例如参见Houben-Weyl,E4,“有机化学方法”,第IIIc章,第837-842页)。然后使异硫氰酸酯III与通式IV的氨基乙醇反应,从而得到式V的硫脲化合物。氨基乙醇IV与异硫氰酸酯III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式环化,从而得到所需式I的噻唑啉化合物,其中A为A2,其中X为S且R7为H。化合物V的环化例如可以在酸催化下或在脱水条件下通过例如Mitsunobu反应而进行(参见Tetrahedron Letters 1999,40,3125-3128)。
其中A为基团A2(其中X为O且R7为H)的式I化合物可以通过类似于方案1所列方法的途径而得到(还参见Pestic.Biochem.Physiol.1988,30,190-197)。与方案1的方法不同的是,例如通过与光气、双光气或另一光气等价物反应将二苯基氨基乙烷II转化成对应的异氰酸酯IIIa。然后使异氰酸酯IIIa与氨基乙醇IV反应并环化如此得到的脲。
其中A为式A2的基团(其中X为O且R7为H)的式I化合物还可以通过方案2所列方法得到。在方案2中,变量Hal为卤素,尤其是氯。Y为OH或卤素。Z为氢、烷基或卤素,尤其是氟。
根据方案2,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转化成对应的式VII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VII与氨基醇IV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Va的2-羟基乙基脲{Y=OH}。可以根据Org.Lett.1999,1,1705-1708或TetrahedronLett.1992,33,2807-2810中所述的程序将2-羟基乙基脲环化成噁唑啉化合物I。
或者可以根据Bioorg.Med.Chem.Lett.1994,4,2317-2322中所述的方法或在下述条件下环化取代的2-氯乙基脲Va{X=Cl}。氯乙基脲Va可以由对应的二苯基乙基胺II通过与异氰酸2-氯乙基酯VIII反应而得到。
其中式I中的A为基团A1(其中R6不为氢)或基团A2(其中R7不为氢)的式I化合物可以由带有R6(或R7)的式I化合物作为原料而得到。
为了得到其中R6或R7为C1-C6烷基或烷基C1-C6烷基羰基的式I化合物,使原料与合适的烷基化或酰基化试剂Ra-L反应,其中L为离去基团如卤素且Ra为C1-C6烷基或烷基C1-C6烷基羰基。该反应可以通过在有关有机合成的标准教科书中描述的常规方法进行,例如参见J.March,Advanced Organic Synthesis,第3版,John Wiley and Sons。
为了得到其中R6或R7为C1-C6烷氧羰基或C1-C6烷硫基羰基的式I化合物,使原料与与合适的式Rb-C(O)-Hal的卤代甲酸酯反应,其中Hal为卤素,尤其是氯且其中Rb为C1-C6烷氧基或C1-C6烷硫基。该反应可以通过在有关有机合成的标准教科书中描述的常规方法进行,例如参见J.March,Advanced Organic Synthesis,第3版,John Wiley and Sons。
氰基可以通过例如使原料与溴化氰根据本申请试验部分中所述的方法反应作为基团R6或R7引入。硝基作为基团R6或R7的引入可以通过使其中R6或R7为H的化合物I与硝鎓源根据本领域众所周知的标准方法反应而进行。
例如可以通过使原料与氯磺酰胺Cl-(SO2)aRb根据有关有机合成的标准教科书中描述的常规方法反应而将基团(SO2)aRb作为基团R6或R7引入,例如参见J.March,Advanced Organic Synthesis,第3版,John Wileyand Sons。
例如可以通过使原料与氯甲酰胺Cl-CO-NRaRb反应或对于Rb为氢,与异氰酸酯OCN-Ra反应而将基团C(O)NRaRb作为基团R6或R7引入。
式II的二苯基乙基胺在本领域是已知的(例如1,2-二苯基乙基胺,CAS号3082-58-4)或它们可以通过有机化学家熟悉的且在本领域众所周知的方法制备。制备二苯基乙基胺II的合适方法尤其包括还原性胺化对应的苯基苄基酮或还原对应的苯基苄基肟(例如参见J.Med.Chem.1995,38,1600-1607;J.Med.Chem 1994,37(7),913-923)。式II的二苯基乙基胺还可以根据Tetrahedron,1999,55,第8883-8904页中所描述的方法通过将苯基-或苄基-有机金属试剂加成于合适的亚胺如苯甲醛或2-苯基乙醛化合物的叔丁基亚磺酰基亚胺上而制备。
2-氨基乙醇化合物IV和异氰酸2-氨基乙基酯VIII可以市购或可以根据有机化学家熟悉的常规方法制备。
由于通式I化合物具有优异的活性,它们可以用于防治选自有害昆虫、蜘蛛和线虫的动物害虫。因此,本发明进一步提供了用于防治该类动物害虫的农用组合物,包含具有杀虫作用的量的至少一种通式I化合物或至少一种I的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通式I的活性化合物或几种本发明活性化合物I的混合物。本发明的组合物可以包含单一异构体或异构体混合物或单一互变异构体或互变异构体混合物。
式I化合物和包含它们的杀虫组合物是对防治选自昆虫、蜘蛛和线虫的动物害虫有效的试剂。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)、Diabrotica longicornis、Diabrotica 12-punctata、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(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(Glossma 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 cerasi)、苹果实蝇(Rhagoletis pomonella)、Tabanus bovinus、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)、桔硬蓟马(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 geminata)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)、Euschistus impictiventris、棉红铃喙缘蝽(Leptoglossusphyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubea insularis和Thyanta perditor;
同翅目昆虫(同翅目(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 ribis-nigri、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 femur-rubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲蟑螂(Periplaneta americana)、美洲沙漠蝗(Schistocerca americana)、Schistocerca peregrina、Stauronotus maroccanus和庭疾灶螽(Tachycinesasynamorus),
蜘蛛纲(Arachnoidea),例如蜘蛛(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(Amblyomma americanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilusdecoloratus、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(Dermanyssusgallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),瘿螨属(Eriophyidae spp.)如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyessheldoni;细螨属(Tarsonemidae spp.)如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨属(Tenuipalpidae spp.)如紫红短须螨(Brevipalpus phoenicis);叶螨属(Tetranychidae spp.)如朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychuscitri)和oligonychus pratensis;
蚤目(Siphonaptera),例如Xenopsylla cheopsis、角叶(Ceratophyllus)属。
线虫,包括植物寄生线虫和生活在土壤中的线虫。
植物寄生线虫包括作为根结线虫的北方根结线虫(Meloidogynehapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogynejavanica)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(Bursaphelenchusxylophilus)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(Ditylenchusdestructor)、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,Longidorus elongatus和其他长针线虫属(Longidorus);射针线虫,短针线虫属(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(Radopholus similis)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,Trichodorus primitivus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、鞘翅目和同翅目昆虫以及蜱螨目蜘蛛。本发明式I化合物对防治鳞翅目和同翅目昆虫特别有用。
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免受动物害虫,尤其是昆虫、螨虫或蜘蛛的损害。术语“作物”指生长的作物和收获的作物。
可以通过本领域已知的任何施用方法使动物害虫,即昆虫、蜘蛛和线虫,植物,植物在其中生长的土壤或水与本发明化合物I或含有它们的组合物接触。“接触”包括直接接触(直接将化合物/组合物施用于动物害虫或植物-通常是植物的叶、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生长场所)。
此外,动物害虫可以通过使目标害虫、其食物源或其生长场所与杀虫有效量的式(I)化合物接触而防治。施用可以在生长场所、生长作物或收获作物被害虫侵染之前或之后进行。
“生长场所”是指栖息地,繁殖地,害虫或寄生虫生长或可能生长的植物、种子、土壤、区域、材料或环境。
适用于本发明方法中的有效量可以根据特定的式I化合物、目标害虫、施用方法、施用时间、气候条件、动物害虫习性等而变化。通常而言,对于在处理作物植物中的应用,本发明化合物I和/或组合物的施用率可以为约0.1-4000g/ha,理想的是约25-600g/ha,更理想的是约50-500g/ha。对于在处理种子中的应用,典型施用率为约1-500g/kg种子,理想的是约2-300g/kg种子,更理想的是约10-200g/kg种子。在保护材料中的常规施用率例如为约0.001-2000g,理想的是约0.005-1000g活性化合物/m3处理材料。
化合物I或包含它们的杀虫组合物例如可以溶液、乳液、微乳液、悬浮液、可流动浓缩物、粉剂、粉末、糊和颗粒形式使用。使用形式取决于特定的目的;在任何情况下应保证本发明化合物精细和均匀地分布。
用于防治动物害虫,即昆虫、蜘蛛或线虫的杀虫组合物含有这样量的至少一种通式I的化合物或I的可农用盐和常用于配制杀虫组合物的助剂。
配制剂以已知方式制备,例如通过将活性成分与溶剂和/或载体混合来制备,需要的话使用乳化剂和分散剂,若使用水作为稀释剂,则还可以使用其它有机溶剂作为辅助溶剂。适合的助剂主要是:溶剂如芳族化合物(如二甲苯),氯代芳族化合物(如氯苯),链烷烃(如矿物油馏分),醇(如甲醇、丁醇),酮(如环己酮),胺(如乙醇胺、二甲基甲酰胺)和水;载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐以及脂肪酸及其碱金属和碱土金属盐,硫酸化脂肪醇乙二醇醚的盐,磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚或甲醛的缩合物,聚氧乙烯辛基苯基醚,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,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备直接可喷溶液、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,例如苯、甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,甲醇,乙醇,丙醇,丁醇,氯仿,四氯化碳,环己醇,环己酮,氯苯,异佛尔酮,强极性溶剂,例如二甲基甲酰胺、二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和粉剂可以通过将活性物质与固体载体混合或一起研磨而制备。
颗粒如涂覆颗粒、压实颗粒、浸渍颗粒和均质颗粒可以通过将活性成分与固体载体粘附而制备。固体载体的实例是矿土如硅石、硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、尿素;以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉;纤维素粉和其它固体载体。
本发明的该类配制剂或组合物包括本发明的式I化合物(或其结合)以及与其相混合的一种或多种可农用惰性固体或液体载体。这些组合物含有杀虫有效量的所述化合物,该量可以取决于特定化合物、目标害虫和使用方法而变化。
通常而言,配制剂包含0.01-95重量%,优选0.1-90重量%的活性成分。活性成分以90-100%,优选95-100%的纯度(根据NMR波谱)使用。
示例性配制剂如下所述:
I.5重量份本发明化合物与95重量份细碎高岭土均匀混合。得到包含5重量%活性成分的粉剂。
II.将30重量份本发明化合物与由92重量份粉状硅胶和8重量份已经喷雾到该硅胶表面上的石蜡油组成的混合物均匀混合。得到具有良好粘附性能的活性成分配制剂(包含23重量%活性成分)。
III.将10重量份本发明化合物溶于由90重量份二甲苯、6重量份的8-10摩尔氧化乙烯与1摩尔油酸N-单乙醇酰胺的加合物、2重量份十二烷基苯磺酸钙和2重量份的40摩尔氧化乙烯与1摩尔蓖麻油的加合物组成的混合物中(包含9重量%活性成分)。
IV.将20重量份本发明化合物溶于由60重量份环己酮、30重量份异丁醇、5重量份的7摩尔氧化乙烯与1摩尔异辛基酚的加合物和5重量份的40摩尔氧化乙烯与1摩尔蓖麻油的加合物组成的混合物中(包含16重量%活性成分)。
V.将80重量份本发明化合物与3重量份二异丁基萘-α-磺酸钠、10重量份来自亚硫酸盐废液的木素磺酸的钠盐和7重量份粉状硅胶彻底混合并将该混合物在锤磨机中研磨(包含80重量%活性成分)。
VI.将90重量份本发明化合物与10重量份N-甲基-α-吡咯烷酮混合,得到适于以微滴形式使用的溶液(包含90重量%活性成分)。
VII.将20重量份本发明化合物溶于由40重量份环己酮、30重量份异丁醇、20重量份的7摩尔氧化乙烯与1摩尔异辛基苯酚的加合物和10重量份的40摩尔氧化乙烯与1摩尔蓖麻油的加合物组成的混合物中。将该溶液倾入100,000重量份水中并在其中精细分布,得到包含0.02重量%活性成分的水分散体。
VIII.将20重量份本发明化合物与3重量份二异丁基萘-α-磺酸钠、17重量份来自亚硫酸盐废液的木素磺酸的钠盐和60重量份粉状硅胶彻底混合,并将混合物在锤磨机中研磨。将该混合物在20,000重量份水中精细分布,得到包含0.1重量%活性成分的喷雾混合物。
活性成分可以通过喷雾、雾化、撒粉、撒播或浇灌直接使用,以其配制剂形式或由其制备的使用形式使用,例如以直接可喷溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、粉剂、撒播用材料或颗粒形式使用。使用形式完全取决于意欲的目的;在任何情况下都应确保本发明的活性成分尽可能最佳地分布。
含水使用形式可以通过添加水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为了制备乳液、糊或油分散体,可以通过湿润剂、增粘剂、分散剂或乳化剂将物质直接或溶于油或溶剂之后在水中均化。另外,可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话,溶剂或油组成的浓缩物且该类浓缩物适于用水稀释。
活性成分在即用产品中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性成分还可成功地用于超低容量方法(ULV),其中可以施用包含超过95重量%活性成分的配制剂或甚至可以在没有添加剂的情况下施用活性成分。
根据本发明使用的组合物还可以含有其他活性成分,例如其他杀虫剂、杀昆虫剂、除草剂、杀真菌剂、其他杀虫剂或杀菌剂,肥料如硝酸铵、尿素、钾碱和酸性磷酸盐,植物毒素和植物生长调节剂,安全剂和杀线虫剂。这些额外的成分可以顺序使用或与上述组合物结合使用,合适的话还可以在紧临使用之前加入(桶混合)。例如,可以在用其他活性成分处理之前或之后用本发明的组合物喷雾植物。
这些试剂可以与本发明所用试剂以1∶10至10∶1的重量比混合。将作为杀虫剂使用的化合物I或包含它们的组合物与其他杀虫剂混合通常导致更宽的杀虫作用谱。
下列式I化合物可以与其一起使用的杀虫剂用来阐述可能的组合,而不施以任何限制:
有机磷酸酯类:高灭磷(Acephate)、谷硫磷(Azinphos-methyl)、毒死蜱(Chlorpyrifos)、毒虫畏(Chlorfenvinphos)、二嗪农(Diazinon)、敌敌畏(Dichlorvos)、百治磷(Dicrotophos)、乐果(Dimethoate)、乙拌磷(Disulfoton)、乙硫磷(Ethion)、杀螟松(Fenitrothion)、倍硫磷(Fenthion)、异噁唑磷(Isoxathion)、马拉硫磷(Malathion)、甲胺磷(Methamidophos)、杀扑磷(Methidathion)、甲基一六零五(Methyl-Parathion)、速灭磷(Mevinphos)、久效磷(Monocrotophos)、砜吸磷(Oxydemeton-methyl)、对氧磷(Paraoxon)、一六零五(Parathion)、稻丰散(Phenthoate)、伏杀磷(Phosalone)、亚胺硫磷(Phosmet)、磷胺(Phosphamidon)、甲拌磷(Phorate)、辛硫磷(Phoxim)、虫螨磷(Pirimiphos-methyl)、丙溴磷(Profenofos)、丙硫磷(Prothiofos)、乙丙硫磷(Sulprophos)、三唑磷(Triazophos)、敌百虫(Trichlorfon);
氨基甲酸酯类:棉铃威(Alanycarb)、丙硫克百威(Benfuracarb)、甲萘威(Carbaryl)、丁硫克百威(Carbosulfan)、双氧威(Fenoxycarb)、呋线威(Furathiocarb)、噁二唑虫(Indoxacarb)、灭虫威(Methiocarb)、灭多虫(Methomyl)、甲氨叉威(Oxamyl)、抗蚜威(Pirimicarb)、残杀威(Propoxur)、硫双威(Thiodicarb)、唑蚜威(Triazamate);
合成除虫菊酯类:氟氯菊酯(Bifenthrin)、氟氯氰菊酯(Cyfluthrin)、氯氰菊酯(Cypermethrin)、溴氰菊酯(Deltamethrin)、高氰戊菊酯(Esfenvalerate)、醚菊酯(Ethofenprox)、甲氰菊酯(Fenpropathrin)、杀灭菊酯(Fenvalerate)、(RS)氯氟氰菊酯(Cyhalothrin)、氯氟氰菊酯(Lambda-Cyhalothrin)、氯菊酯(Permethrin)、灭虫硅醚(Silafluofen)、氟胺氰菊酯(Tau-Fluvalinate)、七氟菊酯(Tefluthrin)、四溴菊酯(Tralomethrin)、己体氯氰菊酯(Zeta-Cypermethrin);
节肢动物生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类:定虫隆(Chlorfluazuron)、氟脲杀(Diflubenzuron)、氟螨脲(Flucycloxuron)、氟虫脲(Flufenoxuron)、氟铃脲(Hexaflumuron)、氟丙氧脲(Lufenuron)、双苯氟脲(Novaluron)、伏虫隆(Teflubenzuron)、杀虫隆(Triflumuron);噻嗪酮(Buprofezin)、噁茂醚(Diofenolan)、噻螨酮(Hexythiazox)、特苯噁唑(Etoxazole)、四螨嗪(Clofentazine);b)蜕皮激素拮抗剂:特丁苯酰肼(Halofenozide)、甲氧苯酰肼(Methoxyfenozide)、双苯酰肼(Tebufenozide);c)保幼激素类似物:蚊蝇醚(Pyriproxyfen)、蒙五一五(Methoprene)、双氧威(Fenoxycarb);d)类脂生物合成抑制剂:螺螨酯(Spirodiclofen);
各种其它杀虫剂:齐墩螨素(Abamectin)、灭螨醌(Acequinocyl)、虫螨脒(Amitraz)、艾扎丁(Azadirachtin)、联苯肼酯(Bifenazate)、杀螟丹(Cartap)、氟唑虫清(Chlorfenapyr)、杀虫脒(Chlordimeform)、灭蝇胺(Cyromazine)、杀螨硫隆(Diafenthiuron)、呋虫胺(Dinetofuran)、噁茂醚(Diofenolan)、埃玛菌素(Emamectin)、硫丹(Endosulfan)、Ethiprole、喹螨醚(Fenazaquin)、锐劲特(Fipronil)、伐虫脒(Formetanate)、伐虫脒盐酸盐(Formetanatehydrochloride)、灭蚁腙(Hydramethylnon)、吡虫啉(Imidacloprid)、噁二唑虫(Indoxacarb)、哒螨酮(Pyridaben)、拒嗪酮(Pymetrozine)、艾克敌105(Spinosad)、硫(Sulfur)、吡螨胺(Tebufenpyrad)、噻虫嗪(Thiamethoxam)和硫环杀(Thiocyclam)。
现在通过下列实施例更详细描述本发明。
本发明化合物以及中间体通过偶合高效液相色谱法/质谱法(HPLC/MS)、NMR或其熔点表征。HPLC柱:RP-18柱(Chromolith SpeedROD,购自德国Merck KgaA)。洗脱:比例为5∶95-95∶5的乙腈+0.1%三氟乙酸(TFA)/水+0.1%TFA,40℃下5分钟。MS Quadrupol电喷射离子化,80V(正模式)。
1.制备实施例
实施例1:(4,5-二氢-4-甲基噁唑-2-基)-[2-(3-氯苯基)-1-苯基乙基]胺1.11-(2-(3-氯苯基)-1-苯基-乙基)-3-(2-氯-丙基)脲
在0℃下在4小时内将THF中的72mg(0.6mmol)异氰酸2-氯丙基酯分4批加入在2ml THF中的116mg(0.5mmol)2-(3-氯苯基)-1-苯基-乙基胺中。将该溶液在室温下搅拌过夜。在蒸发溶剂并含水处理之后得到128mg(0.36mmol,73%)所需脲。
1.2(4,5-二氢-4-甲基噁唑-2-基)-[2-(3-氯-苯基)-1-苯基乙基]胺将158mg(0.45mmol)1-(2-(3-氯苯基)-1-苯基-乙基)-3-(2-氯丙基)脲和386mg(0.9mmol)1,5,7-三氮杂双环[4.4.0]癸-5-烯-7-甲基聚苯乙烯(TBD-甲基聚苯乙烯,Novabiochem)在1,4-二噁烷中加热到100℃,持续12小时。在通过过滤除去聚合物并蒸发溶剂之后得到92mg(0.31mmol,69%)所需氨基噁唑啉。
实施例2:(4,5-二氢噁唑-2-基)-[2-(4-氟-苯基)-1-苯基-乙基]胺
在0℃下用异氰酸2-氯乙基酯(0.89g)滴加处理2-(4-氟-苯基)-1-苯基-乙基胺(1.50g)的THF溶液。在室温下搅拌过夜后蒸发溶剂并将残余物溶于二甲氧基乙烷(25ml)中。加入DBU(1,8-二氮杂双环[5.4.0]十一碳-7-烯(1.78g)并将反应混合物在回流下加热1小时。在二氧化硅上的柱层析得到1.3g标题化合物。
实施例3:[1-(4-氯苯基)-2-苯基-乙基]-(4,5-二氢噻唑-2-基)胺
3.11-(4-氯苯基)-2-苯基-乙基胺
向高压釜(300ml,hasteloi)中加入1-(4-氯苯基)-2-苯基乙酮(22g)、四氢呋喃(90ml)、钴活化的阮内镍(5g)和氨(45g)。将该高压釜用氮气冲扫并加热到70℃。在该温度下加入氢气至压力为150巴,将反应温度升至110℃。在搅拌过夜之后将反应混合物滤过二氧化硅并用THF洗涤。含水处理并萃取到二氯甲烷中以83%的产率得到纯胺。
3.21-氯-4-(1-异硫氰酸酯基-1-苯基乙烷-2-基)苯
将1-(4-氯苯基)-2-苯基乙基胺(4.86g)加入硫光气(2.88g)在二氯甲烷(40ml)、碳酸钾(8.56g)和水(10ml)中的混合物中。将该混合物搅拌过夜。然后将反应混合物倾入水中并用二氯甲烷萃取水相,得到5.67g(99%)异硫氰酸酯化合物。
3.31-[1-(4-氯苯基)-2-苯基乙基]-3-(2-羟基乙基)硫脲
将1-氯-4-(1-异硫氰酸酯基-2-苯基乙基)苯(0.50g)在氯仿(30ml)中的溶液用乙醇胺(0.11g)处理并在室温下搅拌过夜。在二氧化硅上层析得到产物(0.30g)。
3.4[1-(4-氯苯基)-2-苯基-乙基]-(4,5-二氢噻唑-2-基)胺
将1-[1-(4-氯苯基)-2-苯基-乙基]-3-(2-羟基乙基)硫脲(0.30g)与浓盐酸一起回流并在室温下继续搅拌过夜。通过倾析从所得油中除去盐酸相。将残余物溶于乙酸乙酯并用碳酸钾水溶液和水洗涤有机相。在干燥并蒸发溶剂之后得到0.14g 1-[1-(4-氯苯基)-2-苯基-乙基]-(4,5-二氢噻唑-2-基)胺。可以相应地制备通式Ia的化合物(实施例4-44)。这些化合物的光谱数据列于表1中。
实施例45:2-[2-(3-氯苯基)-1-苯基乙基亚氨基]噻唑烷-3-甲酸甲酯
在室温下将1-[2-(3-氯苯基)-2-苯基-乙基]-(4,5-二氢噻唑-2-基)胺(0.50g)、碳酸钾(0.33g)、二甲基甲酰胺(10ml)和2-3滴三乙基胺的混合物用氯甲酸甲酯(0.18g)处理并搅拌过夜。用水稀释并萃取到叔丁基甲基醚中得到粗产物,通过在二氧化硅上的柱层析将其提纯,得到[2-(3-氯苯基)-1-苯基乙基亚氨基]噻唑烷-3-甲酸甲酯(0.25g)。
实施例46:2-[2-(3-氯苯基)-1-苯基乙基亚氨基]噻唑烷-3-甲腈
在室温下将1-[1-(4-氯苯基)-2-苯基-乙基]-(4,5-二氢噻唑-2-基)胺(0.50g)、碳酸钾(0.33g)、二甲基甲酰胺(10ml)和2-3滴三乙基胺的混合物用溴化氰处理并搅拌过夜,然后在50℃下搅拌3小时。加入水并将反应混合物用甲基叔丁基醚萃取。在干燥之后蒸发溶剂并将残余物在硅胶上进行层析,得到19%腈。
相应地制备通式Ib化合物(实施例47-49)。这些化合物的光谱数据列于表2中。
表2:
实施例 | (R<sup>1</sup>)<sub>m</sub> | (R<sup>2</sup>)<sub>n</sub> | R<sup>6</sup> | X | 理化数据(熔点[℃];<sup>1</sup>H-NMR(CDCl<sub>3</sub>):δ[ppm];HPLC-MS:RT[min],分子量 |
45 | 3-Cl | - | C(O)OCH<sub>3</sub> | S | 2.95-3.2(m),3.9(s),4.0(mc),4.25(mc),6.95-7.35(m) |
46 | 3-Cl | - | CN | S | 3.05(mc),3.20(mc),3.80(mc),4.15(mc),7.0-7.4(m) |
47 | - | - | C<sub>2</sub>H<sub>5</sub> | S | 1.0(mc),2.9-3.5(m),4.1(mc),7.0-7.3(m) |
48 | 3-Cl | - | C<sub>2</sub>H<sub>5</sub> | S | 1.15(t),3.0(mc),3.3-3.6(m),4.15(mc),6.9-7.4(m) |
49 | 3-F | - | CH<sub>3</sub> | O | 2,80(s),2.95(d),3.2(mc),3.9-4.1(m),4.75(mc),6.75-7.35(m) |
实施例 | (R<sup>1</sup>)<sub>m</sub> | (R<sup>2</sup>)<sub>n</sub> | R<sup>6</sup> | X | 理化数据(熔点[℃];<sup>1</sup>H-NMR(CDCl<sub>3</sub>):δ[ppm];HPLC-MS:RT[min],分子量 |
168 | 3-Cl | - | COOCH<sub>3</sub> | 0 | 358[M+H]+ |
2.对害虫的作用实施例
式I化合物对害虫的作用通过下列试验证实。
配制活性化合物:
a.为了测试对棉蚜(Aphis gossypii)、桃蚜(Myzus persieae)和豆蚜(Aphisfabae)的活性,将其配制成用100ppm(表面活性剂)修正的50∶50丙酮:水溶液,
b.为了测试对南部灰翅夜蛾(Spodoptera eridania)的活性,将其配制成在35%丙酮和水的混合物中的10.000ppm溶液,该溶液需要的话用水稀释。
在试验完成之后,在每种情况下测定与未处理对照相比化合物仍引起75-100%抑制或死亡率的最低浓度(极限或最小浓度)。
棉蚜(Aphisgossypii)
通过将侵染的叶片放于试验植物的顶部而用约100只实验室饲养的蚜虫侵染子叶阶段的棉花植物(品种为‘Delta Pine’)。24小时后移走叶片。将整个植物的子叶浸入试验化合物的梯度溶液中。5天后相对于对照植物上的死亡率确定处理植物上的蚜虫死亡率。
在该试验中,实施例14、18、19、24、25、26、29、35、36、41、42、43、45、51、52、53、61、64、70、79、82、83、100、101、114、118、123、124、131、132、133、134、135、142、144、147、150、155、159、162和163的化合物在300ppm下与未处理对照相比显示出超过80%的死亡率。
桃蚜(Myzus persicae)
通过将侵染的叶片放于测试植物的顶部而将第二对叶阶段的胡椒植物(品种为‘California Wonder’)用约40只实验室饲养的蚜虫侵染。24小时后移走叶片。将整个植物的叶子浸入试验化合物的梯度溶液中。5天后相对于对照植物上的死亡率确定处理植物上的蚜虫死亡率。
在该试验中,实施例5、6、7、14、15、16、18、19、23、24、25、26、27、29、30、33、34、35、36、38、41、42、43、44、45、46、49、51、52、54、56、63、70、71、76、78、81、83、91、98、99、101、102、103、108、115、119、122、125、130、132、136、137、141、144、156、157、160、161和164的化合物在300ppm下与未处理对照相比显示出超过80%的死亡率。
豆蚜(Aphis fabae)
通过将侵染的植物切片放于测试植物的顶部而将第一对叶阶段的旱金莲属植物(品种为‘Mixed Jewle’)用约25只实验室饲养的蚜虫侵染。24小时后移走植物切片。将测试植物的叶和茎浸入试验化合物的梯度溶液中。3天后测定蚜虫死亡率。
在该试验中,实施例6、66、93、146和162的化合物在300ppm下与未处理对照相比显示出超过80%的死亡率。
亚热带粘虫(南部灰翅夜蛾(Spodoptera eridania)),二龄幼虫
在搅拌下将放于一个3.8cm2塑料盆中且处于第一扩展真叶阶段的两个菜豆(Sieva lima bean)植物的叶子浸入试验溶液中3秒并在通风橱中干燥。然后将盆放入25.4cm的顶部带拉链的塑料袋中并用10只二龄幼虫侵染。在5天时观察死亡率、进食减退或任何正常换羽干扰。
在该试验中,实施例16的化合物在300ppm下与未处理对照相比显示出超过50%的死亡率。
Claims (30)
1.通式(I)的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐:
其中A为式A1或A2的基团:
以及其中
m为0、1、2、3、4或5;
n为0、1、2、3、4或5;
X为硫或氧;
R1、R2各自独立地为卤素、OH、SH、氰基、C1-C6烷基、C1-C6烷氧基、C1-C8烷硫基、C2-C6链烯氧基,其中上述基团的脂族基团中的碳原子可以带有1、2或3个选自卤素和C1-C6烷氧基的基团R#的任何组合,基团Y-Ar,其中
Y为单键、氧、硫、C1-C6亚烷基或C1-C6亚烷基氧基,
Ar为苯基或萘基,其中Ar未被取代或可以带有1、2、3、4或5个选自卤素、C1-C6烷基和C1-C6烷氧基的基团的任何组合;
以及其中与苯基环的相邻碳原子键合的两个基团R1或两个基团R2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元碳环或含有1或2个选自氧和硫的杂原子作为环成员的稠合5、6或7元杂环,且其中该稠合环未被取代或可以带有1、2、3或4个选自卤素和C1-C6烷氧基的基团R#的任何组合;
R3、R4各自独立地为氢或C1-C6烷基;
R5a、R5b、R5c、R5d各自独立地为氢、C1-C6烷基、
苯基或苄基;
R6为氢、氰基、C1-C6烷基、甲酰基、C1-C6烷基羰基、C1-C6烷氧羰基,R7为氢或C1-C6烷基。
2.如权利要求1所要求的化合物,其中R3为氢或C1-C4烷基。
3.如权利要求1所要求的化合物,其中R4为氢或C1-C4烷基。
4.如权利要求2所要求的化合物,其中R4为氢或C1-C4烷基。
5.如权利要求1-4中任一项所要求的化合物,其中R3和R4均为氢。
6.如权利要求1-4中任一项所要求的化合物,其中R3为氢且R4为C1-C4烷基。
7.如权利要求1-4中任一项所要求的化合物,其中式I中的A为基团A1,其中R6为氢、C1-C4烷基、甲酰基、C1-C6烷基羰基或C1-C6烷氧羰基。
8.如权利要求5所要求的化合物,其中式I中的A为基团A1,其中R6为氢、C1-C4烷基、甲酰基、C1-C6烷基羰基或C1-C6烷氧羰基。
9.如权利要求6所要求的化合物,其中式I中的A为基团A1,其中R6为氢、C1-C4烷基、甲酰基、C1-C6烷基羰基或C1-C6烷氧羰基。
10.如权利要求1-4中任一项所要求的化合物,其中式I中的A为基团A2,其中R7为氢。
11.如权利要求5所要求的化合物,其中式I中的A为基团A2,其中R7为氢。
12.如权利要求6所要求的化合物,其中式I中的A为基团A2,其中R7为氢。
13.如权利要求1-4中任一项所要求的化合物,其中基团R5a、R5b、R5c和R5d各自为氢。
14.如权利要求11所要求的化合物,其中基团R5a、R5b、R5c和R5d各自为氢。
15.如权利要求1-4中任一项所要求的化合物,其中基团R5a、R5b、R5c和R5d中至少一个不为氢。
16.如权利要求11所要求的化合物,其中基团R5a、R5b、R5c和R5d中至少一个不为氢。
17.如权利要求1-4中任一项所要求的化合物,其中式I中的n为0、1或2。
18.如权利要求16所要求的化合物,其中式I中的n为0、1或2。
19.如权利要求1-4中任一项所要求的化合物,其中式I中的m为0、1或2。
20.如权利要求18所要求的化合物,其中式I中的m为0、1或2。
21.如权利要求17所要求的化合物,其中n+m为整数1、2、3或4。
22.如权利要求19所要求的化合物,其中n+m为整数1、2、3或4。
23.如权利要求18或20所要求的化合物,其中n+m为整数1、2、3或4。
24.如权利要求1-4中任一项所要求的化合物,其中R1和R2各自独立地选自卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和苯基,该苯基未被取代或被1-5个卤素、1-3个C1-C6烷基或C1-C6烷氧基的任何组合取代。
25.如权利要求23所要求的化合物,其中R1和R2各自独立地选自卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和苯基,该苯基未被取代或被1-5个卤素、1-3个C1-C6烷基或C1-C6烷氧基的任何组合取代。
26.一种防治选自昆虫的动物害虫的方法,包括使所述动物害虫,其栖息地,繁殖地,食物源,动物害虫在其中生长或可能生长的植物、种子、土壤、区域、材料或环境或需要保护以免受昆虫侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种如权利要求1所定义的通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其盐接触。
27.一种保护作物免受昆虫侵袭或侵染的方法,包括使作物与杀虫有效量的至少一种如权利要求1所定义的通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其盐接触。
28.一种农业组合物,包含至少一种如权利要求1所定义的通式I的1-(唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其盐和固体或液体载体。
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