CN1175257A - 3-芳基-季酮酸衍生物、其生产和作为杀虫剂的应用 - Google Patents
3-芳基-季酮酸衍生物、其生产和作为杀虫剂的应用 Download PDFInfo
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- CN1175257A CN1175257A CN95197629A CN95197629A CN1175257A CN 1175257 A CN1175257 A CN 1175257A CN 95197629 A CN95197629 A CN 95197629A CN 95197629 A CN95197629 A CN 95197629A CN 1175257 A CN1175257 A CN 1175257A
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- 239000003096 antiparasitic agent Substances 0.000 title abstract 2
- 229940125687 antiparasitic agent Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 154
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 70
- 150000002367 halogens Chemical group 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 64
- 239000001301 oxygen Substances 0.000 claims abstract description 45
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 45
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 44
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000005864 Sulphur Substances 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 33
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims description 148
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 97
- 229910052801 chlorine Inorganic materials 0.000 claims description 97
- -1 isobutyl- Chemical group 0.000 claims description 93
- 239000011737 fluorine Substances 0.000 claims description 87
- 229910052731 fluorine Inorganic materials 0.000 claims description 87
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 83
- 239000002585 base Substances 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 48
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 48
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 239000011230 binding agent Substances 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
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- 239000000126 substance Substances 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- RHJFWPOOZFAPEB-UHFFFAOYSA-N [O].C1=CSC=N1 Chemical compound [O].C1=CSC=N1 RHJFWPOOZFAPEB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 238000003780 insertion Methods 0.000 claims description 6
- 230000037431 insertion Effects 0.000 claims description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
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- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 5
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- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910000765 intermetallic Inorganic materials 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 238000004891 communication Methods 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 51
- 239000000203 mixture Substances 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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- 239000003995 emulsifying agent Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
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- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
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- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
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- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
本发明涉及新的式(Ⅰ)新的3-芳基-4-羟基-△3-二氢呋喃酮衍生物,其中A和B与其所键合的碳原子一起形成5-或7-元环,该环中插入至少一个杂原子且是未取代或取代的;X代表烷基、卤素或烷氧基;Y代表氢、烷基、卤素、烷氧基或卤代烷基;Z代表烷基、卤素或烷氧基;n代表数字0、1、2或3;G代表氢(a)或所示的基团(b)、(c)、(d)、(e)、(f)或(g)之一;E代表相应金属离子或铵离子;L代表氧或硫;M代表氧或硫;R1、R2、R3、R4、R5、R6和R7具有说明书中所指示的含义。本发明还涉及生产所述化合物的方法和所述化合物作为杀寄生虫剂的应用,以及其中R8代表烷基的式(Ⅱ)的中间产物。
Description
本发明涉及新的3-芳基-4-羟基-Δ3-二氢-呋喃酮衍生物(3-芳基-季酮酸衍生物),其制备方法和作为农药的应用。
业已公开某些取代的Δ3-二氢呋喃-2-酮衍生物具有除草性能(参见DE-A-4014420)。用作原料化合物的季酮酸衍生物(例如3-(2-甲基-苯基)-4-羟基-5-(4-氟苯基)-Δ3-二氢呋喃-2-酮)的合成也已描述于DE-A-4014420中。相似结构的化合物可由Campbell等人发表于《化学协会杂志,Perkin学报》(J.Chem.Soc.,Perkin Trans.)1,1985,(8)1567-76)中的文章得知,该文中未提到这些化合物的杀虫和/或杀螨活性。再则,具有除草、杀螨和杀虫性能的3-芳基-Δ3-二氢呋喃酮衍生物公开于EP-528156中,但描述于该文中的作用并不总是令人满意的。
业已发现新的式(I)3-芳基-4-羟基-Δ3-二氢呋喃酮衍生物,其中A和B与其所键合的碳原子一起形成未取代或取代的5-或7-元环,该环
中插入至少一个杂原子,X 代表烷基、卤素或烷氧基,Y 代表氢、烷基、卤素、烷氧基或卤代烷基,Z 代表烷基、卤素或烷氧基,n 代表数字0、1、2或3,G 代表氢(a)或下列基团之一,E 代表相应金属离子或铵离子,L 代表氧或硫,M 代表氧或硫,R1 代表烷基、链烯基、烷氧基烷基、烷硫基烷基、多烷氧基烷基,它们
各任选由卤素取代,或代表环烷基,该环烷基可以插入至少一个杂原
子且它任选由卤素、烷基或烷氧基取代,或代表在每种情况下任选取
代的苯基、苯烷基、杂芳基、苯氧基烷基或杂芳氧基烷基,R2 代表烷基、链烯基、烷氧基烷基或多烷氧基烷基,它们各任选由卤素
取代,或代表环烷基,该环烷基任选由卤素、烷氧基或烷基取代,或
代表在每种情况下任选取代的苯基或苄基,R3、R4和R5相互独立地代表烷基、烷氧基、烷基氨基、二烷基氨基、
烷硫基、链烯基硫基或环烷基硫基,它们各任选由卤素取代,或代表
在每种情况下任选取代的苯基、苄基、苯氧基或苯硫基,且R6和R7相互独立地代表氢,或代表烷基、环烷基、链烯基、烷氧基或烷
氧基烷基,它们各任选由卤素取代,或代表在每种情况下任选取代的
苯基或苄基,或在一起代表任选由氧或硫插入的烷二基。
考虑基团G的各种含义(a)、(b)、(c)、(d)、(e)、(f)和(g),得下列主结构(Ia)至(Ig): 其中A、B、E、L、M、X、Y、Z、R1、R2、R3、R4、R5、R6、R7和n具有上述含义。
由于其一或多个手性中心,式(Ia)至(Ig)化合物通常以立体异构体混合物的形式获得。它们可以以其非对映异构体的形式使用,但也可以以其纯非对映异构体或对映体的形式使用。
再则,业已发现,新的式(I)3-芳基季酮酸衍生物通过描述于下文的方法之一获得:(A)式(Ia)的3-芳基-季酮酸,其中A、B、X、Y、Z和n具有上述的含义,如下获得:使式(II)的羧酸酯其中A、B、X、Y、Z和n具有上述含义,且R8 代表烷基、优选C1-C8-烷基,在稀释剂存在下和在碱存在下,进行分子内缩合反应;和(B)式(Ib)化合物,其中A、B、X、Y、Z、R1和n具有上述含义,如下获得:使式(Ia)化合物,A、B、X、Y、Z和n具有上述含义,α)如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(III)酰基卤反应,其中R1具有上述含义,且Hal 代表卤素,特别是氯和溴;或β)如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(IV)的羧酸酐反应,
R1-CO-O-CO-R1 (IV)其中R1 具有上述含义;和(C)式(Ic-1)化合物,其中A、B、X、Y、Z、R2和n具有上述含义,且M 代表氧或硫,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(V)的氯甲酸酯或氯甲酸硫酯反应,
R2-M-CO-Cl (V)其中R2和M具有上述含义;和(D)式(Ic-2)化合物其中A、B、R2、X、Y、Z和n具有上述含义,且M代表氧或硫,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,α)如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(VI)氯单硫代甲酸酯或氯二硫代甲酸酯反应,其中M和R2具有上述含义;或β)如果需要在稀释剂存在下和如果需要碱存在下,与二硫化碳,且之后与式(VII)的烷基卤反应,
R2-Hal (VII)其中R2 具有上述含义,且Hal 代表氯、溴或碘;和(E)式(Id)化合物,其中A、B、X、Y、Z、R3和n具有上述含义,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(VIII)的磺酰氯反应,
R3-SO2-Cl (VIII)其中R3具有上述含义;和(F)式(Ie)化合物其中A、B、L、X、Y、Z、R4、R5和n具有上述含义,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(IX)的磷化合物反应,其中L、R4和R5具有上述含义,和Hal 代表卤素,特别是氯或溴;(G)式(If)化合物,其中A、B、X、Y、Z和n具有上述含义,且E 代表相应金属离子或铵离子,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下,与式(X)或(XI)的金属化合物或胺反应,其中Me 代表一或二价金属,例如碱金属或碱土金属离子,例如Li+、Na+、
K+、Ca2+或Mg2+,t 代表数字1或2,R10、R11和R12相互独立地代表氢或烷基(特别是C1-C8-烷基)和R13 代表氢、羟基或C1-C4-烷氧基;和(H)另外,业已发现,式(Ig)化合物,其中A、B、L、X、Y、Z、R6、R7和n具有上述含义,如下获得:使式(Ia)化合物,A、B、X、Y、Z和n具有上述含义,α)如果需要在稀释剂存在下和如果需要在催化剂存在下,与式(XII)化合物反应,
再则,已经发现,新的式(I)化合物的突出之处在于其显著的杀虫和杀螨作用。在上下文中提到的结构式中列出的优选取代基或基团的范围在下文中说明。A和B优选代表C4-C6-烷二基,该烷二基任选由相同或不同的下列取代基
单或多取代:卤素、C1-C8-烷基、C3-C8-环烷基、C1-C8-卤代烷
基、C1-C6-烷氧基、C1-C6-烷硫基或苯基,且该烷二基中的不直接
代基单至四取代:氟、氯、C1-C6-烷基、C3-C6-环烷基、C1-C6-
卤代烷基、C1-C4-烷氧基、C1-C4-烷硫基或苯基,且该烷二基中的
不直接相邻的一或二个碳原子由基团或由氧或由硫替代。A和B非常特别优选代表C4-C5-烷二基,该烷二基任选由相同或不同的下
列取代基单至三取代:氟、氯、甲基、乙基、正丙基、异丙基、正丁
基、异丁基、仲丁基、叔丁基、环己基、三氟甲基、甲氧基、甲硫基
或苯基,且该烷二基中的一个碳原子由下式基团或由氧或由硫替代。X 优选代表C1-C6-烷基、卤素或C1-C6-烷氧基。X 特别优选代表C1-C4-烷基、氟、氯、溴或C1-C4-烷氧基。X 非常特别优选代表甲基、乙基、正丙基、异丙基、氟、氯、溴、甲氧基或乙氧基。Y 优选代表氢、C1-C6-烷基、卤素、C1-C6-烷氧基或C1-C3-卤代烷基。Y 特别优选代表氢、C1-C4-烷基、氟、氯、溴、C1-C4-烷氧基或C1-C2卤代烷基。Y 非常特别优选代表氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、氟、氯、溴、甲氧基、乙氧基或三氟甲基。Z 优选代表C1-C6-烷基、卤素或C1-C6-烷氧基。Z 特别优选代表C1-C4-烷基、氟、氯、溴或C1-C4-烷氧基。Z 非常特别优选代表甲基、乙基、丙基、异丙基、正丁基、异丁基、叔丁基、氟、氯、溴、甲氧基或乙氧基。G 优选代表氢(a)或下列基团之一:其中E 代表相应金属离子或铵离子,L 代表氧或硫,且M 代表氧或硫,R1 优选代表C1-C20-烷基、C2-C20-链烯基、C1-C8-烷氧基-C1-C8-烷
基、C1-C8-烷硫基-C1-C8-烷基或多-C1-C8-烷氧基-C2-C8-烷基,它
们各任选由卤素单或多取代,或代表任选由卤素、C1-C6-烷基或
C1-C6-烷氧基取代的C3-C8-环烷基且其中之不直接相邻的一或二个
亚甲基任选由氧和/或硫替代,或代表苯基,该苯基任选由下列基团
单至五取代:卤素、硝基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-
卤代烷基、C1-C6-卤代烷氧基、C1-C6-烷硫基或C1-C6-烷基磺酰
基,或代表苯基-C1-C6-烷基,该基团任选由下列基团单至五取代:
卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基或C1-C6-卤
代烷氧基,
或代表吡啶基、噻吩基、呋喃基、吡唑基、嘧啶基或噻唑基,它们各
任选由卤素或C1-C6-烷基单或二取代,
或代表苯氧基-C1-C6-烷基,该基团任选由卤素或C1-C6-烷基单至三
取代,
或代表吡啶氧基-C1-C6-烷基、嘧啶氧基-C1-C6-烷基或噻唑氧基-
C1-C6-烷基,它们各优选由卤素、氨基或C1-C6-烷基单或二取代,R2 优选代表C1-C20-烷基、C2-C20-链烯基、C1-C8-烷氧基-C2-C8-烷
基或多-C1-C8-烷氧基-C2-C8-烷基,它们各任选由卤素单或多取
代,
或代表C3-C8-环烷基,该环烷基任选由卤素、C1-C4-烷基或C1-C4-
烷氧基单或多取代,
或代表苯基或苄基,它们各任选由下列基团单至三取代:卤素、硝基、
C1-C6-烷基、C1-C6-烷氧基或C1-C6-卤代烷基,R3 优选代表任选由卤素单或多取代的C1-C8-烷基,或代表苯基或苄
基,它们各任选下列基团单或多取代:卤素、C1-C6-烷基、C1-C6-
烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基,R4和R5相互独立地优选代表C1-C8-烷基、C1-C8-烷氧基、C1-C8-烷基
氨基、二-(C1-C8-)-烷基氨基、C1-C8-烷硫基、C3-C6-链烯基硫基
或C3-C7-环烷基硫基,它们各任选由卤素单或多取代,
或代表苯基、苯氧基或苯硫基,它们各任选由下列基团单或多取代:
卤素、硝基、氰基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-
烷硫基、C1-C4-卤代烷硫基、C1-C4-烷基或C1-C4-卤代烷基,R6和R7相互独立地优选代表氢,或代表C1-C8-烷基、C3-C8-环烷基、
C1-C8-烷氧基、C3-C8-链烯基或C1-C8-烷氧基-C1-C8-烷基,它们
各任选由卤素单或多取代,
或代表苯基或苄基,它们各任选由下列基团单至三取代:卤素、
C1-C8-烷基、C1-C8-卤代烷基或C1-C8-烷氧基,或在一起代表C2-
C6-烷二基,该烷二基任选由氧或硫插入,R9 优选代表氢、Q、COQ或CO2Q,
其中Q 可以是上述业已提到的R2中优选的含义,n 优选代表0、1或2。G 特别优选代表氢(a)或下列基团之一:其中E 代表相应金属离子或铵离子,L 代表氧或硫,且M 代表氧或硫,R1 特别优选代表C1-C16-烷基、C2-C16-链烯基、C1-C6-烷氧基-C1-
C6-烷基、C1-C6-烷硫基-C1-C6-烷基或多-C1-C6-烷氧基-C1-C6-烷
基,它们各任选由氟、氯单至六取代,
或代表C3-C7-环烷基,该环烷基任选由氟、氯、C1-C5-烷基或C1-
C5-烷氧基取代,且该环烷基中之不直接相邻的一或二个亚甲基任选
由氧和/或硫替代,
或代表苯基,该苯基任选由下列基团单至三取代:氟、氯、溴、硝基、
C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代烷基、C1-C3-卤代烷氧
基、C1-C4-烷硫基或C1-C4-烷基磺酰基,
或代表苯基-C1-C4-烷基,该基团任选由下列基团单至三取代:氟、
氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代烷基或C1-C3-
卤代烷氧基,
或代表吡啶基、噻吩基、呋喃基、吡唑基、嘧啶基或噻唑基,它们各
任选由氟、氯、溴或C1-C4-烷基单或二取代,
或代表苯氧基-C1-C5-烷基,该基团任选由氟、氯、溴或C1-C4-烷基
单或二取代,
或代表嘧啶氧基-C1-C5-烷基、吡啶氧基-C1-C5-烷基或噻唑氧基-
C1-C5-烷基,它们各优选由氟、氯、溴、氨基或C1-C4-烷基单或二
取代,R2 特别优选代表C1-C16-烷基、C2-C16-链烯基、C1-C6-烷氧基-C2-
C6-烷基或多-C1-C6-烷氧基-C2-C6-烷基,它们各任选由氟或氯单至
六取代,
或代表C3-C7-环烷基,该环烷基任选由氟、氯、C1-C3-烷基或C1-
C3-烷氧基单至六取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、氯、溴、
硝基、C1-C4-烷基、C1-C3-烷氧基或C1-C3-卤代烷基,R3 特别优选代表任选由氟或氯单至六取代的C1-C6-烷基,或代表苯基
或苄基,它们各任选下列基团单或二取代:氟、氯、溴、C1-C5-烷
基、C1-C5-烷氧基、C1-C3-卤代烷基、C1-C3-卤代烷氧基、氰基或
硝基,R4和R5相互独立地特别优选代表C1-C6-烷基、C1-C6-烷氧基、C1-C6-
烷基氨基、二-(C1-C6-)-烷基氨基、C1-C6-烷硫基、C3-C4-链烯基
硫基或C3-C6-环烷基硫基,它们各任选由氟或氯单至六取代,
或代表苯基、苯氧基或苯硫基,它们各任选由下列基团单或二取代:
氟、氯、溴、硝基、氰基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-
烷硫基、C1-C3-卤代烷硫基、C1-C3-烷基或C1-C3-卤代烷基,R6和R7相互独立地特别优选代表氢,或代表C1-C6-烷基、C3-C6-环烷
基、C1-C6-烷氧基、C3-C6-链烯基或C1-C6-烷氧基-C1-C6-烷基,
它们各任选由氟或氯单至六取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、氯、溴、
C1-C5-烷基、C1-C5-卤代烷基或C1-C5-烷氧基,或在一起代表C2-
C6-烷二基,该烷二基任选由氧或硫插入,R9 特别优选代表氢、Q、COQ或CO2Q,
其中Q 代表C1-C6-烷基、苯基或苄基,n 特别优选代表0或1。G 非常特别优选代表氢(a)或下列基团之一:其中E 代表相应金属离子或铵离子,L 代表氧或硫,且M 代表氧或硫,R1 非常特别优选代表C1-C14-烷基、C2-C14-链烯基、C1-C4-烷氧基-
C1-C6-烷基、C1-C4-烷硫基-C1-C6-烷基或多-C1-C4-烷氧基-C1-
C4-烷基,它们各任选由氟或氯单至三取代,
或代表C3-C6-环烷基,该环烷基任选由下列基团取代:氟、氯、甲
基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、甲氧基、乙氧基、
丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基或叔丁氧基,且该
环烷基中的一个亚甲基任选由氧或硫替代,
或代表苯基,该苯基任选由下列基团单或二取代:氟、氯、溴、甲基、
乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基、甲
硫基、乙硫基、甲磺酰基、乙磺酰基或硝基,
或代表苯基-C1-C3-烷基,该基团任选由下列基团单或二取代:氟、
氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基、
三氟甲氧基,
或代表噻吩基、呋喃基或吡啶基,它们各任选由氟、氯、溴、甲基或
乙基单或二取代,
或代表苯氧基-C1-C4-烷基,该基团任选由氟、氯、甲基或乙基单或
二取代,
或代表吡啶氧基-C1-C4-烷基、嘧啶氧基-C1-C4-烷基或噻唑氧基-
C1-C4-烷基,它们各任选由氟、氯、氨基、甲基或乙基单或二取代,R2 非常特别优选代表C1-C14-烷基、C2-C14-链烯基、C1-C4-烷氧基-
C2-C6-烷基或多-C1-C4-烷氧基-C2-C6-烷基,它们各任选由氟或氯
单至三取代,
或代表C3-C6-环烷基,该环烷基任选由氟、氯、甲基、乙基、丙基、
异丙基或甲氧基单至三取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、氯、硝
基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基或三氟甲基,R3 非常特别优选代表任选由氟或氯单至三取代的甲基、乙基、丙基或异
丙基,或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、
氯、溴、甲基、乙基、丙基、异丙基、叔丁基、甲氧基、乙氧基、异
丙氧基、叔丁氧基、三氟甲基、三氟甲氧基、氰基或硝基,R4和R5相互独立地非常特别优选代表C1-C4-烷基、C1-C4-烷氧基、
C1-C4-烷基氨基、二-(C1-C4-)-烷基氨基或C1-C4-烷硫基,它们各
任选由氟或氯单至三取代,
或代表苯基、苯氧基或苯硫基,它们各任选由下列基团单或二取代:
氟、氯、溴、硝基、氰基、C1-C2-烷氧基、C1-C2-氟代烷氧基、C1-C2-
烷硫基、C1-C2-氟代烷硫基、C1-C2-烷基或C1-C2-氟代烷基,R6和R7相互独立地非常特别优选代表氢,或代表C1-C4-烷基、C3-C6-
环烷基、C1-C4-烷氧基、C3-C4-链烯基或C1-C4-烷氧基-C1-C4-烷
基,它们各任选由氟或氯单至三取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、氯、溴、
C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基,或在一起代表C2-
C6-烷二基,该烷二基任选由氧或硫插入,R9 非常特别优选代表氢、Q、COQ或CO2Q,
其中Q 代表C1-C4-烷基、苯基或苄基,n 非常特别优选代表0或1。
在给出的定义中,饱和或未饱和烃基,以及与杂原子相连的烃基,例如烷氧基或烷硫基,在可能情况下可以是直链或支链的。
任选多取代的基团可以由相同或不同取代基取代,所述的取代基是这些基团所提到的取代基。
基团或说明的上述定义,一般或优选的范围,可以按需要任意组合,即各自范围和优选范围间的组合也是可以的。它们适用于终产物、相应地适用于前体和中间体。
本发明所优选的是那些其中存在上述所提到的优选含义组合的式(I)化合物。
本发明所特别优选的是那些其中存在上述所提到的特别优选含义组合的式(I)化合物。
本发明所非常特别优选的是那些其中存在上述所提到的非常特别优选含义组合的式(I)化合物。
优选组的化合物是那些其中n代表数字1和取代基Z是在苯基6-位上的式(I)化合物。
再一组优选组的化合物是那些其中n代表数字0和Y同时不代表氢的式(I)化合物。
另一组优选化合物是那些其中n代表数字1和y同时代表氢的式(I)化合物。
除了在制备实施例中提到的化合物外,可以单独提到列于表1至表4中的式(Ia)化合物。
表1
表2 含下式的化合物其中X、Y和Z具有表1中给出的含义。表3 含有下式的化合物其中X、Y和Z具有表1中给出的含义。表4 含有下式化合物其中X、Y和Z是有表1中给出的含义。
X | Y | Z |
CH3 | CH3 | H |
Cl | Cl | H |
CH3 | Cl | H |
Cl | CH3 | H |
CH3 | OCH3 | H |
OCH3 | CH3 | H |
Cl | OCH3 | H |
OCH3 | Cl | H |
OCH3 | OCH3 | H |
Cl | H | Cl |
Cl | H | F |
Cl | H | OCH3 |
CH3 | H | CH3 |
CH3 | H | OCH3 |
CH3 | H | Cl |
OCH3 | H | OCH3 |
CH3 | CH3 | CH3 |
CH3 | CH3 | OCH3 |
CH3 | OCH3 | CH3 |
Cl | Cl | Cl |
Cl | CF3 | Cl |
如果根据方法(C),采用3-(2,4,6-三甲基苯基)-5,5-亚乙基氧杂亚甲基-季酮酸和氯甲酸乙氧基乙酯为原料,根据本发明的反应途径可以由下列反应式代表:
如果根据方法(Dα),采用3-(2,4,6-三甲基苯基)-5,5-亚乙基氧杂亚乙基-季酮酸和氯单硫代甲酸甲酯为原料,根据本发明的反应途径可以由下列反应式代表:
如果根据方法(Dβ),采用3-(2,4,6-三甲基苯基)-5,5-亚乙基硫杂亚乙基-季酮酸、二硫化碳和甲基碘为原料,根据本发明的反应途径可以由下列反应式代表:
如果根据方法(F),采用3-(2,4-二甲基苯基)-5,5-亚乙基硫杂亚乙基-季酮酸和氯甲硫代磷酸-(2,2,2-三氟乙基酯)为原料,根据本发明的反应途径可以由下列反应式代表:
如果根据方法(Hα),采用3-(2,4,6-三甲基苯基)-5,5-亚乙基氧杂亚乙基-季酮酸和异氰酸乙酯为原料,根据本发明的反应途径可以由下列反应式代表:
如果根据方法(Hβ),采用3-(2,4,6-三甲基苯基)-5,5-(亚乙基乙酰氨基-亚乙基)-季酮酸和二甲基氨基甲酰氯为原料,根据本发明的反应途径可以由下列反应式代表:式(II)化合物其中A、B、X、Y、Z、n和R8具有上述含义,它在上面的方法(A)中需要作为原料,该化合物是新的。
式(II)化合物可以如下获得;例如,将式(XIV)的2-羟基羧酸衍生物,其中R8′代表氢(XIVa)或烷基(优选C1-C8-烷基)(XIVb)和A和B具有上述含义,用式(XV)的苯基乙酰卤酰化,其中X、Y、Z和n具有上述含义,和Hal 代表氯或溴,(《化学通讯》(Chem.Reviews)52,237-416(1953));且在R8’=氢的情况下,将所形成的式(IIa)化合物其中A、B、X、Y、Z和n具有上述含义,如果需要进行酯化(《化学工业)》(Chem.Ind.)(伦敦)1568(1968))。
某些式(XIV)化合物是已知的和/或可以通过已知的方法制备,例如由式(XVI)的氰基醇其中A和B具有上述含义,[参见,例如,Nasarow,Unkowskii,Zh.Obshch.Khim.26,3486(1956)或Bennett,Waddington,《化学协会杂志)》(J.Chem.Soc.)2831(1929)]。
某些式(XVI)的化合物是已知的和/或可以通过已知的方法制备(参见Eichen,Fritz;Schmidt,Michal;Buchborn,Helga;Arch.Pharm.320,348-61,1987;Sargsyan,M.S.;Ukrtumyan,S.A.;GevorkyanA.A.;Arm.Khim.Zh 38 494-8,1985)。
式(XV)的苯基乙酰氯是已知的和/或可以通过已知的方法制备(参见,例如,Lutz,Hinkley,《美国化学协会杂志》(J.Amer.Chem.Soc.)72,4091(1950),Harispe,Ann.Chim.(巴黎)11,6,第249、282、283页(1936))。
式(III)的酰基卤、式(IV)的羧酸酐、式(V)的氯甲酸酯或氯甲酸硫代酯、式(VI)的氯单硫代甲酸酯或氯二硫代甲酸酯、式(VII)的烷基卤、式(VIII)的磺酰氯、式(IX)的磷化合物和式(X)和(XI)的金属化合物或胺和式(XII)的异氰酸酯或式(XIII)的氨基甲酰氯,这些化合物是进行方法(B)、(C)、(D)、(E)、(F)、(G)和(H)需要的另外的原料,它们一般是已知有机或无机化学的化合物。
方法(A)的特征在于,使式(II)的化合物,其中A、B、X、Y、Z、n和R8具有上述含义,在碱存在下进行分子内缩合反应。
可以在方法(A)中采用的稀释剂是所有的惰性有机溶剂。可以优选下列溶剂:烃类,如甲苯和二甲苯,还有醚类,如二丁基醚、四氢呋喃、二噁烷、乙二醇二甲醚和二甘醇二甲醚,还有极性溶剂,如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基-吡咯烷酮,以及醇类,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
进行本发明方法(A)时可以采用的碱(脱质子剂)是所有的常规质子受体。可以优选采用下列:碱金属或碱土金属的氧化物、氢氧化物或碳酸盐,如氢氧化钠、氢氧化钾、氧化镁、氧化钙、碳酸钠、碳酸钾和碳酸钙,所有这些也可以在相转移催化剂存在下进行,催化剂如氯化三乙基苄基铵、溴化四丁基铵、Adogen 464(氯化甲基三烷基(C8-C10)铵)或TDA1(三-(甲氧基乙氧基-乙基)-胺)。
还可以使用碱金属,如钠或钾。可以采用的其它物质是碱金属或碱土金属的氨化物和氢化物,如氨基钠、氢化钠和氢化钙,以及也可以是碱金属醇化物,如甲醇钠、乙醇钠和叔丁醇钾。
当进行本发明方法(A)时,反应温度可以在相当宽的范围内变化。通常,该方法是在-30℃和250℃间的温度下进行,优选在0℃和150℃之间进行。
本发明方法(A)通常是在常压下进行的。
当进行方法(A)时,式(II)的反应物和脱质子碱通常是以摩尔量进行的。然而,过量使用一或另一种组分(至多3摩尔)也是可能的。
方法(Bα)的特征在于,使式(Ia)的化合物与式(III)的羧酸卤反应。
可以在本发明方法(Bα)中采用的稀释剂是所有的对酰基卤有足够惰性的溶剂。可以优选采用下列溶剂:烃类,如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃类,如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,另外还有酮类,如丙酮和甲基异丙基酮,而且还有醚类,如二乙醚、四氢呋喃和二噁烷,且也可以是羧酸酯类,如乙酸乙酯,或其它强极性溶剂,如二甲亚砜和环丁砜。如果酰基卤对水解足够的稳定,则反应也可以在水存在下进行。
适合于本发明方法(Bα)反应的酸结合剂是所有的常规酸受体。可以优选采用下列:季胺类,如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBU)、二氮杂二环十一碳烯(DBN)、Hunig碱和N,N-二甲基苯胺,还有碱土金属氧化物,如氧化镁和氧化钙,另外还有碱金属碳酸盐和碱土金属的碳酸盐,如碳酸钠、碳酸钾和碳酸钙,和碱金属氢氧化物,如氢氧化钠和氢氧化钾。
当进行本发明方法(Bα)时,反应温度可以在相当宽的范围内变化。通常,该方法是在-20℃和150℃间的温度下进行,优选在0℃和100℃之间进行。
当进行方法(Bα)时,式(Ia)的原料和式(III)的羧酸卤通常是以大致等量进行的。然而,过量采用羧酸卤(至多5摩尔)也是可能的。收集是通过常规方法进行的。
方法(Bβ)的特征在于,使式(Ia)化合物与式(IV)的羧酸酐反应。
优选用于本发明方法(Bβ)的稀释剂是那些采用酰基氯时也优选考虑的稀释剂。此外,过量的羧酸酐也可以作为稀释剂。
当进行本发明方法(Bβ)时,反应温度可以在相当宽的范围内变化。通常,该方法是在-20℃和150℃间的温度下进行,优选在0℃和100℃之间进行。
当进行方法(Bβ)时,式(Ia)原料和式(IV)的羧酸酐通常是以大致等量进行的。然而,过量采用羧酸酐(至多5摩尔)也是可能的。收集是通过常规方法进行的。
通常,在该程序中将稀释剂和过量的羧酸酐以及所形成的羧酸通过蒸馏或通过用有机溶剂或用水洗涤而除去。
方法(C)的特征在于,使式(Ia)的化合物与式(V)的氯甲酸酯或氯甲酸硫代酯反应。
适合于本发明方法(C)反应的酸结合剂是所有的常规酸受体。可以优选采用下列:季胺类,如三乙胺、吡啶、DABCO、DBU、DBN、Hunig碱和N,N-二甲基苯胺,还有碱土金属氧化物,如氧化镁和氧化钙,另外还有碱金属碳酸盐和碱土金属的碳酸盐,如碳酸钠、碳酸钾和碳酸钙,和碱金属氢氧化物,如氢氧化钠和氢氧化钾。
可以在本发明方法(C)中采用的稀释剂是所有的对式(V)的化合物有足够惰性的溶剂。可以优选采用下列溶剂:烃类,如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃类,如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,另外还有酮类,如丙酮和甲基异丙基酮,而且还有醚类,如二乙醚、四氢呋喃和二噁烷,且也可以是羧酸酯类,如乙酸乙酯,或其它强极性溶剂,如二甲亚砜和环丁砜。
当进行本发明方法(C)时,反应温度可以在相当宽的范围内变化。如果该方法是在稀释剂和酸结合剂存在下进行的,该反应温度通常是在-20℃和100℃间的温度下进行,优选在0℃和50℃之间进行。
本发明方法(C)通常是在常压下进行的。
当进行方法(C)时,式(Ia)原料和式(V)的氯甲酸酯或氯甲酸硫代酯通常是以大致等量进行的。然而,采用一种或另一种组分过量(至多2摩尔)也是可能的。收集是通过常规方法进行的。通常,在该程序中,将沉淀出的盐移出,且所剩的反应混合物通过汽提出稀释剂来浓缩。
在制备方法(Dα)中,每摩尔式(Ia)的原料化合物在0至120℃下,优选在20至60℃下,与通常大致1摩尔的式(VI)氯单硫代甲酸酯或氯二硫代甲酸酯反应。
任选加入的适合的稀释剂是所有的惰性极性有机溶剂,如醚类、羧酸酯类、卤代烃类、酰胺类、醇类、砜类和亚砜类。
优选采用的物质是二甲亚砜、二氯甲烷、乙酸乙酯、四氢呋喃、二甲基甲酰胺或二甲硫。
如果在优选的实施方案中,式(Ia)化合物的烯醇盐通过加入强的脱质子剂制备,例如加入氢化钠或叔丁醇钾,可以省去加入另外的酸结合剂。
如果采用酸结合剂,则常规的无机或有机碱是适合的,可以提到的实例是氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
该反应可以在常压下或在加压下进行,优选在常压下进行。收集是通过常规方法进行的。
在制备方法(Dβ)时,每摩尔式(Ia)的原料化合物加入等摩尔或过量的二硫化碳。此方法优选在温度0至50℃下进行,特别是在20至30℃下进行。
可以用于方法(D3)中的碱是所有的常规质子受体。可以优选采用的物质是碱金属氢化物、碱金属醇化物、碱金属碳酸盐、碱金属碳酸氢盐、碱土金属碳酸盐、碱土金属碳酸氢盐或含氮的碱。可以提到的实例是氢化钠、甲醇钠、氢氧化钠、氢氧化钙、碳酸钾、碳酸氢钠、三乙胺、二苄基胺、二异丙基胺、吡啶、喹啉、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)和二氮杂二环十一碳烯(DBU)。
可以用在此方法中的稀释剂是所有的常规溶剂。
可以优选采用下列:芳族烃类,如苯或甲苯,醇类,如甲醇、乙醇、异丙醇或乙二醇,腈类,如乙腈,醚类,如四氢呋喃或二噁烷,酰胺类,如二甲基甲酰胺,或其它极性溶剂,如二甲亚砜或环丁砜。
在大多数情况下,首先由式(Ia)化合物通过加入脱质子剂(如叔丁醇钾或氢化钠)制备相应的盐是方便的。式(Ia)与二硫化碳反应,直至中间体化合物形成完毕,例如在室温下搅拌几小时。
与式(VII)烷基卤的进一步的反应优选是在0至70℃下进行的,特别是在20至50℃下进行。为此目的,至少采用等摩尔量的烷基卤。
该方法是在常压下或在加压下进行的,优选是在常压下进行。
收集仍是通过常规方法进行的。
在制备方法(E)中,每摩尔式(Ia)的原料化合物在0至150℃,优选20至70℃下,与大致1摩尔的磺酰氯(VIII)反应。
任选加入的适合的稀释剂是所有的惰性极性有机溶剂,如醚类、羧酸类、酰胺类、腈类、砜类、亚砜类或卤代烃类,如二氯甲烷。
优选采用的物质是二甲亚砜、乙酸乙酯、四氢呋喃、二甲基甲酰胺、二甲硫或二氯甲烷。
如果在优选的实施方案中,式(Ia)化合物的烯醇盐是通过加入强的脱质子剂(如氢化钠或叔丁醇钾)来合成的,可以省去加入另外的酸结合剂。
如果采用酸结合剂,则常规无机或有机碱是适合的,可以提到的实例是氢氧化钠、碳酸钠、碳酸钾、三乙胺和吡啶。
此方法可以在常压或加压下进行,优选在常压下进行。收集是通过常规方法进行的。
在制备方法(F)中,每摩尔式(Ia)的原料化合物在-40至150℃,优选-10至110℃下,与1至2摩尔,优选1至1.3摩尔式(IX)磷化合物反应,获得结构(Ie)的化合物。
任选加入的适合的稀释剂是所有的惰性极性有机溶剂,如醚类、羧酸类、卤代烃类、酰胺类、腈类、硫化物、砜类、亚砜类等。
优选乙腈、乙酸乙酯、二氯甲烷、二甲亚砜、四氢呋喃、二甲基甲酰胺或二甲硫。
任选加入的适合的酸结合剂是常规无机或有机碱,如氢氧化物或碳酸盐。可以提到的实例是氢氧化钠、碳酸钠、碳酸钾和吡啶。
可以在常压下或在加压下进行反应,优选在常压下进行。收集是通过常规的有机化学方法进行的。所获得的终产物优选通过结晶、色谱或通过所谓“早期蒸馏”(即在真空中去除挥发组分)来纯化。
方法(G)的特征在于,使式(Ia)化合物与式(X)金属化合物或式(XI)的胺反应。
可以用于本发明方法(G)的稀释剂优选是醚类,如四氢呋喃或二噁烷、二乙醚,或是醇类,如甲醇、乙醇或异丙醇,但也可以是水。本发明方法(G)通常是在常压下进行的。该反应的温度通常是在-20℃和100℃之间,优选在0℃和50℃间。
在制备方法(Hα)中,每摩尔式(Ia)的原料化合物是在0至100℃,优选在20至50℃下,与大致1摩尔的式(XII)异氰酸酯反应。
任选加入的适合的稀释剂是所有的惰性有机溶剂,如醚类、芳烃类、羧酸酯类、卤代烃类、酰胺类、腈类、砜类或亚砜类。
如果需要,可以加入催化剂以加速反应。可以采用的催化剂非常有利的是锡有机化合物,如二月桂酸二丁基锡。此方法优选是在常压下进行。
在制备方法(Hβ)中,每摩尔式(Ia)的原料化合物是在0至150℃,优选在20至70℃下,与大致1摩尔的式(XIII)氨基甲酰氯反应。
任选加入的适合的稀释剂是所有的惰性有机溶剂,如醚类、芳烃类、羧酸酯类、卤代烃类、酰胺类、腈类、砜类或亚砜类。
优选采用的物质是二甲亚砜、乙酸乙酯、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果在优选的实施方案中,式(Ia)化合物的烯醇盐是通过加入强的脱质子剂(如氢化钠或叔丁醇钾)来合成的,可以省去加入另外的酸结合剂。
如果采用酸结合剂,则常规无机或有机碱是适合的,可以提到的实例是氢氧化钠、碳酸钠、碳酸钾、三乙胺和吡啶。
本发明活性化合物适合防治动物害虫,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面上的昆虫、蜱螨。它们优选用作植物保护剂。它们对正常的敏感和抗性种类和对所有或某些生长发育阶段有活性。上述害虫包括:等足纲,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidium vulgare)和斑鼠妇(Porcellio scaber)。倍足纲,例如,Blaniulus guttulatus。唇足纲,例如,地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigeraspec)。综合纲,例如,洁幺蚰(Scutigerella immaculata)。缨尾目,例如,西洋衣鱼(Lepisma saccharina)。弹尾目,例如,棘跳虫(Onychiurus armatus)。直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattellagermanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpaspp.)、亚洲飞蝗(Locusta migratoria)、殊种蚱蜢(Melanoplusdifferentialis)和沙漠蝗(Schistocerca gregaria)。革翅目,例如,欧洲球螋(Forficula auricularia)。等翅目,例如,犀白蚁属(Reticulitermes spp.)。虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。食毛目,例如,啮毛虱属(Trichodectes spp.)和Damalinea spp.。缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimexlectularius)、红腹猎蝽(Phodnius prolixus)和锥蝽属(Triatomaspp.)。同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisiatabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphisgossypii)、甘蓝蚜(Brevicoryne brassicae)、茶隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Doralispomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterusarundinis)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzusspp.)、忽布疣蚜(Phorodon humili)、禾谷缢管蚜(Rhopalosiphumpadi)、微叶蝉属(Empoasca spp.)、Euscelis bilobatus、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvata lugens)、红园蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotus hederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupaluspiniarius)、冬尺蛾(Cheimatobia brumata)、Lithocolletisblancardella、苹果巢蛾(Hyponomeuta padella)、小菜蛾(Plutellamaculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctischrvsorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrixthurberiella)、桔潜叶蛾(Phyllocnistis citrella)、Agrotisspp.、Euxoa spp.、Feltia spp.、棉斑实蛾(Earias insulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾((Spodoptera exigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolis flammea)、斜纹夜蛾(Prodenia litura)、粘虫属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pierisspp.)、禾草螟属(Chilo spp.)、Pyrausta nubilalis、Ephestiakuehniella、蜡螟(Galleria mellonella)、幕衣蛾(Tineolabisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophilapseudospretella)、Cacoecia podana、Capua reticulana、枞色卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homona magnanima)和栎绿卷蛾(Tortrix viridana)。鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupesbajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶甲(Phaedon cochleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachna varivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilus surinamensis)、花象甲属(Anthonomus spp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopolites sordidus)、甘蓝荚象甲(Ceuthorrhynchusassimilis)、苜蓿叶象虫(Hypera postica)、皮蠹属(Dermestesspp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptushololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、Agriotes spp.、Conoderusspp.、鳃角金龟(Melolontha melolontha)、六月金龟(Amphimallonsostitialis)和Costelytra zealandica。膜翅目,例如,锯节叶蜂属Diprion spp.、Hoplocampa spp.、田蚁属(Lasius spp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespaspp.)。双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophoraerythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyiaspp.)、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hippobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrusspp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanus spp.)、Tanniaspp.、Bibio hortulanus、瑞典麦杆蝇(Oscinella frit)、Phorbiaspp.、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitiscapitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。蚤目,例如,印鼠客蚤(Xenopsylla cheopis)和毛列蚤属(Ceratophyllus spp.)。蛛形纲,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectusmactans)。蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、茶藨瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodesspp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychus spp.)。
本发明活性化合物的突出之处在于其强的杀虫和杀螨活性。它们对土壤害虫也有活性。
它们可以特别成功地采用来防治对植物有害的昆虫,例如对辣根猿叶甲(Phaedon cochleariae)幼虫、对黑尾叶蝉(Nephotettixcincticeps)幼虫或防治对植物有害的螨类,如二点叶螨(Tetranychusurticae)。
式(I)活性化合物也具有一定的除草作用。
活性化合物可以转化成常规剂型,如溶液、乳剂、喷模粉、悬浮剂、可湿性粉剂、粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然和合成物质和在用聚合物制成的微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂,即液体溶剂和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份、矿物和植物油,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的粘合剂可以是矿物油和植物油。
也可能使用染料,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
本发明活性化合物可以其商业上可行的制剂和由这些制剂制备的使用形式存在,所述的制剂为与如下的其它活性化合物的混合物:杀虫剂、引诱剂、不育剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯、羧酸酯类、氯代烃类、苯基脲类、由微生物生产的物质,及其它。
在混合物中特别有利的组分是例如下列:杀真菌剂:
2-氨基丁烷、2-苯胺基-4-甲基-6-环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基-苯氧基)嘧啶-4-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵、苯菌灵、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、一甲呋萎灵、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异φ唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、铜制剂如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物、双代混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、氧化萎锈灵、perfurazoat、戊菌唑、戊菌隆、稻病磷、匹马菌素、哌啶宁、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、有效霉素A.Vinclozolin、代森锌、福美锌。杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC303630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、齐墩螨素(avermectin)、AZ60541、azadirachtin、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA157419、CGA184699、除线威、chlorethoxyfos、毒虫畏、定虫隆、氯甲硫磷、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、锐劲特(fipronil)、氟啶胺、fluazuron、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、咪蚜胺、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC184、NI25、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、pyrachlophos、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH5992、水杨硫磷、硫线磷、silafluofen、治螟磷、甲丙硫磷、tebufenozide、tebufenpyrad、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、YI5301/5302、zetamethrin。除草剂:
例如酰苯胺类如吡氟草胺、敌稗;芳基羧酸类如二氯吡啶甲酸、麦草畏和毒草定;芳氧羧酸类如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、氟草烟、2甲4氯、2甲4氯丙酸和绿草定;芳氧基苯氧羧酸酯类如禾草灵、噁唑禾草灵、吡氟禾草灵和喹禾灵;连氮酮类如杀草敏、哒草伏;氨基甲酸酯类如氯苯胺灵、甜菜安、甜菜宁和苯胺灵;氯乙酰苯胺类如甲草胺、乙草胺、丁草胺、吡草胺、异丙草胺、丙草胺、毒草胺;二硝基苯胺类如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类如三氟羧草醚、甲羧除草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆、甲基苯噻隆;羟胺类如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类如咪草烟、咪草酯、灭草烟和灭草喹;腈类如溴苯腈、敌草腈和碘苯腈;氧乙酰胺类如苯噻草胺;磺酰脲类如amidosufuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆和苯黄隆;硫代氨基甲酸酯类如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹、野麦畏;三嗪类如莠去津、氰草津、西玛津、西草净、特丁净;噻嗪酮类如环嗪酮、苯嗪草酮和嗪草酮;其它除草剂如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵膦、草甘膦、isoxaben、哒草特、二氯喹啉酸、喹草酸、草硫膦和灭草环。
此外,本发明活性化合物可以以其商业上可行的制剂和以由这些制剂制备的使用形式存在。这些制剂可以是与增效剂的混合物。增效剂是可以增加活性化合物活性,而所添加的增效剂本身无需有活性的化合物。
由商业上可行的制剂制备的使用形式中的活性化合物的含量可以在相当宽的范围内变化。使用形式的活性化合物浓度可以是按重量计O.O000001至95%的活性化合物,优选在按重量计0.0001至1%间。
使用形式是以适合之的常规形式使用的。
当防治卫生和贮藏产品方面的害虫时,活性化合物的突出之处在于其在木材和陶土上的显著残留作用和对石灰处理过的底物上的碱的良好的稳定性。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如龟甲蜱(schildzecken)、隐喙蜱科、疥螨、恙螨科、(叮咬和吸吮)蝇、寄生蝇幼虫、毛虱、鸟虱和蚤有活性。这些寄生虫包括:虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、虱属(Pediculus spp.)、阴虱属(Phthirus spp.)、盲虱属(Solenoptes spp.)。虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。食毛目及amblycerina和Ischnocerina,例如,毛鸟虱属(Trimenoponspp.)、短角鸟虱属(Menopon spp.)、巨毛虱属(Trinoton spp.)、羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentronspp.、Damalinea spp.、啮毛虱属(Trichodectes spp.)和felicolaspp.。双翅目及长角亚目和短角亚目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyia spp.)、库蚊属(Culicoides spp.)、斑虻属(Chrysopsspp.)、Hybomitra spp.、Atylotus spp.、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、Hydrotaea spp.、螫蝇属(Stomoxys spp.)、血蝇属(Haematobia spp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphora spp.)、绿蝇属(Luciliaspp.)、金蝇属(Chrysomyia spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hippobosca spp.)、lipoptena spp.和羊虱蝇属(Melophagus spp.)。蚤目,例如,蚤属(Pulex spp.)、栉头蚤属(Ctenocephalides spp.)、鼠客蚤属(Xenopsylla spp.)、毛列蚤属(Ceratophyllus spp.)。半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatoma spp.)、红腹猎蝽属(Phodnius spp.)、全圆蝽属(Panstrongylus spp.)。蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、德国小蠊(Blattela germanica)、Suppella spp.。蜱螨目及后气亚目(Metastigmata)和中气亚目(mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、Otabiusspp.、硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、Raillietiaspp.、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostomaspp.)、瓦螨属(Varroa spp.)。Actinedida(后气孔亚目)和Acaridida(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、绵羊疥螨属(Psorergates spp.)、脂螨属(Demodex spp.)、恙螨属(Trombiculaspp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophaus spp.)、嗜木螨属(Caloglyphus spp.)、Hypodectesspp.、翼衣属(Pterolichus spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、Otodectes spp.、疥螨属(Sarcoptesspp.)、Notoedres spp.、鸟疥螨属(Knemidocoptes spp.)、鸡螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.)。
例如,它们对微小牛蜱、Lucilia cuprina和家蝇显示出突出的活性。
本发明式(I)活性化合物也适合防治侵害如下动物的节肢动物:牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、免、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。防治这些节肢动物时,旨在降低死亡和工作中的(与肉、毛、皮、蛋、蜜等等相关)损耗。这样,采用本发明活性化合物使更经济有效的动物管理成为可能。
本发明活性化合物可以使用在兽医方面,使用是以已知的方式,通过外部施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过沐浴或浸蘸、喷雾、浇泼、点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当用于畜禽、家养动物等时,式(I)的活性化合物可以以制剂的形式(例如粉剂、乳剂、流动剂)使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10000倍后施用,或者它们可以以化学浴的形式使用。
另外,现已发现,本发明式(I)化合物对破坏工业材料的昆虫具有强的杀虫作用。可以列举且是优选的昆虫是下列,但不限于这些昆虫:甲虫如家天牛(Hylotrupes bajulus)、Chlorophorus pilosis、具斑窃蠹(Anobium punctatum)、Xestobium rufovillosum、Ptilinuspecticornis、Dendrobium pertinex、Ernobium mollis、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(L.africanus)、平颈粉蠹(L.planicollis)、桴粉蠹(L.linesris)、L.pubescens、Trogoxylon aequale、鳞毛粉蠹(Minthesrugicollis)、小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostyrchus capucins)、Heterobostrychus brunneus、Sinoxylon spec.、竹长蠹(Dinoderusminutus)。革翅目,如小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigastaignus、U.augur。白蚁,如木白蚁(Kalotermes flavicollis)、隐白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermesflavipes)、R.santonecsis、R.lucifugus、澳洲白蚁(Mastotermes darwiniensis)、Zootermopsis nevadensis、家白蚁(Coptotermes formosanus)。衣鱼如西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为无生命的材料如优选的是塑料、胶水、粘性材料、纸和硬纸板、皮革、木材和木制品和涂料。
可防止害虫侵袭的材料特别优选木材和木制品。
可以用本发明的药剂或含有之的组合物保护的木材和木制品应理解为有下列含义,例如,建筑木料、木梁、铁道枕木、桥梁组件、桥形码头、木车、盒、箱、容器、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
本发明活性化合物可以以其原样、以其浓缩物或通常的常规制剂使用。所述的常规制剂是例如可湿性粉剂、颗粒剂、溶液、悬浮剂、乳剂或膏剂。
上述制剂可以以本身已知的方式制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂、需要时的脱水剂和UV稳定剂和需要时的着色剂和染料和其它加工辅助剂相混合。
用于保护木材和木制品的杀虫组合物或浓缩物包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
所采用的药剂或浓缩物的量取决于昆虫的种类和密度,以及介质。所用最佳量可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足矣。
所用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油样溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,且如果需要是乳化剂和/或润湿剂。
所用的有机化学溶剂优选是油性或油样溶剂,所述的溶剂具有大于35的挥发度和高于30℃的闪点,优选高于45℃。用作这种油性或油样溶剂的物质是低挥发性的,且不溶于水,这类物质适合的有矿物油或其芳族馏份且含有矿物油的溶剂混合物,优选是高纯汽油、石油和/或烷基苯。
使用沸程为170到220℃的矿物油、沸程为170到220℃的高纯汽油、沸程为250到350℃的碇子油、沸程为160到280℃的石油或芳族化合物、松节油等等是有利的。
在优选的实施方案中,所用的物质是沸程为180至210℃的液体脂族烃或沸程为180至220℃的芳族和脂族烃的高沸点混合物和/或碇子油和/或单氯萘,优选α-单氯萘。
挥发度高于35且闪点高于30℃,优选高于45℃的低挥发性有机油性或油样溶剂,可以部分地由易挥发或中挥发性的有机化学溶剂替代,其前提条件是,溶剂混合物也具有高于35的挥发度且闪点高于30℃,优选高于45℃,且杀虫剂/杀真菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物或脂族极性有机化学溶剂或溶剂混合物被替代。优选采用的物质是含有羟基和/或酯和/或醚基团的脂族有机化学溶剂,如例如乙二醇醚、酯等。
在本发明范围内使用的有机化学粘合剂是本身已知的粘合干性油和/或合成树脂,它们可以用水稀释和/或在所采用的有机化学溶剂中是可溶的、可分散的或可乳化的,特别是那些由如下组成,或包含如下成分的粘合剂:丙烯酸树酯、乙烯树脂,例如聚乙酸乙烯酯、聚酯树酯、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、苯酚树脂、烃类树脂如茚-香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
用作粘合剂的合成树脂可以以乳液、分散液或溶液的形式使用。沥青或沥青状物质也可以用作粘合剂,其量至多为按重量计10%。此外,可以采用已知的着色剂、染料、防水剂、调味剂和抑制剂或抗腐蚀剂等。
根据本发明,组合物或浓缩物优选含有至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。根据本发明所优选采用的物质是油含量超过按重量计45%,优选50至68%的醇酸树脂。
所有的或部分上述粘合剂可以由固定剂(混合物)或增塑剂(混合物)替代。这些添加剂是旨在防止活性化合物的挥发和结晶或沉淀。它们优选替代0.01至30%的粘合剂(以所用的粘合剂的100%为基准)。
增塑剂来自属于下列化学分类的物质:邻苯二甲酸酯类,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯类,如磷酸三丁酯,己二酸酯类,如二(2-乙基己基)己二酸酯,硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,如油酸丁酯,甘油醚类或高分子量乙二醇醚类、甘油酯类和对甲苯磺酸酯类。
固定剂化学上基于聚乙烯烷基醚类如聚乙烯甲基醚,或酮类如二苯甲酮或亚乙基二苯甲酮。
另一种适合的溶剂或稀释剂是(特别是)水,如果需要是水与一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别有效的木材保护通过工业规模的浸渍工艺,例如真空、双真空或压力工艺的方式获得。
如果需要,直接可用的组合物可以包含其它杀虫剂和(如果需要)也可以有一或多种杀真菌剂。
可能混合于其中的另外的组分优选是WO 94/29268中提到的杀虫剂和杀真菌剂。在上述文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、silafluofin、氟氯氰菊酯、甲体氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、咪呀胺、NI-25、氟虫脲、氟铃脲和杀虫隆,以及杀真菌剂如环氧唑(epoxyconazole)、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、metconazole、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明活性化合物的制备和应用可以参见下列实施例。制备实施例实施例(Ia-1)
将67.3g(0.60mol)叔丁醇钾导入400ml无水二甲基甲酰胺(DMF)中,在0至10℃下,滴加入133.6g(0.40mol)1-(2,4,6-三甲基苯基乙酰基氧基)-4-氧杂-环己基羧酸乙酯的溶液。将此混合物在室温下搅拌过夜。
收集时,将反应混合物缓慢滴加入2升冰冷的1N盐酸中,沉淀物用抽吸滤出,并用水彻底洗涤,产物在真空烘干箱中干燥。
纯化时,将粗产物用正己烷煮沸,再次用抽吸过滤,并干燥。
收率:91.6g(理论值的76%)固体物,熔点:224-226℃。
下列式(Ia)化合物类似地或根据一般的制备说明获得:(在表中采用下列缩写:Me=甲基、Et=乙基、Pr=丙基、Bu=丁基、Ph=苯基)
表5
实施例(Ib-1)
实例号 | A,B | X | Y | Zn | 熔点(℃) |
Ia-2 | -CH2-CH(CH3)-O-(CH2)2- | Me | Me | 6-Me | 235 |
Ia-3 | -CH2-CH(CH3)-O-(CH2)2- | Me | Me | H | |
Ia-4 | -CH2-CH(CH3)-O-(CH2)2- | Cl | Cl | H | |
Ia-5 | -CH2-CH(CH3)-O-(CH2)2- | Cl | H | Cl | |
Ia-6 | -CH2-CH(C2H5)-O-(CH2)2- | Me | Me | 6-Me | 油状物 |
Ia-7 | -CH2-CH(C2H5)-O-(CH2)2- | Me | Me | H | |
Ia-8 | -CH2-CH(C2H5)-O-(CH2)2- | Cl | Cl | H | |
Ia-9 | -CH2-CH(C2H5)-O-(CH2)2- | Cl | H | Cl | |
Ia-10 | -CH2-C(CH3)2-O-(CH2)2- | Me | Me | 6-Me | |
Ia-11 | -CH2-C(CH3)2-O-(CH2)2- | Me | Me | H | |
Ia-12 | -CH2-C(CH3)2-O-(CH2)2- | Cl | Cl | H | |
Ia-13 | -CH2-C(CH3)2-O-(CH2)2- | Cl | H | 6-Cl | |
Ia-14 | -CH2-CH(Me)-O-CH(Me)-CH2- | Me | Me | 6-Me | |
Ia-15 | -CH2-CH(Me)-O-CH(Me)-CH2- | Me | Me | H | |
Ia-16 | -CH2-CH(Me)-O-CH(Me)-CH2- | Cl | Cl | H | |
Ia-17 | -CH2-CH(Me)-O-CH(Me)-CH2- | Cl | H | Cl | |
Ia-18 | -CH2-O-(CH2)3- | Me | Me | 6-Me |
实例号 | A,B | X | Y | Zn | 熔点(℃) |
Ia-19 | -CH2-O-CH(Me)-(CH2)2- | Me | Me | 6-Me | |
Ia-20 | -CH2-O-(CH2)2- | Me | Me | 6-Me | |
Ia-21 | -CH(Me)-O-(CH2)2- | Me | Me | 6-Me | |
Ia-22 | -CH2-O-CH(Me)-CH2- | Me | Me | 6-Me | |
Ia-23 | -CH2-O-CH2-CH(Me)- | Me | Me | 6-Me | |
Ia-24 | -(CH2)2-S-(CH2)2- | Me | Me | 6-Me | 266-267 |
Ia-25 | -(CH2)2-S-(CH2)2- | Me | Me | H | |
Ia-26 | -(CH2)2-S-(CH2)2- | Cl | Cl | H | |
Ia-27 | -CH2-CH(CH3)-S-(CH2)2- | Me | Me | 6-Me | |
Ia-28 | -CH2-CH(CH3)-S-(CH2)2- | Me | Me | H | |
Ia-29 | -CH2-CH(CH3)-S-(CH2)2- | Cl | Cl | H | |
Ia-30 | -CH2-S-(CH2)2- | Me | Me | 6-Me | 122-124 |
Ia-31 | -CH2-S-(CH2)2- | Me | Me | H | |
Ia-32 | -CH2-S-(CH2)2- | Cl | Cl | H | |
Ia-33 | -(CH2)2-N(COMe)-(CH2)2- | Me | Me | 6-Me | 230 |
Ia-34 | -(CH2)2-N(COMe)-(CH2)2- | Me | Me | H | |
Ia-35 | -(CH2)2-N(COMe)-(CH2)2- | Cl | Cl | H | |
Ia-36 | -(CH2)2-O-(CH2)2- | Me | H | 6-Me | |
Ia-37 | -(CH2)2-O-(CH2)2- | Cl | Me | H | 219 |
Ia-38 | -(CH2)2-O-(CH2)2- | Me | Cl | H | |
Ia-39 | -(CH2)2-O-(CH2)2- | Cl | OMe | H | |
Ia-40 | -(CH2)2-O-(CH2)2- | Me | OMe | H | |
Ia-41 | -(CH2)2-O-(CH2)2- | Me | H | 6-OMe |
将28.8g(0.10mol)3-(2,4,6-三甲基苯基)-5,5-亚乙基-氧杂-亚乙基季酮酸按例(Ia-1)导入400ml无水二氯甲烷中,加入15.2g(0.15mol)三乙胺,并在0至10℃下,滴加入15.7g(0.13mol)新戊酰氯溶液。将此混合物在室温下搅拌几小时。
收集时,将反应混合物依次用10%浓度的柠檬酸、碳酸氢钠溶液和水洗涤,有机相经硫酸钠干燥,并蒸发。
纯化时,将粗产物用石油醚搅拌,并用抽吸滤出。
收率:29.4g(理论值的78%)固体物,熔点:119-120℃。
下列式(Ib)至(Ig)化合物类似地或根据一般的制备说明获得:
表6
实例号A,B | X | Y | Zn | R1 | 熔点(℃) | |
Ib-2 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | i-Pr | 122 |
Ib-3 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe2-CH2Cl | 170 |
Ib-4 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe2-i-Pr | 118 |
Ib-5 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CH=CMe2 | 139 |
Ib-6 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | Ph | 147-53 |
Ib-7 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe2-CH2F | 153-55 |
Ib-8 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe(CH2F)2 | 158 |
Ib-9 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe(CH2Cl)2 | 188 |
Ib-10 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | C(CH2Cl)3 | 177 |
Ib-11 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe2-CH2OMe | 177 |
Ib-12 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe(CH2OMe)2 | 104 |
Ib-13 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | C(CH2OMe)3 | 103 |
Ib-14 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe(-CH2-)5 | 157 |
Ib-15 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe(CH2OCH2OCH2) | 176-79 |
Ib-16 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | (CH2)8-CH3 | 油状物 |
Ib-17 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | (CH2)14-CH3 | 油状物 |
Ib-18 | -(CH2)2-O-(CH2)2- | Cl | Cl | H | Me | |
Ib-19 | -(CH2)2-O-(CH2)2- | Me | Me | H | i-Pr | |
Ib-20 | -CH2-CH(Me)-O-(CH2)2- | Me | Me | 6-Me | i-Pr | |
Ib-21 | -CH2-CH(Me)-O-(CH2)2- | Me | Me | 6-Me | CH2-t-Bu | |
Ib-22 | -CH2-CH(Me)-O-(CH2)2- | Me | Me | 6-Me | t-Bu | 130 |
实例号A,B | X | Y | Zn | R1 | 熔点(℃) | |
Ib-23 | -CH2-CH(Me)-O-(CH2)2- | Me | Me | 6-Me | CMe2-CH2Cl | |
Ib-24 | -CH2-CH(Me)-O-CH(Me)-CH2- | Me | Me | 6-Me | t-Bu | |
Ib-25 | -CH2-CH(Et)-O-CH(Me)-CH2- | Me | Me | 6-Me | t-Bu | |
Ib-26 | -CH2-C(CH3)2-O-(CH2)2- | Me | Me | 6-Me | t-Bu | |
Ib-27 | -CH2-O-(CH2)3- | Me | Me | 6-Me | t-Bu | |
Ib-28 | -CH2-O-CH(Me)-(CH2)2- | Me | Me | 6-Me | t-Bu | |
Ib-29 | -CH2-O-(CH2)2- | Me | Me | 6-Me | t-Bu | |
Ib-30 | -(CH2)2-S-(CH2)2- | Me | Me | 6-Me | Me | 198-200 |
Ib-31 | -(CH2)2-S-(CH2)2- | Me | Me | 6-Me | t-Bu | 113-115 |
Ib-32 | -CH2-S-(CH2)2- | Me | Me | 6-Me | Me | 油状物 |
Ib-33 | -CH2-S-(CH2)2- | Me | Me | 6-Me | i-Pr | 108-110 |
Ib-34 | -CH2-S-(CH2)2- | Me | Me | 6-Me | t-Bu | 95-97 |
Ib-35 | -(CH2)2-N(COMe)-(CH2)2- | Me | Me | 6-Me | t-Bu | 68 |
Ib-36 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CH2-CF=CF2 | 油状物 |
Ib-37 | -(CH2)2-O-CHEt-CH2- | Me | Me | 6-Me | t-Bu | 132 |
Ib-38 | -(CH2)2-O-CHEt-CH2- | Me | Me | 6-Me | CH2-t-Bu | 69 |
Ib-39 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | 4-NO2-Ph- | 191-195 |
Ib-40 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | 4-OMe-Ph- | 112-116 |
Ib-41 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe2Et | 130-132 |
Ib-42 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | CMe2CH2OEt | 126-129 |
Ib-43 | -(CH2)2-O-(CH2)2- | Me | H | 6-Me | t-Bu | |
Ib-44 | -(CH2)2-O-(CH2)2- | Cl | Me | H | t-Bu | 128 |
Ib-45 | -(CH2)2-O-(CH2)2- | Me | Cl | H | t-Bu | |
Ib-46 | -(CH2)2-O-(CH2)2- | Cl | OMe | H | t-Bu | |
Ib-47 | -(CH2)2-O-(CH2)2- | Me | OMe | H | t-Bu | |
Ib-48 | -(CH2)2-O-(CH2)2- | Me | H | 6-OMe | t-Bu |
表7
实例号 | A,B | X | Y | Zn | L | M | R2 | 熔点(℃) |
Ic-1 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | O | O | i-Pr | 104-05 |
Ic-2 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | O | O | t-Bu | 107 |
Ic-3 | -CH2-CH(Me)-O-(CH2)2- | Me | Me | 6-Me | O | O | i-Pr | 油状物 |
Ic-4 | -CH2-CH(Me)-O-CH(Me)-CH2- | Me | Me | 6-Me | O | O | s-Bu | |
Ic-5 | -CH2-C(CH3)2-O-(CH2)2- | Me | Me | 6-Me | O | O | i-Pr | |
Ic-6 | -CH2-S-(CH2)2- | Me | Me | 6-Me | O | O | i-Pr | 119-121 |
Ic-7 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | O | O | CH2t-Bu | 145-147 |
Ic-8 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | O | O | i-Bu | 96-98 |
Ic-9 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | O | O | s-Bu | 111-113 |
Ic-10 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | O | S | i-Pr | 103-105 |
表8
式(II)中间体的制备实施例实施例(II-1):
实例号 | A | B | X | Y | Z | R3 | 熔点℃ |
Id-1 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | Me | 171-173 | |
Id-2 | -(CH2)2-O-(CH2)2- | Me | Me | 6-Me | 4-Me-Ph- | 146-148 |
将31.3g(0.18mol)1-羟基-4-氧杂-环己烷羧酸乙酯导入150ml二氯甲烷中,加入21.9g(0.216mol)三乙胺,在0至10℃下滴加入38.9g(0.20mol)基乙酰氯的50ml二氯甲烷溶液。将此混合物在室温下搅拌过夜。
收集时,将反应混合物依次用10%浓度的柠檬酸、碳酸氢钠溶液和水洗涤,有机相经硫酸镁干燥,并蒸发。收率:60.6g油状物(定量)。
下列式(II)化合物类似地或根据一般的制备说明获得:
表9
实施例(XIV-1)
实例号 | A,B | X | Y | Zn | R8 | 熔点(℃) |
II-2 | -CH2-CH(Me)-O-(CH2)2- | Me | Me | 6-Me | Et | 油状物 |
II-3 | -(CH2)2-S-(CH2)2- | Me | Me | 6-Me | Et | 油状物 |
II-4 | -CH2-S-(CH2)2- | Me | Me | 6-Me | Et | 油状物 |
II-5 | -(CH2)2-O-CHMe-CH2- | Me | Me | 6-Me | Et | 油状物 |
II-6 | -(CH2)2-O-CHEt-CH2- | Me | Me | 6-Me | Et | 油状物 |
II-7 | -(CH2)2-(N-COMe)-(CH2)2- | Me | Me | 6-Me | Et | 油状物 |
在-20℃至0℃下,将130g(大致1mol)4-羟基-四氢吡喃-4-甲腈和1050ml无水乙醇的混合物用盐酸饱和。让混合物升至室温,去除过量的HCl,将混合物在真空下浓缩,加入1.5升水,并将此混合物中室温下搅拌3小时。将之过滤,并用二氯甲烷萃取二次。去除溶剂后,获得118g(理论值的61%)4-羟基-四氢吡喃-4-羧酸乙酯,b.p.0.1165℃。
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将严重滋生桃蚜(Myzus persicae)的甘蓝叶(Brassica oleracea)通过浸入所需浓度的活性化合物制剂中来处理。
经过一定的时间后,确定杀死%。100%是指所有的蚜虫均被杀死;0%是指没有蚜虫被杀死。
在此试验中,在实施活性化合物浓度为0.1%的条件下,6天后杀死至少95%的制备实施例化合物有例如下列:Ia-1、Ib-1、Ib-12、Ib-15和Ic-1,而现有技术化合物(B)在活性化合物浓度为0.1%的条件下,只造成70%的死亡。实施例B临界浓度试验/根内吸作用试虫:甜菜蚜溶剂:4份重量的丙酮乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
活性化合物制剂与土壤均匀混合。在制剂中的活性化合物浓度在此处实际上并不重要,只有每单位体积土壤的活性化合物重量(以ppm给出,=mg/l)是关键的。将处理的土壤移入盆中,并于这些盆中种植上蚕豆(Vicia faba)。此活性化合物可以以这种方式通过植物的根从土壤吸收,并转移至叶片。
为证实根内吸效果,8天后,用上述试虫侵食叶片。再过6天后,通过计数或估计死亡的试虫来进行评估。活性化合物的根内吸作用由此死亡率的数字来推算。100%是指所有的试虫均已被杀死,而0%是指所存活的试虫与未处理的情况下所活的试虫数相同。
在此试验中,在实施活性化合物浓度为200ppm的条件下,例如下列制备实施例的化合物显示出100%的活性:Ia-1、Ib-2、Ib-5、Ib-7、Ib-8、Ib-12、Ib-15、Ib-16、Ib-17和Ic-2。实施例C黑尾叶蝉试验溶剂:7份重量的二甲基甲酰胺乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将稻秧(Oryza sativa)通过浸入所需浓度的活性化合物制剂中来处理,当叶片仍润湿时,放上黑尾叶蝉。
经过了所需的时间后,确定杀死%。100%是指所有的黑尾叶蝉均被杀死;0%是指没有黑尾叶蝉被杀死。
在此试验中,在实施活性化合物浓度为0.01%的条件下,6天后杀死100%的制备实施例化合物有例如下列:Ia-1、Ib-1、Ib-16、Ic-1和Ic-3,而现有技术化合物(A)在活性化合物浓度为0.01%的条件下,未造成死亡。实施例D二点叶螨试验(OP抗性)溶剂:3份重量的二甲基甲酰胺乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将严重滋生所有均为发育期二点叶螨(Tetranychus urticae)的豆作物(Phaseolus vulgaris),用所需浓度的活性化合物制剂喷雾。
经过一定的时间后,确定杀死%。100%是指所有的叶螨均被杀死;0%是指没有叶螨被杀死。
在此试验中,在实施活性化合物浓度为0.02%的条件下,7天后杀死至少95%的制备实施例化合物有例如下列:Ia-1、Ia-24、Ib-1、Ib-2、Ib-16、Ib-31和Ic-1,在实施活性化合物浓度为0.1%的条件下,7天后杀死至少98%的制备实施例化合物有例如下列:Ia-5、Ib-7、Ib-11和Ib-22。实施例E苹果全爪螨试验溶剂:3份重量的二甲基甲酰胺乳化剂:1份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
将严重滋生所有均为发育期苹果全爪螨(Panonychus ulmi)的高约30cm的李树(Prunus domestica),用所需浓度的活性化合物制剂喷雾。
经过一定的时间后,确定杀死%。100%是指所有的叶螨均被杀死;0%是指没有叶螨被杀死。
在此试验中,在实施活性化合物浓度为0.02%的条件下,7天后杀死至少95%的制备实施例化合物有例如下列:Ia-1、Ia-24、Ib-1、Ib-2、Ib-16、Ib-31和Ic-1。实施例F蝇幼虫试验/发育抑制作用试虫:均为幼虫期的Lucilia cuprina(OP抗性)[蛹和成虫(未与活性化合物接触)]溶剂:35份重量的乙二醇单甲基醚35份重量的壬基苯酚乙二醇醚
制备适合的制剂时,将3份重量的活性化合物与7份重量的上述溶剂/乳化剂混合物混合,并将此乳油用水稀释至在每种情况下的所需浓度。
对于每一种浓度,将30至50个幼虫转移入玻璃试管中的马肉(1cm3)里,马肉上用吸管移入500μl意欲测试的稀释液。将此玻璃管放置到底部用海沙埋好的塑料烧杯中,并将其保持在培养箱(26±1.5℃、相对湿度70±10%)中。24小时和48小时后,检查活性(杀幼虫作用)。幼虫迁移(大约72小时)后,移出玻璃管,将有孔的塑料盖盖在此烧杯上,在过了1.5倍发育时间(对照蝇羽化)后,计数羽化的蝇并计数蛹数。
作用标准的定义是处理幼虫在48小时后出现死亡(杀幼虫作用)或抑制由蛹羽化成成虫或抑制成蛹。物质的体外作用标准的定义是抑制蝇的发育或在成虫期前的发育阶段停滞不前。100%的杀幼虫作用是指在48小时后所有的幼虫均被杀死。100%发育抑制作用是指无已羽化的成虫。
在此试验中,在实施活性化合物浓度为1000ppm的条件下,例如制备实施例化合物Ia-2、Ia-24、Ib-4、Ia-15、Ib-22、Ib-24和Ib-30各显示出100%作用。
Claims (12)
1.式(I)化合物,
其中
A和B与其所键合的碳原子一起形成未取代或取代的5-或7-元环,
该环中插入至少一个杂原子,
X 代表烷基、卤素或烷氧基,
Y 代表氢、烷基、卤素、烷氧基或卤代烷基,
Z 代表烷基、卤素或烷氧基,
n 代表数字0、1、2或3,
G 代表氢(a)或下列基团之一,
E 代表相应金属离子或铵离子,
L 代表氧或硫,
M 代表氧或硫,
R1 代表烷基、链烯基、烷氧基烷基、烷硫基烷基、多烷氧基烷基,
它们各任选由卤素取代,或代表环烷基,该环烷基可以插入至
少一个杂原子且它任选由卤素、烷基或烷氧基取代,或代表在
每种情况下任选取代的苯基、苯烷基、杂芳基、苯氧基烷基或
杂芳氧基烷基, R2 代表烷基、链烯基、烷氧基烷基或多烷氧基烷基,它们各任选
由卤素取代,或代表环烷基,该环烷基任选由卤素、烷氧基或
烷基取代,或代表在每种情况下任选取代的苯基或苄基,R3、R4和R5相互独立地代表烷基、烷氧基、烷基氨基、二烷基氨
基、烷硫基、链烯基硫基或环烷基硫基,它们各任选由卤素取
代,或代表在每种情况下任选取代的苯基、苄基、苯氧基或苯
硫基,且R6和R7相互独立地代表氢,或代表烷基、环烷基、链烯基、烷氧
基或烷氧基烷基,它们各任选由卤素取代,或代表在每种情况
下任选取代的苯基或苄基,或在一起代表任选由氧或硫插入的
烷二基。
3. 根据权利要求1的式(I)化合物,其中A和B代表C4-C6-烷二基,该烷二基任选由相同或不同的下列取代基单或多取代:卤素、C1-C8-烷基、C3-C8-环烷基、C1-C8-卤代烷基、C1-C6-烷氧基、C1-C6-烷硫基或苯基,且该烷二基中的不直接相邻的一或二个碳原子由下式基团和/或氧和/或硫替代,X 代表C1-C6-烷基、卤素或C1-C6-烷氧基,Y 代表氢、C1-C6-烷基、卤素、C1-C6-烷氧基或C1-C3-卤代烷基,Z 代表C1-C6-烷基、卤素或C1-C6-烷氧基,G 代表氢(a)或下列基团之一:其中E 代表相应金属离子或铵离子,L 代表氧或硫,且M 代表氧或硫,R1代表C1-C20-烷基、C2-C20-链烯基、C1-C8-烷氧基-C1-C8-烷基、C1-C8-烷硫基-C1-C8-烷基或多-C1-C8-烷氧基-C2-C8-烷基,它们各任选由卤素单或多取代,或代表任选由卤素、C1-C6-烷基或C1-C6-烷氧基取代的C3-C8-环烷基且其中不直接相邻的一或二个亚甲基任选由氧和/或硫替代,或代表苯基,该苯基任选由下列基团单至五取代:卤素、硝基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C1-C·6-烷硫基或C1-C6-烷基磺酰基,或代表苯基-C1-C6-烷基,该基团任选由下列基团单至五取代:卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基或C1-C6-卤代烷氧基,或代表吡啶基、噻吩基、呋喃基、吡唑基、嘧啶基或噻唑基,它们各任选由卤素或C1-C6-烷基单或二取代,或代表苯氧基-C1-C6-烷基,该基团任选由卤素或C1-C6-烷基单至三取代,或代表吡啶氧基-C1-C6-烷基、嘧啶氧基-C1-C6-烷基或噻唑氧基-C1-C6-烷基,它们各优选由卤素、氨基或C1-C6-烷基单或二取代,R2 代表C1-C20-烷基、C2-C20-链烯基、C1-C8-烷氧基-C2-C8-
烷基或多-C1-C8-烷氧基-C2-C8-烷基,它们各任选由卤素单或
多取代,
或代表C3-C8-环烷基,该环烷基任选由卤素、C1-C4-烷基或
C1-C4-烷氧基单或多取代,
或代表苯基或苄基,它们各任选由下列基团单至三取代:卤
素、硝基、C1-C6-烷基、C1-C6-烷氧基或C1-C6-卤代烷基,R3 代表任选由卤素单或多取代的C1-C8-烷基,或代表苯基或苄
基,它们各任选下列基团单或多取代:卤素、C1-C6-烷基、
C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基
或硝基,R4和R5相互独立地代表C1-C8-烷基、C1-C8-烷氧基、C1-C8-烷
基氨基、二-(C1-C8-)-烷基氨基、C1-C8-烷硫基、C3-C6-链
烯基硫基或C3-C7-环烷基硫基,它们各任选由卤素单或多取
代,
或代表苯基、苯氧基或苯硫基,它们各任选由下列基团单或多
取代:卤素、硝基、氰基、C1-C4-烷氧基、C1-C4-卤代烷氧
基、C1-C4-烷硫基、C1-C4-卤代烷硫基、C1-C4-烷基或C1-
C4-卤代烷基,R6和R7相互独立地代表氢,或代表C1-C8-烷基、C3-C8-环烷基、
C1-C8-烷氧基、C3-C8-链烯基或C1-C8-烷氧基-C1-C8-烷
基,它们各任选由卤素单或多取代,
或代表苯基或苄基,它们各任选由下列基团单至三取代:卤
素、C1-C8-烷基、C1-C8-卤代烷基或C1-C8-烷氧基,或在一
起代表C2-C6-烷二基,该烷二基任选由氧或硫插入,R9 代表氢、Q、COQ或CO2Q,其中Q 可以是上述业已提到的R2中优选的含义,n 代表0、1或2,
4. 根据权利要求1的式(I)化合物,其中A和B代表C4-C5-烷二基,该烷二基任选由相同或不同的下列取代
基单至四取代:氟、氯、C1-C6-烷基、C3-C6-环烷基、C1-
C6-卤代烷基、C1-C4-烷氧基、C1-C4-烷硫基或苯基,且该烷
二基中的不直接相邻的一或二个碳原子由下式基团或由氧或由硫替代,X 代表C1-C4-烷基、氟、氯、溴或C1-C4-烷氧基,Y 代表氢、C1-C4-烷基、氟、氯、溴、C1-C4-烷氧基或C1-C2卤代烷基,Z 代表C1-C4-烷基、氟、氯、溴或C1-C4-烷氧基,G 代表氢(a)或下列基团之-:其中E 代表相应金属离子或铵离子,L 代表氧或硫,且M 代表氧或硫,R1 代表C1-C16-烷基、C2-C16-链烯基、C1-C6-烷氧基-C1-C6-
烷基、C1-C6-烷硫基-C1-C6-烷基或多-C1-C6-烷氧基-C1-
C6-烷基,它们各任选由氟或氯单至六取代,
或代表C3-C7-环烷基,该环烷基任选由氟、氯、C1-C5-烷基
或C1-C5-烷氧基取代,且该环烷基中的不直接相邻的一或二
个亚甲基任选由氧和/或硫替代,
或代表苯基,该苯基任选由下列基团单至三取代:氟、氯、溴、
硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代烷基、C1-
C3-卤代烷氧基、C1-C4-烷硫基或C1-C4-烷基磺酰基,
或代表苯基-C1-C4-烷基,该基团任选由下列基团单至三取
代:氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代
烷基或C1-C3-卤代烷氧基,
或代表吡啶基、噻吩基、呋喃基、吡唑基、嘧啶基或噻唑基,
它们各任选由氟、氯、溴或C1-C4-烷基单或二取代,
或代表苯氧基-C1-C5-烷基,该基团任选由氟、氯、溴或C1-
C4-烷基单或二取代,
或代表嘧啶氧基-C1-C5-烷基、吡啶氧基-C1-C5-烷基或噻唑氧
基-C1-C5-烷基,它们各优选由氟、氯、溴、氨基或C1-C4-烷
基单或二取代,R2 代表C1-C16-烷基、C2-C16-链烯基、C1-C6-烷氧基-C2-C6-
烷基或多-C1-C6-烷氧基-C2-C6-烷基,它们各任选由氟或氯单
至六取代,
或代表C3-C7-环烷基,该环烷基任选由氟、氯、C1-C3-烷基
或C1-C3-烷氧基单至六取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、
氯、溴、硝基、C1-C4-烷基、C1-C3-烷氧基或C1-C3-卤代烷
基,R3 代表任选由氟或氯单至六取代的C1-C6-烷基,或代表苯基或
苄基,它们各任选下列基团单或二取代:氟、氯、溴、C1-C5-
烷基、C1-C5-烷氧基、C1-C3-卤代烷基、C1-C3-卤代烷氧
基、氰基或硝基,R4和R5相互独立地代表C1-C6-烷基、C1-C6-烷氧基、C1-C6-烷
基氨基、二-(C1-C6-)-烷基氨基、C1-C6-烷硫基、C3-C4-链
烯基硫基或C3-C6-环烷基硫基,它们各任选由氟或氯单至六
取代,
或代表苯基、苯氧基或苯硫基,它们各任选由下列基团单或二
取代:氟、氯、溴、硝基、氰基、C1-C3-烷氧基、C1-C3-卤
代烷氧基、C1-C3-烷硫基、C1-C3-卤代烷硫基、C1-C3-烷基
或C1-C3-卤代烷基,R6和R7相互独立地代表氢,或代表C1-C6-烷基、C3-C6-环烷基、
C1-C6-烷氧基、C3-C6-链烯基或C1-C6-烷氧基-C1-C6-烷
基,它们各任选由氟或氯单至六取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、
氯、溴、C1-C5-烷基、C1-C5-卤代烷基或C1-C5-烷氧基,或
一起代表C2-C6-烷二基,该烷二基任选由氧或硫插入,R9 代表氢、Q、COQ或CO2Q,
其中Q 代表C1-C6-烷基、苯基或苄基,n 代表0或1。
5. 根据权利要求1的式(I)化合物,其中A和B代表C4-C5-烷二基,该烷二基任选由相同或不同的下列取代
基单至三取代:氟、氯、甲基、乙基、正丙基、异丙基、正丁
基、异丁基、仲丁基、叔丁基、环己基、三氟甲基、甲氧基、
甲硫基或苯基,且该烷二基中的一个碳原子由下式基团
或由氧或由硫替代,X 代表甲基、乙基、正丙基、异丙基、氟、氯、溴、甲氧基或乙
氧基,Y 代表氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔
丁基、氟、氯、溴、甲氧基、乙氧基或三氟甲基,Z 代表甲基、乙基、丙基、异丙基、正丁基、异丁基、叔丁基、
氟、氯、溴、甲氧基或乙氧基,G 代表氢(a)或下列基团之一:其中E 代表相应金属离子或铵离子,L 代表氧或硫,且M 代表氧或硫,R1 代表C1-C14-烷基、C2-C14-链烯基、C1-C4-烷氧基-C1-C6-
烷基、C1-C4-烷硫基-C1-C6-烷基或多-C1-C4-烷氧基-C1-
C4-烷基,它们各任选由氟或氯单至三取代,
或代表C3-C6-环烷基,该环烷基任选由下列基团取代:氟、
氯、甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、甲
氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁
氧基或叔丁氧基,且该环烷基中的一个亚甲基任选由氧和/或
硫替代,
或代表苯基,该苯基任选由下列基团单或二取代:氟、氯、溴、
甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基、三
氟甲氧基、甲硫基、乙硫基、甲磺酰基、乙磺酰基或硝基,
或代表苯基-C1-C3-烷基,该基团任选由下列基团单或二取
代:氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧
基、三氟甲基、三氟甲氧基,
或代表噻吩基、呋喃基或吡啶基,它们各任选由氟、氯、溴、
甲基或乙基单或二取代,
或代表苯氧基-C1-C4-烷基,该基团任选由氟、氯、甲基或乙
基单或二取代,
或代表吡啶氧基-C1-C4-烷基、嘧啶氧基-C1-C4-烷基或噻唑氧
基-C1-C4-烷基,它们各任选由氟、氯、氨基、甲基或乙基单
或二取代,R2 代表C1-C14-烷基、C2-C14-链烯基、C1-C4-烷氧基-C2-C6-
烷基或多-C1-C4-烷氧基-C2-C6-烷基,它们各任选由氟或氯单
至三取代,
或代表C3-C6-环烷基,该环烷基任选由氟、氯、甲基、乙基、
丙基、异丙基或甲氧基单至三取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、
氯、硝基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基或三
氟甲基,R3 代表任选由氟或氯单至三取代的甲基、乙基、丙基或异丙基,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、
氯、溴、甲基、乙基、丙基、异丙基、叔丁基、甲氧基、乙氧
基、异丙氧基、叔丁氧基、三氟甲基、三氟甲氧基、氰基或硝
基,R4和R5相互独立地代表C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷
基氨基、二-(C1-C4-)-烷基氨基或C1-C4-烷硫基,它们各任
选由氟或氯单至三取代,
或代表苯基、苯氧基或苯硫基,它们各任选由下列基团单或二
取代:氟、氯、溴、硝基、氰基、C1-C2-烷氧基、C1-C2-氟
代烷氧基、C1-C2-烷硫基、C1-C2-氟代烷硫基、C1-C2-烷基
或C1-C2-氟代烷基,R6和R7相互独立地代表氢,或代表C1-C4-烷基、C3-C6-环烷基、
C1-C4-烷氧基、C3-C4-链烯基或C1-C4-烷氧基-C1-C4-烷
基,它们各任选由氟或氯单至三取代,
或代表苯基或苄基,它们各任选由下列基团单或二取代:氟、
氯、溴、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基,或
一起代表C2-C6-烷二基,该烷二基任选由氧或硫插入,R9 代表氢、Q、COQ或CO2Q,其中
Q 代表C1-C4-烷基、苯基或苄基,和
n 代表0或1。
6. 一种制备根据权利要求1的式(I)化合物的方法,其特征在于,
(A)式(Ia)的化合物,其中A、B、X、Y、Z和n具有权利要求1中给出的含义,如下获得:使式(II)的羧酸酯,其中A、B、X、Y、Z和n具有上述含义,且R8 代表烷基,在稀释剂存在下和在碱存在下,进行分子内缩合反应;或(B)式(Ib)化合物,其中A、B、X、Y、Z、R1和n具有权利要求1中给出的含义,如下获得:使式(Ia)化合物,A、B、X、Y、Z和n具有上述含义,α)如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(III)酰基卤反应,其中R1具有上述含义,且Hal 代表卤素,或β)如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(IV)的羧酸酐反应,R1-CO-O-CO-R1 (IV)其中R1 具有上述含义;或(C)式(Ic-1)化合物,其中A、B、X、Y、Z、R2和n具有权利要求1给出的含义且M 代表氧或硫,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(V)的氯甲酸酯或氯甲酸硫酯反应,
R2-M-CO-Cl (V)其中R2和M具有上述含义;或(D)式(Ic-2)化合物,其中A、B、R2、X、Y、Z和n具有权利要求1中给出的含义,且M代表氧或硫,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,α)如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(VI)氯单硫代甲酸酯或氯二硫代甲酸酯反应,其中M和R2具有上述含义;或β)如果需要在稀释剂存在下和如果需要在碱存在下,与二硫化碳,且之后与式(VII)的烷基卤反应,
R2-Hal (VII)其中R2 具有上述含义且Hal 代表氯、溴或碘;或(E)式(Id)化合物其中A、B、X、Y、Z、R3和n具有权利要求1中给出的述含义,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(VIII)的磺酰氯反应,
其中
A、B、L、X、Y、Z、R4、R5和n具有权利要求1中给出的含义,
如下获得:
使式(Ia)化合物其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(IX)的磷化合物反应,其中L、R4和R5具有上述含义和Hal 代表卤素;或(G)式(If)化合物,其中A、B、X、Y、Z和n具有上述含义, 且E 代表相应金属离子或铵离子,如下获得:使式(Ia)化合物,其中A、B、X、Y、Z和n具有上述含义,如果需要在稀释剂存在下,与式(X)或(XI)的金属化合物和胺反应,其中Me 代表一或二价金属,t 代表数字1或2,R10、R11和R12相互独立地代表氢或烷基和R13 代表氢、羟基或C1-C4-烷氧基;或(H)式(Ig)化合物,其中A、B、L、X、Y、Z、R6、R7和n具有权利要求1中给出的含义,如下获得:使式(Ia)化合物,A、B、X、Y、Z和n具有上述含义,α)如果需要在稀释剂存在下和如果需要在催化剂存在下,与式(XII)化合物反应,
R6-N=C=L (XII)其中L和R6具有上述含义;或β)如果需要在稀释剂存在下和如果需要在酸结合剂存在下,与式(XIII)的氨基甲酰氯或硫代氨基甲酰氯类化合物反应,
其中
L、R6和R7具有上述含义。
7.式(II)化合物,
其中
A、B、X、Y、Z和n具有权利要求1中给出的含义且
R8 代表烷基。
9.农药,其特征在于,它们含有至少一种根据权利要求1的式(I)化合物。
10.权利要求1的式(I)化合物防治害虫的应用。
11.防治害虫的方法,其特征在于,使权利要求1的(I)化合物作用于害虫或其环境。
12.制备农药的方法,其特征在于,将权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
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DE19540736A DE19540736A1 (de) | 1994-12-23 | 1995-11-02 | 3-Aryl-tetronsäure-Derivate |
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ATE177093T1 (de) * | 1993-07-05 | 1999-03-15 | Bayer Ag | Substituierte aryl-ketoenolheterocyclen |
ES2127859T3 (es) * | 1993-09-17 | 1999-05-01 | Bayer Ag | Derivados de la 3-aril-4-hidroxi-3-dihidrofuranona. |
DE4431730A1 (de) * | 1994-02-09 | 1995-08-10 | Bayer Ag | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
-
1995
- 1995-12-11 AU AU43420/96A patent/AU4342096A/en not_active Abandoned
- 1995-12-11 BR BRPI9510256-6A patent/BR9510256B1/pt not_active IP Right Cessation
- 1995-12-11 CN CN95197629A patent/CN1079798C/zh not_active Expired - Fee Related
- 1995-12-11 HU HU9801213A patent/HUT77880A/hu unknown
- 1995-12-11 ES ES95942100T patent/ES2190790T3/es not_active Expired - Lifetime
- 1995-12-11 US US08/860,106 patent/US5830825A/en not_active Expired - Lifetime
- 1995-12-11 MX MX9704646A patent/MX9704646A/es not_active IP Right Cessation
- 1995-12-11 WO PCT/EP1995/004869 patent/WO1996020196A1/de active IP Right Grant
- 1995-12-11 EP EP95942100A patent/EP0799228B1/de not_active Expired - Lifetime
- 1995-12-11 DE DE59510597T patent/DE59510597D1/de not_active Expired - Lifetime
- 1995-12-11 PL PL95322741A patent/PL322741A1/xx unknown
- 1995-12-11 CA CA002208375A patent/CA2208375A1/en not_active Abandoned
-
1998
- 1998-08-13 US US09/133,522 patent/US6051723A/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102439013A (zh) * | 2009-05-19 | 2012-05-02 | 拜尔农作物科学股份公司 | 螺杂环特窗酸衍生物 |
WO2010135914A1 (en) * | 2009-05-26 | 2010-12-02 | Syngenta Participations Ag | New spiroheterocyclic furan and thiofuran dione derivatives |
CN102448964A (zh) * | 2009-05-26 | 2012-05-09 | 先正达参股股份有限公司 | 新型螺杂环呋喃和噻吩衍生物 |
US8574607B2 (en) | 2009-05-26 | 2013-11-05 | Syngenta Crop Protection, Inc. | Spiroheterocyclic thiofuran dione derivatives |
Also Published As
Publication number | Publication date |
---|---|
HUT77880A (hu) | 1998-09-28 |
EP0799228B1 (de) | 2003-03-19 |
US5830825A (en) | 1998-11-03 |
DE59510597D1 (de) | 2003-04-24 |
MX9704646A (es) | 1997-09-30 |
EP0799228A1 (de) | 1997-10-08 |
CN1079798C (zh) | 2002-02-27 |
WO1996020196A1 (de) | 1996-07-04 |
BR9510256A (pt) | 1997-11-04 |
CA2208375A1 (en) | 1996-07-04 |
AU4342096A (en) | 1996-07-19 |
ES2190790T3 (es) | 2003-08-16 |
US6051723A (en) | 2000-04-18 |
PL322741A1 (en) | 1998-02-16 |
BR9510256B1 (pt) | 2010-08-10 |
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