CN1200108A - 酯类 - Google Patents
酯类 Download PDFInfo
- Publication number
- CN1200108A CN1200108A CN96197628A CN96197628A CN1200108A CN 1200108 A CN1200108 A CN 1200108A CN 96197628 A CN96197628 A CN 96197628A CN 96197628 A CN96197628 A CN 96197628A CN 1200108 A CN1200108 A CN 1200108A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- formula
- represents hydrogen
- alkoxy
- optionally
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 30
- 229910052736 halogen Chemical group 0.000 claims abstract description 19
- 150000002367 halogens Chemical group 0.000 claims abstract description 17
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 10
- -1 aliphatic radical Chemical class 0.000 claims description 153
- 150000001875 compounds Chemical class 0.000 claims description 80
- 150000002431 hydrogen Chemical class 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000007970 thio esters Chemical class 0.000 claims description 14
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 13
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- LIIBSISAILMKHT-UHFFFAOYSA-N 1-fluorobut-1-en-1-ol Chemical compound CCC=C(O)F LIIBSISAILMKHT-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229910006069 SO3H Inorganic materials 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 150000003009 phosphonic acids Chemical class 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 241000256248 Spodoptera Species 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 241000244206 Nematoda Species 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 241001558017 Gynura Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241000255925 Diptera Species 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 7
- 241000935116 Phaea Species 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 6
- 241000258937 Hemiptera Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000985245 Spodoptera litura Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 5
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- 208000028454 lice infestation Diseases 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PCYKQGRAPGQQCB-UHFFFAOYSA-N 3,4,4-trifluorobut-3-en-1-ol Chemical compound OCCC(F)=C(F)F PCYKQGRAPGQQCB-UHFFFAOYSA-N 0.000 description 4
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 4
- GQCQMFYIFUDARF-UHFFFAOYSA-N 4-bromo-1,1,2-trifluorobut-1-ene Chemical compound FC(F)=C(F)CCBr GQCQMFYIFUDARF-UHFFFAOYSA-N 0.000 description 4
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- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 4
- 239000005775 Fenbuconazole Substances 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000238675 Periplaneta americana Species 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- 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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Abstract
本发明提供新的式(Ⅰ)的酯、制备其的方法及其用于防治动物害虫的应用,其中R1代表氢或卤素,且Q代表或者右上式,ZR9或Z(P-W)R10R11,其中R2、R3、R9、R10、R11、Z和W各如说明书中所定义。
Description
本发明涉及新的酯类、其制备方法及其防治动物害虫的应用,特别是在农业、森林、贮藏产品和材料保护和卫生方面中遇到的昆虫、蜱螨和线虫的应用。
业已知道,4-氯苯甲酸(3,4,4-三氟丁-3-烯基)酯具有杀线虫活性(参见,例如US-4 952 580)。然而,这些化合物的效力和活性谱,特别是在低施用量和浓度下,并不总是令人完全满意。
因此,本发明提供新的式(I)的酯及其盐其中R1代表氢或卤素,且Q代表或者
a)
其中 ,
R2代表氢、硝基、氰基、卤素、烷基、烷氧基、烷硫基或任选取代的芳基且
R3代表COOH、SO3H、NR4R5或OR6,其中
R4代表氢、烷基或任选取代的芳基,
R5代表氢、烷基、任选取代的芳基或COR7,
R6代表氢、任选取代的芳烷基、CONR4R5或COR7,
R7代表烷基、链烯基、任选取代的芳基或NR4R8,且
R8代表氢、烷基或任选取代的芳基,或者
b)是ZR9或Z(P=W)R10R11,其中
Z代表具有一至四个碳原子的脂族基团,其条件是,如果Z代表CH2,则R9不代表苯基,
W代表氧或硫,
R9α)代表芳族基团或代表杂环基基团(如选自吡唑基、咪唑基、三唑基、吗啉基、哌啶基、哌嗪基或吡咯烷基的环状基团),它们各任选由至少一个选自下列的取代基取代:氰基,三甲基甲硅烷基,羟基,烷基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团,
β)代表氢,OR12,SR12,卤素,NR12R13,氰基,三甲基甲硅烷基,硝基,苯基,磺酸或其酯、酰胺或硫酯的基团或代表脂族基团,该脂族基团任选由至少一个选自下列的基团取代:氰基,三甲基甲硅烷基,羟基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,苯基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团,
其中
R12和R13相互独立地各代表
i)氢,
ii)具有一至十二个碳原子的脂族基团或芳族或杂环基基团,它们各任选由至少一个选自下列的基团取代:具有一至四个碳原子的烷基,氰基,三甲基甲硅烷基,羟基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,苯基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团,
iii)或R12或R13与相连的氮原子一起形成氨基酸的一部
分,或如果R12代表氢,或脂族或芳族基团,它们各任选由至少一个选自下列的取代基取代:具有1至4个碳原子的烷基,羟基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团,或苯基,那么R13还代表OR16、COR16、COOR21、NR16R17、SO2R18、P(=O)R19R20,其中R16和R17相互独立地各代表氢、烷基或芳基,R18代表氢、烷基、卤代烷基或芳基,R19和R20相互独立地代表氢、烷基、芳基、烷基、烷硫基、芳硫基、烷基氨基、二烷基氨基、芳基氨基或OR21,且R21代表氢、烷基或芳基,R10和R11相互独立地各代表R22、OR22、SR22或NR22R23,其中R22和R23相互独立地各代表氢,或脂族或芳族基团,它们各任选由至少一个选自下列的取代基取代:氰基,三甲基甲硅烷基,羟基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,苯基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团。
如果式(I)化合物含有能够形成盐的官能团,则它还可以以盐存在。这些官能团包括例如羧基或羟基。适合的阳离子是例如碱金属和碱土金属离子如钠、钙、钾和镁的离子,季铵离子如铵离子本身,以及单-、二-和三烷基铵离子如异丙基铵离子,还有例如吡啶鎓。
包括基团Q的含义,获得下列式(Ia)、(Ib-1)或(Ib-2)化合物:CF2=CR1-CH2-CH2-O-CO-ZR9 (Ib-1)CF2=CR1-CH2-CH2-O-CO-Z(P=W)R10R11 (Ib-2)其中R1、R2、R3、R9、R10、R11、Z和W各如上所定义。
取决于取代基的性质,式(I)化合物可以以几何和/或光学异构体或各种组分的异构体混合物存在。本发明涉及纯异构体和异构体混合物二者。
再者,现已发现,可以如下获得式(Ia)化合物:A)在稀释剂存在下,使式(II)苯甲酸衍生物与式(III)的氟丁烯基溴反应其中X(+)代表碱金属离子或铵离子,且R2和R3各如上所定义,其中R1如上所定义,或者B)如果适宜在碱存在下,且如果适宜在稀释剂存在下,使式(IV)的靛红酸酐与式(V)的氟丁烯醇反应,其中R2、R3和R4各如上定义,
其中
其中
R1如是所定义。
式(Ib)((Ib-1)和(Ib-2))化合物可以通过一般已知的方法制备。所需的起始原料可以容易地通过已知的方法制备和/或是市售的。
最后,已发现,新的式(I)的酯具有非常突出的生物性能,且特别适合于防治动物害虫,特别是在农业、森林、贮藏产品和材料保护和卫生方面中遇到的昆虫、蜱螨和线虫。
式(Ia)提供本发明芳基羧酸酯的一般定义。
上下文提到的化学式中所列的优选取代基或基团范围说明如下:R1优选代表氢、氟、氯或溴。R2优选代表氢,硝基,氰基,氟,氯,溴,C1-C8-烷基,C1-C6-烷氧基,C1-C6-烷硫基,或任选氰基-、氟-、氯-、溴-或C1-C6-烷氧基-取代的苯基。R3优选代表2-COOH、2-SO3H、NR4R5或OR6。R4优选代表氢,C1-C8-烷基,或任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基。R5优选代表氢,C1-C8-烷基,任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基或代表COR7。R6优选代表氢,任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基-C1-C6-烷基或代表CONR4R5或COR7。R7优选代表C1-C8-烷基,C2-C6-链烯基,任选氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基或代表NR4R8。R8优选代表氢,C1-C8-烷基,或任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基。R1特别优选代表氢或氟。R2特别优选代表氢,硝基,氰基,氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,或任选氟-、氯-或C1-C4-烷氧基-取代的苯基。R3特别优选代表2-COOH、2-SO3H、NR4R5或OR6。R4特别优选代表氢,C1-C4-烷基,或任选氟-、氯-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基。R5特别优选代表氢,C1-C4-烷基,任选氟-、氯-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基或代表COR7。R6特别优选代表氢,任选氟-、氯-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基或代表CONR4R5或COR7。R7特别优选代表C1-C4-烷基,C2-C6-链烯基,任选氟-、氯-或C1-C4-烷基-取代的苯基或代表NR4R8。R8特别优选代表氢,C1-C4-烷基,或任选氟-、氯-、C1-C4-烷基或C1-C4-烷氧基-取代的苯基。
最优选的一组式(I)化合物是这样的一组式(I)化合物,其中R1代表氟,R2代表氢且R3代表基团NR4R5。
对于式(Ib)化合物的定义而言,下列是适合的:
术语“卤素”单独或在与其它基团组合中代表氟、氯、溴和碘。
术语“烷基”代表一至约七个碳原子的直链或支链基团。
术语“低级烷基”代表具有一至约四个碳原子的基团。
术语“脂族”代表具有一至约十个碳原子的或如上所定义的饱和或不饱和烷基基团,或代表二至约十个碳原子的或如上所定义的直链或支链链烯基基团。
术语“烷氧基”代表经氧连接的低级烷基基团。
术语“烷硫基”代表经硫连接的低级烷基基团。
术语“烷氧基羰基”代表羧酸的低级烷基酯。
术语“羧酸、磺酸、磷酸、膦酸或上述酸之一的酰胺、酯或硫酯的基团”代表一脂族基团,其中至少一个(优选一个)碳原子由羧基基团(COOH)、磺酸基团、磷酸基团或膦酸基团或由所提到酸之一的低级烷基酯、酰胺或低级烷基硫酯代替。
术语“氨基酸”代表任一具有由-C原子隔开的氨基基团和酸基团的化合物。这些氨基酸包括天然氨基酸,且也包括那些在中心碳原子上具有其它取代基的氨基酸。
术语“烷基-或芳基磺酰胺”代表由低级烷基基团或苯基基团取代的磺酰胺基团,而上述取代基本身可以被取代。
术语“芳族基团”或“芳基”代表如上所定义的任选取代的苯基。
术语“杂环”代表含有至少一个不是碳的元素作为环成员的任一环状化合物。该环可以是饱和的或不饱和的。杂原子可以是氧、氮、硫或另一种元素。杂环包括例如下列基团:噻二唑、吡啶、噻唑、异噻唑、噁唑、咪唑、吡唑、三唑、苯并噻唑、吗啉、哌啶、哌嗪和吡咯烷,且它们各可以由至少一个选自下列的取代基取代:磺酸、磷酸、膦酸、这些酸之一的酯、酰胺或硫酯的基团,氰基,三甲基甲硅烷基,羟基,烷氧基,卤素,硝基,氨基,巯基,烷硫基,羧基,烷氧基羰基和苯基。
在本文提到的式(Ib)化合物中,非常特别优选的式(Ib)化合物是N-[(1,1-二甲基乙氧基)羰基]-L-丙氨酸(3,4,4-三氟-3-丁烯基)酯。
上面提到的一般或优选的基团定义或说明适合于终产物,且因此适合于起始原料和中间体。这些基团的定义可以按需要相互组合,即,包括分别优选的范围间的组合。
式(Ia)化合物中,优选的是那些含有上面作为优选给出的含义的组合的式(Ia)化合物。
式(Ia)化合物中,特别优选的是那些含有上面作为特别优选给出的含义的组合的式(Ia)化合物。
在上下文给出的基团定义中,烃基如烷基或链烯基——包括在与杂原子的组合如烷氧基或烷硫基中——是直链或其可能的支链。
根据方法C),使用例如邻苯二甲酸酐与3,4,4-三氟丁-3-烯-1-醇作为起始原料,用于制备式(Ia)化合物时,反应的途径可以用下列反应式来代表:
上面描述的制备式(Ia)化合物的方法A)的特征在于,将式(II)的苯甲酸衍生物与式(III)的氟丁烯基溴在稀释剂存在下进行反应。
合适的稀释剂特别是有机溶剂,例如任选氯代的芳族烃如甲苯、二甲苯或氯苯,醚类如二噁烷或四氢呋喃,腈类如乙腈,亚砜类如二甲基亚砜,酰胺类如二甲基甲酰胺或羧酸酯类如乙酸乙酯。
方法A)中的反应温度可以在相对宽的范围内变化。通常,反应是在0℃至160℃间,优选在20℃至120℃间的温度下进行。
式(II)化合物与式(III)化合物的摩尔比通常是2∶1至1∶2。
反应通常是在常压下进行的。
后处理时,将反应混合物例如水解,并将产物用有机溶剂如乙酸乙酯、二氯甲烷或甲苯萃取,随后去除溶剂。
上面描述的制备式(Ia)化合物的方法B)的特征在于,将式(IV)的靛红酸酐与式(V)的氟丁烯醇反应,如果适宜,反应在稀释剂和碱存在下进行。
适合于此反应的稀释剂是所有的常规溶剂。
优选的是使用任选卤代的脂族或芳族烃如环己烷、甲苯、二甲苯、二氯甲烷、氯仿、二氯乙烷或氯苯或醚类如四氢呋喃或二噁烷。
此反应也可以在无上述溶剂之一存在下进行。在这种情况下,采用过量的式(V)氟丁烯醇或许会是有利的。
在碱存在下进行本发明方法B)或许会是有利的。
优选的是使用胺,优选是叔胺如三乙胺、吡啶或二氮杂二环十一碳烯(DBU)或无机碱,例如碱金属碳酸盐、碳酸氢盐或氢氧化物如碳酸钾、碳酸氢钠或氢氧化钠。
采用催化量的碱已足矣。
方法B)中的反应温度可以在相对宽的范围内变化。通常,反应是在0℃至180℃间,优选在20℃至140℃间的温度下进行。
式(IV)化合物与式(V)化合物的摩尔比通常是1∶2至2∶1。反应通常是在常压下进行的。
后处理时,将反应混合物例如水解,并将产物用有机溶剂如乙酸乙酯、二氯甲烷或甲苯萃取,随后去除溶剂。
制备式(Ia)化合物的方法C)的特征在于,将式(VI)的酸酐与式(V)的氟丁烯醇反应,如果适宜,反应在稀释剂和碱存在下进行。
关于稀释剂、碱、反应的实施及后处理,给予方法B)的说明也同样适合。
方法A)需要的起始原料式(II)苯甲酸衍生物可以用简单的已知方法,通过相应的苯甲酸(它是易于制备的且其大部分是市售的)与碱(例如碱金属氢氧化物例如氢氧化锂、氢氧化钾或氢氧化钠或胺如二甲胺、三乙胺或丁胺)反应而制备。
方法A)需要的另一起始原料式(III)氟丁烯基溴是已知的和/或可以通过已知的方法以简单地方式制备(参见,C.A.119,94 942)。
方法B)需要的起始原料式(IV)靛红酸酐是已知的和/或可以通过已知的方法以简单地方式制备(参见,Methoden der Organ.Chemie-Houben-Weyl,Vol.4E,p.214ff(1983))。
方法A)需要的另一起始原料式(V)氟丁烯醇是已知的和/或可以通过已知的方法以简单的方式制备(参见,例如WO 92/15 555)。
方法C)需要的起始原料式(VI)酸酐是已知的和/或可以通过已知的方法以简单地方式制备(参见,Methodicum Chimicum,C-Ocompouds,Vol. 5,p.614ff(1975))。
本发明活性化合物适合防治动物害虫,特别是在农业、森林、贮藏产品和材料保护以及卫生方面上遇到的昆虫、蜱螨和线虫。它们对正常敏感和抗性种类和对所有或一些生长发育阶段有活性。上述害虫包括:等足目,例如,潮虫(Oniscus asellus)、平甲虫(Armadillidium vulgare)和斑鼠妇(Porcellio scaber)。倍足目,例如,具斑马陆(Blaniulus guttulatus)。唇足目,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigeraspec)。综合目,例如,庭院幺蚰(Scutigerella immaculata)。缨尾目,例如,西洋衣鱼(Lepisma saccharina)。弹尾目,例如,具棘跳虫(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(Gryllotalpa spp.)、热带飞蝗(Locusta migratoria migratorioids)、殊种蚱蜢(Melanoplusdifferentialis)和沙漠蝗(Schistocerca gregaria)。革翅目,例如,欧洲球螋(Forficula aurieularia)。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.)和畜属虱(Damalineaspp.)。缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thripstabaci)。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)、长红猎蝽(Rhodnius 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)、茶藨隐瘤蚜(Cryptomyzusribis)、甜菜蚜(Aphis fabae)、苹果蚜(Doralis pomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterus arundinis)、美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodonhumili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoascaspp.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettixcincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetiaoleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvatalugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotushederae)、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)、苹细蛾(Lithocolletisblancardella)、苹果巢蛾(Hyponomeuta padella)、小菜蛾(Plutellamaculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctischrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrixthurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotisspp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Eariasinsulana)、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)、灰翅夜蛾属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pierisspp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestia kuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineola bisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoecia podana)、织网衣蛾(Capua reticulana)、云松卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)。鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、Bruchidius obtectus、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsa decemlineata)、辣根猿叶甲(Phaedoncochleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodeschrysocephala)、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(Ceuthorrhynchus assimilis)、苜蓿叶象虫(Hyperapostica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctusspp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptus hololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Tribolium spp.)、黄粉虫(Tenebrio molitor)、叩头虫属(Agriotesspp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)和褐新西兰肋翅鳃角金龟(Costelytra zealandica)。膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(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(Muscaspp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophora erythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebraspp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibiohortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbia spp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitis capitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。蚤目,例如,印鼠客蚤(Xenopsylla cheopis)、毛列蚤属(Ceratophyllusspp.)和猫栉头蚤(Ctenocephalides felis)。蛛形目,例如,蝎(scorpio maurus)和毒寇蛛(Latrodectus mactans)。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(Amblyommaspp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptesspp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychus spp.)。植物寄生线虫包括例如垫刃线虫(Pratylenchus spp.)、毕肖穿孔线虫(Radopholus similis)、Ditylenchus dipsaci、Tylenchulussemipenetrana、异皮线虫(Heterodera spp.),囊线虫(Globoderaspp.)、根结线虫(Meloidogyne spp.)、滑刃线虫(Aphelechoides spp.)、Longidorus spp.、剑线虫(Xiphinema spp.)和髦根线虫(Trichodorusspp.)。
本发明式(I)活性化合物具有特别突出的杀线虫活性,例如,对黄麻根结线虫(Meloidogyne incognita)。
它们也具有良好的叶面杀虫活性。
本活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、水溶性粉剂、颗粒剂、悬浮乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
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(即液体和/或与固体载体)混合,且如果适宜与表面活性剂(即乳化剂和/或分散剂和/或起泡剂)混合。
在用水作填充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有: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基亚砜,以及水。
合适的固体载体是:
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:例如压碎并分级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羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,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、钼和锌的盐。
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、苯基脲类和由微生物生产的物质,及其它。
在混合物的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、甲羟异噁唑、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、稻瘟酯、戊菌唑、戊菌隆、稻病磷、稻瘟酞、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、稻纹散、乙烯菌核利、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。杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC 303 630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿维菌素(avermectin)、AZ 60541、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、CGA 157 419、CGA 184 699、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、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、NC 184、NI 25、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、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH 5992、水杨硫磷、硫线磷、施乐宝(silafluofen)、治螟磷、甲丙硫磷、米满(tebufenozide)、吡螨胺(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。
也可以是与其它已知活性化合物如除草剂或与化肥和生长调节剂的混合物。
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0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
化合物是以适合于使用形式的常规形式采用的。
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)如硬蜱、隐喙蜱科、疥螨、恙螨科、(叮咬和吸吮)蝇、寄生蝇幼虫、虱、头虱、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(Linognathus spp.)、虱属(Pediculus spp.)、阴虱属(Phthirus spp.)和盲虱属(Solenoptesspp.)。食毛目及amblycerina和细角亚目,例如,毛鸟虱属(Trimenoponspp.)、短角鸟虱属(Menopon spp.)、豆羽虱属(Trinoton spp.)、羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalinea spp.)、啮毛虱属(Trichodectes spp.)和猫虱属(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(Lutzomyiaspp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、齿股蝇属(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.)、蜱蝇属(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.)和毛列蚤属(Ceratophyllus spp.)。半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatoma spp.)、红腹猎蝽属(Rhodnius spp.)和全圆蝽属(Panstrongylus spp.)。蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、德国小蠊(Blattela germanica)和棕带蠊属(Suppellaspp.)。螨亚纲及后气亚目(Metastigmata)和中气亚目(mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、残喙蜱(Otabiusspp.)、硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、苹蜱属(Dermacentor spp.)、血蜱属(Haemaphysalisspp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostoma spp.)和瓦螨属(Varroaspp.)。Actinedida(后气孔亚目)和粉螨目(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.)、蠕形螨属(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.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、瘙螨属(Psoroptesspp.)、痒螨属(Chorioptes spp.)、耳癞螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、痂螨属(Notoedres spp.)、疙螨属(Knemidocoptesspp.)、胞螨属(Cytodites spp.)和皮膜螨属(Laminosioptes spp.)。
例如,它们对微小牛蜱和铜绿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、兔、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,旨在降低死亡和增加产量(与肉、毛、皮、蛋、蜜等等相关)。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,例如通过沭浴或浸蘸、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、悬浮剂)的使用,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。
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1
将于300毫升甲苯中的50.5克(0.31摩尔)靛红酸酐与1克4-二甲基氨基吡啶、0.1克碳酸钾和44.1克(0.35摩尔)3,4,4-三氟丁-3-烯-1-醇一起加热回流15小时。冷却后,将反应混合物用水洗涤,减压去除甲苯。获得67.7克2-氨基苯甲酸(3,4,4-三氟丁-3-烯-1-基)酯,为清澈油状物。
收率:理论值的89.1%。
log p*(pH2)=3.05;n20 D=1.5160。
将于100毫升二甲基亚砜中的32克(0.2毫升)水杨酸钠与28.4克(0.15摩尔)1-溴-3,4,4-三氟丁-3-烯一起加热至50℃保持15小时。冷却后,将反应混合物用水稀释,将产物用二氯甲烷萃取,有机相减压浓缩。随后将残留物减压蒸馏。获得无色的24.3克(收率:理论值的65.8%)2-羟基-苯甲酸(3,4,4-三氟丁-3-烯-1-基)酯,熔点102-108℃/1.5毫米。
*log P:正辛醇/水分配系数的十为基数的对数,通过使用H2O/CH3CN的反相HPLC分析确定。
式(Ib)化合物的实施例实施例23
将于35毫升乙腈中的2克(0.01摩尔)O,O-二乙基膦酰基乙酸和1.52克DBU(二氮杂二环十一碳烯)与2.5克(0.12摩尔)4-溴-1,1,2-三氟-丁-1-烯混合,将此混合物在60℃下搅拌7小时。之后将反应混合物倒入水中,并用乙醚萃取二次。合并的醚相用水洗涤,用浓度5%的NaOH水溶液洗涤二次,之后再用水洗涤二次。蒸发醚,给出0.93克O,O-二乙基膦酰基乙酸(3,4,4-三氟丁-3-烯基)酯,为清澈的液体。
元素分析:计算值:C 39.48;H 5.30
实测值:C 38.97;H 5.24实施例24
伴随冰冷却,将于6毫升乙腈中的4.9毫升(0.037摩尔)三甲基甲硅烷基溴滴加入到于8毫升乙腈中的0.93克(0.0031摩尔)实施例23化合物中,之后将混合物在室温下搅拌过夜。随后将混合物减压浓缩,残留物与甲醇混合。将混合物在室温下搅拌30分钟,减压去除甲醇。将残留物溶解于乙醚中。减压去除乙醚,给出0.71克膦酰基乙酸(3,4,4-三氟丁-3-烯基)酯,为粘性浅黄色油状物。
元素分析: 计算值:C 27.64;H 3.63
在室温下,将98克(0.52摩尔)4-溴-1,1,2-三氟丁-1-烯滴加入到于400毫升乙腈中的50克(0.37毫升)苯乙酸和55.9克(0.37摩尔)DBU中。将混合物在室温下搅拌几小时,回流过夜,之后在室温下再搅拌2天。减压去除溶剂,将残留物与水混合,用乙醚萃取。醚相用浓度5%的NaOH水溶液洗涤二次,用水洗涤二次,经硫酸镁干燥,蒸发。获得42.05克苯乙酸(3,4,4-三氟丁-3-烯基)酯,为清澈琥珀色液体。
元素分析: 计算值:C 59.02;H 4.54
实测值:C 59.29;H 4.60实施例26
将1.62克(0.01摩尔)羰基二咪唑(可由Aldrich获得)加入到于20毫升无水四氢呋喃(THF)中的1.89克(0.01摩尔)(L)-N-Boc-丙氨酸(可由Sigma获得)中,在室温下搅拌30分钟。之后加入1.5克(0.012摩尔)4-羟基-1,1,2-三氟丁-1-烯(参见,由US 5 389 680的合成实施例16),将混合物在室温下搅拌过夜。减压去除溶剂,残留物与水混合,用乙醚萃取。醚相用水洗涤(3次),经硫酸镁干燥。减压蒸发乙醚。获得2.25克N-叔丁氧基羰基-L-丙氨酸(3,4,4-三氟丁-3-烯基)酯,为清澈液体。
元素分析: 计算值:C 48.48;H 6.10;N 4.71
实测值:C 48.54;H 6.08;N 4.69实施例27
将过量的HCl气导入1.54克(0.0052摩尔)实施例26化合物的50毫升乙醚溶液中。之后将反应容器密封,将混合物在室温下搅拌6小时。将所得的无色沉淀物滤出,用乙醚洗涤,减压下干燥。获得0.8克L-丙氨酸(3,4,4-三氟丁-3-烯基)酯,为无色固体。
元素分析: 计算值:C 35.99;H 4.75;N 6.00;Cl15.18
实测值:C 36.00;H 4.71;N 5.96;Cl15.12
应用实施例实施例A临界浓度试验/线虫试验线虫:黄麻根结线虫溶剂: 4份重量的丙酮乳化剂:1份重量的烷基芳基聚乙二醇醚
生产活性化合物的适合制剂时,将1份重量的活性化合物与所述量的上述溶剂混合,并加入所述量的乳化剂,且所得的乳油用水稀释至所需浓度。
将活性化合物的制剂与土壤彻底混合,所述的土壤滋生大量的试验线虫。制剂中的活性化合物浓度不是关键的,只有每单位土壤体积的活性化合物量才是重要的,该量以ppm(=毫克/升)给出。将处理的土壤移至盆中,将莴苣播种于盆中,并将盆保持在25℃的温室中。
四周后,检查莴苣根的线虫(根结)感染情况,且确定活性化合物的效力,以%计。当完全避免感染时,效力为100%,当感染水平与未处理但同样感染的土壤中的对照植株一样高时,效力为0%。
在此试验中,在示范的20ppm活性化合物浓度下,例如制备实施例1和5的化合物显示出100%的效力。实施例B蝇幼虫的发育抑制作用试验试虫:铜绿蝇(Lucilia cuprina)(OP-抗性)所有的幼虫期
[蛹和成虫(不与活性物质接触)]溶剂: 35份重量的乙二醇单甲基醚乳化剂:35份重量的壬基苯酚聚乙二醇醚
生产适合的制剂时,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,且所得的乳油各用水稀释至所需浓度。
对于每一浓度液,将30至50只幼虫转移到置于玻璃试管中的马肉(1cm3)上,并向此马肉用吸管移500微升试验稀释液。将玻璃试管放入底部盖有一层海沙的塑料烧杯中,并保持在恒温箱(26℃±1.5℃,70%相对湿度±10%)中。24和48小时后检查活性(杀幼虫作用)。在幼虫出现后(大约72小时后),将试管移出,且在烧杯上盖上打了孔的塑料盖。在1.5倍于发育期(对照蝇羽化),计数羽化的蝇和蛹/围蛹数。
作用的标准是幼虫处理后48小时死亡(杀幼虫效果)或抑制由蛹羽化出成虫或抑制化蛹。物质的体外作用标准是抑制蝇的发育或将发育阻止在成虫期前。100%杀幼虫活性是指所有幼虫在48小时后被杀死。100%发育抑制活性是指没有羽化出成蝇。
在此试验中,在示范的1000ppm活性化合物浓度下,例如制备实施例1和5的化合物显示出100%的效力。实施例C微小牛蜱(SP-抗性Parkurst品系)抗性试验试虫:自己吸足血的雌成虫溶剂:二甲基亚砜
将20mg活性物质溶于1ml二甲基亚砜中,并用相同的溶剂稀释,制成低浓度液。
试验重复5次。将1微升溶液注射入腹部,并将试虫转移到培养皿中,保持在培养室中。由抑制产卵来确定活性。100%是指没有蜱产卵。
在此试验中,在示范的20微克/虫的活性化合物浓度下,例如制备实施例1和5的化合物显示出100%的效力。实施例D
此试验按照描述于US-5 389 680中的方法进行,该方法并入本文作为参考。
在线虫试验中(马铃薯和大豆),制备实施例26的化合物在方法1中在500ppm下具有95%的活性,在方法2中在1毫克/盆的浓度下具有2级活性,而在0.5克/盆和0.25克/盆的浓度下无活性,活性等级如US 5 389680中所定义,其中0级指活性达50%,1级指活性为50至75%,2级指活性为75至90%且3级指活性为91至100%。
Claims (10)
其中
R1 代表氢或卤素,
且Q代表或者
a)
其中 ,
R2 代表氢、硝基、氰基、卤素、烷基、烷氧基、烷硫基或任选取代的芳基且
R3 代表COOH、SO3H、NR4R5或OR6,其中
R4 代表氢、烷基或任选取代的芳基,
R5 代表氢、烷基、任选取代的芳基或COR7,
R6 代表氢、任选取代的芳烷基、CONR4R5或COR7,
R7 代表烷基、链烯基、任选取代的芳基或NR4R8,且
R8 代表氢、烷基或任选取代的芳基,或者
b)是ZR9或Z(P=W)R10R11,其中
Z 代表具有一至四个碳原子的脂族基团,其条件是,如果Z代表CH2,则R9不代表苯基,
W 代表氧或硫,
R9 α)代表芳族基团或代表杂环基基团(如选自吡唑基、咪唑基、三唑基、吗啉基、哌啶基、哌嗪基或吡咯烷基的环状基团),它们各任选由至少一个选自下列的取代基取代:氰基,三甲基甲硅烷基,羟基,烷基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团,
β)代表氢,OR12,SR12,卤素,NR12R13,氰基,三甲基甲硅烷基,硝基,苯基,磺酸或其酯、酰胺或硫酯的基团或代表脂族基团,该脂族基团任选由至少一个选自下列的基团取代:氰基,三甲基甲硅烷基,羟基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,苯基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团,
其中
R12和R13相互独立地各代表
i) 氢,
ii) 具有一至十二个碳原子的脂族基团或芳族或杂环基基团,它们
各任选由至少一个选自下列的基团取代:具有一至四个碳原子的烷
基,氰基,三甲基甲硅烷基,羟基,烷氧基,卤素,硝基,任选单
-或二烷基-取代的氨基,巯基,烷硫基,苯基,磺酸、磷酸、膦酸
或羧酸或上述酸之一的酯、酰胺或硫酯的基团,
iii) 或R12或R13与相连的氮原子一起形成氨基酸的一部分,或如果R12 代表氢,或脂族或芳族基团,它们各任选由至少一个选自下列的取代基取代:具有1至4个碳原子的烷基,羟基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团,或苯基,那么R13 还代表OR16、COR16、COOR21、NR16R17、SO2R18、
P(=O)R19R20,其中R16和R17相互独立地各代表氢、烷基或芳基,R18代表氢、烷基、卤代烷基或芳基,R19和R20相互独立地代表氢、烷基、芳基、烷基、烷硫基、芳硫基、烷基氨基、二烷基氨基、芳基氨基或OR21,且R21 代表氢、烷基或芳基,R10和R11相互独立地各代表R22、OR22、SR22或NR22R23,其中R22和R23相互独立地各代表氢,或脂族或芳族基团,它们各任选由至少一个选自下列的取代基取代:氰基,三甲基甲硅烷基,羟基,烷氧基,卤素,硝基,任选单-或二烷基-取代的氨基,巯基,烷硫基,苯基,磺酸、磷酸、膦酸或羧酸或上述酸之一的酯、酰胺或硫酯的基团。
2.根据权利要求1的式(I)化合物,具有结构式(Ia)、(Ib-1)或(Ib-2):CF2=CR1-CH2-CH2-O-CO-ZR9 (Ib-1)CF2=CR1-CH2-CH2-O-CO-Z(P=W)R10R11 (Ib-2)
其中R1、R2、R3、R9、R10、R11、Z和W各如权利要求1中所定义。
3.制备根据权利要求2的式(Ia)化合物的方法,其特征在于
其中
X(+)代表碱金属离子或铵离子,且
其中
R1 如权利要求1中所定义,
或者
B) 如果适宜在碱存在下,且如果适宜在稀释剂存在下,使式(IV)的靛红酸酐与式(V)的氟丁烯醇反应,
其中
R2、R3和R4各如权利要求1中所定义,
其中
R1如上定义,
或者
其中
Y代表CO或SO2,且
R2和R3各如权利要求1中所定义,
其中
R1如上所定义。
4.根据权利要求2的式(Ia)化合物,其中
R1代表氢、氟、氯或溴,
R2代表氢,硝基,氰基,氟,氯,溴,C1-C8-烷基,C1-C6-烷氧基,C1-C6-烷硫基,或任选氰基-、氟-、氯-、溴-或C1-C6-烷氧基-取代的苯基,
R3代表2-COOH、2-SO3H、NR4R5或OR6,
R4代表氢,C1-C8-烷基,或任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基,
R5代表氢,C1-C8-烷基,任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基或代表COR7,
R6代表氢,任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基-C1-C6-烷基或代表CONR4R5或COR7,
R7代表C1-C8-烷基,C2-C6-链烯基,任选氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基或代表NR4R8,
R8代表氢,C1-C8-烷基,或任选氰基-、氟-、氯-、溴-、C1-C6-烷基-或C1-C6-烷氧基-取代的苯基。
5.根据权利要求2的式(Ia)化合物,其中
R1代表氢或氟,
R2代表氢,硝基,氰基,氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,或任选氟-、氯-或C1-C4-烷氧基-取代的苯基,
R3代表2-COOH、2-SO3H、NR4R5或OR6,
R4代表氢,C1-C4-烷基,或任选氟-、氯-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基,
R5代表氢,C1-C4-烷基,任选氟-、氯-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基或代表COR7,
R6代表氢,任选氟-、氯-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基或代表CONR4R5或COR7,
R7代表C1-C4-烷基,C2-C6-链烯基,任选氟-、氯-或C1-C4-烷基-取代的苯基或代表NR4R8,
R8代表氢,C1-C4-烷基,或任选氟-、氯-、C1-C4-烷基-或C1-C4-烷氧基-取代的苯基。
6.杀虫剂,其特征在于,它们包含至少一种根据权利要求1的式(I)化合物。
7.根据权利要求1的式(I)化合物用于防治害虫的应用。
8.防治害虫的方法,其特征在于,使根据权利要求1的式(I)化合物作用于害虫和/或其栖息地。
9.制备农药的方法,其特征在于,将根据权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
10.根据权利要求1的式(I)化合物制备农药的应用。
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US327995P | 1995-08-25 | 1995-08-25 | |
DE1995131276 DE19531276A1 (de) | 1995-08-25 | 1995-08-25 | Arylester |
US60/003,279 | 1995-08-25 | ||
DE19531267.7 | 1995-08-25 |
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JP4409944B2 (ja) * | 2001-09-28 | 2010-02-03 | クミアイ化学工業株式会社 | ジフルオロアルケン誘導体、それを含有する有害生物防除剤及びその製造中間体 |
WO2003042153A1 (fr) * | 2001-11-15 | 2003-05-22 | Kumiai Chemical Industry Co., Ltd. | Derive de difluoroalcene, et pesticide renfermant ce derive |
AU2003252536A1 (en) * | 2002-08-01 | 2004-02-23 | Basf Aktiengesellschaft | Pesticidal fluoroalkene derivatives |
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