CN1863767A - 用于防治动物害虫的2-氰基苯磺酰胺 - Google Patents
用于防治动物害虫的2-氰基苯磺酰胺 Download PDFInfo
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- CN1863767A CN1863767A CNA2004800288418A CN200480028841A CN1863767A CN 1863767 A CN1863767 A CN 1863767A CN A2004800288418 A CNA2004800288418 A CN A2004800288418A CN 200480028841 A CN200480028841 A CN 200480028841A CN 1863767 A CN1863767 A CN 1863767A
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- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229960000521 lufenuron Drugs 0.000 description 1
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- OBWFJXLKRAFEDI-UHFFFAOYSA-N methyl cyanoformate Chemical group COC(=O)C#N OBWFJXLKRAFEDI-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000006099 n-pentyl sulfinyl group Chemical group 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229950001664 phoxim Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 238000006365 thiocyanation reaction Methods 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
Classifications
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
本发明涉及式(I)的2-氰基苯磺酰胺化合物和/或其可农用盐,其中变量R1-R5如权利要求1所定义。此外,本发明还涉及化合物(I)和/或其盐对抗动物害虫的用途;包含杀虫作用量的至少一种通式(I)化合物和/或至少一种I的可农用盐和至少一种惰性液体和/或固体农用载体以及需要的话至少一种表面活性剂的农用组合物;和一种对抗动物害虫的方法,包括使动物害虫,其栖息地,繁殖地,食物供应源,动物害虫生长或可能生长于其中的植物、种子、土壤、区域、材料或环境或需要防止动物侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种通式I的2-氰基苯磺酰胺化合物和/或至少一种其可农用盐接触。
Description
本发明涉及2-氰基苯磺酰胺化合物及其可农用盐以及包含这类化合物的组合物。本发明还涉及2-氰基苯磺酰胺化合物、其盐或包含它们的组合物在对抗动物害虫中的用途。
动物害虫破坏生长作物和收获的作物并且侵袭木质住宅和商业结构体,对食品供应和性能造成大的经济损失。尽管已知许多杀虫试剂,但由于目标害虫能够对所述试剂产生耐受性,因此仍然需要对抗动物害虫的新试剂。尤其难以有效防治诸如昆虫和螨虫的动物害虫。
EP 0033984描述了具有杀蚜虫活性的取代的2-氰基苯磺酰胺化合物。该苯磺酰胺化合物优选在苯基环的3位带有氟原子或氯原子。然而,所述化合物的杀虫活性并不令人满意且它们仅对蚜虫有活性。
因此,本发明的目的是提供尤其对难以防治的昆虫和螨虫具有良好杀虫活性的化合物。
已经发现这些目的由通式I的2-氰基苯磺酰胺化合物及其可农用盐实现:
其中
R1为C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R2为氢、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C8环烷基或C1-C4烷氧基,其中后提到的五个基团可以未被取代、部分或完全被卤代和/或可以带有1、2或3个选自C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4烷氧羰基、氰基、氨基、(C1-C4烷基)氨基、二(C1-C4烷基)氨基、C3-C8环烷基和苯基的基团,其中苯基可以未被取代、部分或完全被卤代和/或带有1、2或3个选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基的取代基;和
R3、R4和R5相互独立地选自氢、卤素、氰基、硝基、C1-C6烷基、C3-C8环烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷氧基,C1-C4卤代烷硫基、C2-C6链烯基、C2-C6炔基、C1-C4烷氧羰基、氨基、(C1-C4烷基)氨基、二(C1-C4烷基)氨基、氨基羰基、(C1-C4烷基)氨基羰基和二(C1-C4烷基)氨基羰基。
式I化合物及其可农用盐尤其对于难以防治的昆虫和螨虫具有高杀虫活性。
因此,本发明涉及通式I的2-氰基苯磺酰胺化合物及其可农用盐。
此外,本发明还涉及:
-化合物I和/或其盐在对抗动物害虫中的用途;
-农用组合物,包含杀虫作用量的至少一种式I的2-氰基苯磺酰胺化合物和/或至少一种I的可农用盐和至少一种惰性液体和/或固体可农用载体以及需要的话至少一种表面活性剂;和
-一种对抗动物害虫的方法,包括使动物害虫,其栖息地,繁殖地,食物供应源,动物害虫生长或可能生长于其中的植物、种子、土壤、区域、材料或环境或需要防止动物侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种通式I的2-氰基苯磺酰胺化合物和/或至少一种其可农用盐接触。
在取代基R1-R5中,通式I的化合物可以具有一个或多个手性中心,此时它们以对映体或非对映体的混合物存在。本发明提供了纯对映体或非对映体或其混合物。
适用于本发明的式I化合物的盐尤其是可农用盐。它们可以常规方法形成,例如通过使该化合物与所述阴离子的酸反应。
合适的可农用盐尤其是其阳离子和阴离子分别对本发明化合物的作用没有任何不利影响的那些阳离子的盐或那些酸的酸加成盐,这些盐可以用于抵抗有害昆虫或蜘蛛。因此,合适的阳离子尤其是碱金属离子,优选锂、钠和钾离子;碱土金属离子,优选钙、镁和钡离子;过渡金属离子,优选锰、铜、锌和铁离子;还有铵离子,需要的话其可以带有1-4个C1-C4烷基取代基和/或一个苯基或苄基取代基,优选二异丙基铵、四甲基铵、四丁基铵、三甲基苄基铵,此外还有鏻离子,锍离子,优选三(C1-C4烷基)锍和氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根和C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。它们可以通过使式Ia和Ib化合物与对应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
在各变量的上述定义中提到的有机结构部分象术语卤素一样是各所列基团成员的集合性术语。前缀Cn-Cm在每种情况下表示该基团中的可能碳原子数。
术语卤素在每种情况下表示氟、溴、氯或碘。
其他含义例如是:
本文所用术语“C1-C4烷基”以及烷基氨基和二烷基氨基的烷基部分指具有1-4个碳原子的饱和直链或支化烃基,即例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基或1,1-二甲基乙基。
本文所用术语“C1-C6烷基”指具有1-6个碳原子的饱和直链或支化烃基,例如在C1-C4烷基下提到的基团之一以及正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基。
本文所用术语“C1-C4卤代烷基”指如下具有1-4个碳原子的直链或支化饱和烷基(如上所述),其中这些基团中的一些或所有氢原子可以被氟、氯、溴和/或碘替代,即例如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基或九氟丁基。
本文所用术语“C1-C2氟烷基”指带有1、2、3、4或5个氟原子的C1-C2烷基,例如二氟甲基、三氟甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、1,1,2,2-四氟乙基或五氟乙基。
本文所用术语“C1-C4烷氧基”指具有1-4个碳原子的直链或支化饱和烷基(如上所述),其经由氧原子连接,即例如甲氧基、乙氧基、正丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基。
本文所用术语“C1-C4卤代烷氧基”指部分或完全被氟、氯、溴和/或碘取代的上述C1-C4烷氧基,即例如氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、2-氟乙氧基、2-氯乙氧基、2-溴乙氧基、2-碘乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、五氟乙氧基、2-氟丙氧基、3-氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、2-氯丙氧基、3-氯丙氧基、2,3-二氯丙氧基、2-溴丙氧基、3-溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氯丙氧基、2,2,3,3,3-五氟丙氧基、七氟丙氧基、1-(氟甲基)-2-氟乙氧基、1-(氯甲基)-2-氯乙氧基、1-(溴甲基)-2-溴乙氧基、4-氟丁氧基、4-氯丁氧基、4-溴丁氧基或九氟丁氧基。
本文所用术语“C1-C4烷硫基(C1-C4烷基硫基:C1-C4烷基-S-)”指具有1-4个碳原子的直链或支化饱和烷基(如上所述),其经由硫原子连接,即例如甲硫基、乙硫基、正丙硫基、1-甲基乙硫基、丁硫基、1-甲基丙硫基、2-甲基丙硫基或1,1-二甲基乙硫基。
本文所用术语“C1-C4烷基亚磺酰基”(C1-C4烷基-S(=O)-)指具有1-4个碳原子的直链或支化饱和烃基(如上所述),其通过在该烷基中的任何键处的亚磺酰基的硫原子键合,即例如SO-CH3、SO-C2H5、正丙基亚磺酰基、1-甲基乙基亚磺酰基、正丁基亚磺酰基、1-甲基丙基亚磺酰基、2-甲基丙基亚磺酰基、1,1-二甲基乙基亚磺酰基、正戊基亚磺酰基、1-甲基丁基亚磺酰基、2-甲基丁基亚磺酰基、3-甲基丁基亚磺酰基、1,1-二甲基丙基亚磺酰基、1,2-二甲基丙基亚磺酰基、2,2-二甲基丙基亚磺酰基或1-乙基丙基亚磺酰基。
本文所用术语“C1-C4烷基磺酰基”(C1-C4烷基-S(=O)2-)指具有1-4个碳原子的直链或支化饱和烷基(如上所述),其经由在该烷基的任何键处的磺酰基的硫原子键合,即例如SO2-CH3、SO2-C2H5、正丙基磺酰基、SO2-CH(CH3)2、正丁基磺酰基、1-甲基丙基磺酰基、2-甲基丙基磺酰基或SO2-C(CH3)3。
本文所用术语“C1-C4卤代烷硫基”指部分或完全被氟、氯、溴和/或碘取代的上述C1-C4烷硫基,即例如氟甲硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、溴二氟甲硫基、2-氟乙硫基、2-氯乙硫基、2-溴乙硫基、2-碘乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2,2,2-三氯乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、五氟乙硫基、2-氟丙硫基、3-氟丙硫基、2-氯丙硫基、3-氯丙硫基、2-溴丙硫基、3-溴丙硫基、2,2-二氟丙硫基、2,3-二氟丙硫基、2,3-二氯丙硫基、3,3,3-三氟丙硫基、3,3,3-三氯丙硫基、2,2,3,3,3-五氟丙硫基、七氟丙硫基、1-(氟甲基)-2-氟乙硫基、1-(氯甲基)-2-氯乙硫基、1-(溴甲基)-2-溴乙硫基、4-氟丁硫基、4-氯丁硫基、4-溴丁硫基或九氟丁硫基。
本文所用术语“C1-C4烷氧羰基”指具有1-4个碳原子的直链或支化烷氧基(如上所述),其经由羰基的碳原子连接,即例如甲氧羰基、乙氧羰基、正丙氧羰基、1-甲基乙氧羰基、正丁氧羰基、1-甲基丙氧羰基、2-甲基丙氧羰基或1,1-二甲基乙氧羰基。
本文所用的术语“(C1-C4烷基氨基)羰基”例如指甲基氨基羰基、乙基氨基羰基、丙基氨基羰基、1-甲基乙基氨基羰基、丁基氨基羰基、1-甲基丙基氨基羰基、2-甲基丙基氨基羰基或1,1-二甲基乙基氨基羰基。
本文所用的术语“二(C1-C4烷基)氨基羰基”指例如N,N-二甲基氨基羰基、N,N-二乙基氨基羰基、N,N-二(1-甲基乙基)氨基羰基、N,N-二丙基氨基羰基、N,N-二丁基氨基羰基、N,N-二(1-甲基丙基)氨基羰基、N,N-二(2-甲基丙基)氨基羰基、N,N-二(1,1-二甲基乙基)氨基羰基、N-乙基-N-甲基氨基羰基、N-甲基-N-丙基氨基羰基、N-甲基-N-(1-甲基乙基)氨基羰基、N-丁基-N-甲基氨基羰基、N-甲基-N-(1-甲基丙基)氨基羰基、N-甲基-N-(2-甲基丙基)氨基羰基、N-(1,1-二甲基乙基)-N-甲基氨基羰基、N-乙基-N-丙基氨基羰基、N-乙基-N-(1-甲基乙基)氨基羰基、N-丁基-N-乙基氨基羰基、N-乙基-N-(1-甲基丙基)氨基羰基、N-乙基-N-(2-甲基丙基)氨基羰基、N-乙基-N-(1,1-二甲基乙基)氨基羰基、N-(1-甲基乙基)-N-丙基氨基羰基、N-丁基-N-丙基氨基羰基、N-(1-甲基丙基)-N-丙基氨基羰基、N-(2-甲基丙基)-N-丙基氨基羰基、N-(1,1-二甲基乙基)-N-丙基氨基羰基、N-丁基-N-(1-甲基乙基)氨基羰基、N-(1-甲基乙基)-N-(1-甲基丙基)氨基羰基、N-(1-甲基乙基)-N-(2-甲基丙基)氨基羰基、N-(1,1-二甲基乙基)-N-(1-甲基乙基)氨基羰基、N-丁基-N-(1-甲基丙基)氨基羰基、N-丁基-N-(2-甲基丙基)氨基羰基、N-丁基-N-(1,1-二甲基乙基)氨基羰基、N-(1-甲基丙基)-N-(2-甲基丙基)氨基羰基、N-(1,1-二甲基乙基)-N-(1-甲基丙基)氨基羰基或N-(1,1-二甲基乙基)-N-(2-甲基丙基)氨基羰基。
本文所用术语“C2-C6链烯基”指具有2-6个碳原子和在任意位置的双键的直链或支化单不饱和烃基,即例如乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基。
本文所用术语“C2-C6炔基”指含有C-C叁键且具有2-6个碳原子的直链或支化脂族烃基,例如乙炔基、丙-1-炔-1-基、丙-2-炔-1-基、正丁-1-炔-1-基、正丁-1-炔-3-基、正丁-1-炔-4-基、正丁-2-炔-1-基、正戊-1-炔-1-基、正戊-1-炔-3-基、正戊-1-炔-4-基、正戊-1-炔-5-基、正戊-2-炔-1-基、正戊-2-炔-4-基、正戊-2-炔-5-基、3-甲基丁-1-炔-3-基、3-甲基丁-1-炔-4-基、正己-1-炔-1-基、正己-1-炔-3-基、正己-1-炔-4-基、正己-1-炔-5-基、正己-1-炔-6-基、正己-2-炔-1-基、正己-2-炔-4-基、正己-2-炔-5-基、正己-2-炔-6-基、正己-3-炔-1-基、正己-3-炔-2-基、3-甲基戊-1-炔-1-基、3-甲基戊-1-炔-3-基、3-甲基戊-1-炔-4-基、3-甲基戊-1-炔-5-基、4-甲基戊-1-炔-1-基、4-甲基戊-2-炔-4-基或4-甲基戊-2-炔-5-基等。
本文所用术语“C3-C8环烷基”指具有3-8个碳原子的单环烃基,例如环丙基、环丁基、环戊基、环己基、环庚基或环辛基。
在通式I的2-氰基苯磺酰胺化合物中,优选其中变量R1和R2相互独立地,但尤其是组合具有下列含义的那些:
R1为C1-C2烷基,尤其是甲基,或C1-C2烷氧基,尤其是甲氧基;
R2为氢或具有1-4个碳原子的线性、环状或支链烃基,例如C1-C4烷基,尤其是甲基、乙基、正丙基、1-甲基乙基,环丙基,C1-C4烷氧基-C1-C4烷基,尤其是2-甲氧基乙基,C1-C4烷硫基-C1-C4烷基,尤其是2-甲硫基乙基或C2-C4炔基,尤其是丙-2-炔-1-基(炔丙基)。最优选其中R2选自甲基、乙基、1-甲基乙基和丙-2-炔-1-基的化合物I。
还优选如下通式I的2-氰基苯磺酰胺化合物,其中R1为C1-C4卤代烷氧基,尤其是C1卤代烷氧基,特别是三氟甲氧基、二氟甲氧基或氯二氟甲氧基。在这些化合物中,R2具有上述含义,优选氢或具有1-4个碳原子的线性、环状或支链烃基,例如C1-C4烷基,尤其是甲基、乙基、正丙基、1-甲基乙基,环丙基,C1-C4烷氧基-C1-C4烷基,尤其是2-甲氧基乙基,C1-C4烷硫基-C1-C4烷基,尤其是2-甲硫基乙基或C2-C4炔基,尤其是丙-2-炔-1-基(炔丙基)。最优选其中R2选自甲基、乙基、1-甲基乙基和丙-2-炔-1-基的化合物I。
本发明的优选实施方案涉及如下通式I的2-氰基苯磺酰胺化合物,其中变量R1和R2具有上述含义,尤其是优选的含义且基团R3、R4或R5中的至少一个不为氢。优选基团R3、R4和R5中的一个或两个代表氢。在这些化合物中,优选其中R3不为氢且优选代表卤素,尤其是氯或氟且其他基团R4和R5为氢的那些。
本发明的另一优选实施方案涉及如下通式I的2-氰基苯磺酰胺化合物,其中变量R1和R2具有上述含义,尤其是优选含义且基团R3、R4和R5中的每一个代表氢。
本发明优选的式I化合物的实例包括在下表A1-A16中给出的那些化合物,其中R3、R4、R5如表中所定义且其中R1和R2的定义给于表A的行中:
表A1:其中R3、R4和R5各自为氢且R1和R2如表A中的一行所定义的式I化合物;
表A2:其中R3为氯,R4和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A3:其中R3为氟,R4和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A4:其中R3为溴,R4和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A5:其中R3为碘,R4和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A6:其中R3为CH3,R4和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A7:其中R4为氯,R3和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A8:其中R4为氟,R3和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A9:其中R4为溴,R3和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A10:其中R4为碘,R3和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A11:其中R4为CH3,R3和R5为氢且R1和R2如表A中的一行所定义的式I化合物;
表A12:其中R5为氯,R3和R4为氢且R1和R2如表A中的一行所定义的式I化合物;
表A13:其中R5为氟,R3和R4为氢且R1和R2如表A中的一行所定义的式I化合物;
表A14:其中R5为溴,R3和R4为氢且R1和R2如表A中的一行所定义的式I化合物;
表A15:其中R5为碘,R3和R4为氢且R1和R2如表A中的一行所定义的式I化合物;
表A16:其中R5为CH3,R3和R4为氢且R1和R2如表A中的一行所定义的式I化合物;
表A:
R1 | R2 | |
1. | CH3 | H |
2. | CH3 | CH3 |
3. | CH3 | CH3CH2- |
4. | CH3 | (CH3)2CH- |
5. | CH3 | CH3CH2CH2- |
6. | CH3 | n-C4H9 |
7. | CH3 | (CH3)3C- |
8. | CH3 | (CH3)2CH-CH2- |
9. | CH3 | n-C5H11 |
10. | CH3 | (CH3)2CH-CH2-CH2- |
11. | CH3 | (C2H5)2-CH- |
12. | CH3 | (CH3)3C-CH2- |
13. | CH3 | (CH3)3C-CH2-CH2- |
14. | CH3 | C2H5CH(CH3)-CH2- |
15. | CH3 | CH3-CH2-C(CH3)2- |
16. | CH3 | (CH3)2CH-CH(CH3)- |
17. | CH3 | (CH3)3C-CH(CH3)- |
18. | CH3 | (CH3)2CH-CH2-CH(CH3)- |
19. | CH3 | CH3-CH2-C(CH3)(C2H5)- |
20. | CH3 | CH3-CH2-CH2-C(CH3)2- |
21. | CH3 | C2H5-CH2-CH(CH3)-CH2- |
22. | CH3 | 环丙基 |
23. | CH3 | 环丙基-CH2- |
24. | CH3 | 环丙基-CH(CH3)- |
25. | CH3 | 环丁基 |
26. | CH3 | 环戊基 |
27. | CH3 | 环己基 |
28. | CH3 | HC≡C-CH2- |
29. | CH3 | HC≡C-CH(CH3)- |
30. | CH3 | HC≡C-C(CH3)2- |
31. | CH3 | HC≡C-C(CH3)(C2H5)- |
R1 | R2 | |
32. | CH3 | HC≡C-C(CH3)(C3H7)- |
33. | CH3 | CH2=CH-CH2- |
34. | CH3 | H2C=CH-CH(CH3)- |
35. | CH3 | H2C=CH-C(CH3)2- |
36. | CH3 | H2C=CH-C(C2H5)(CH3)- |
37. | CH3 | C6H5-CH2- |
38. | CH3 | 4-(CH3)3C-C6H4-CH2- |
39. | CH3 | C6H5-CH2- |
40. | CH3 | 4-(CH3)3C-C6H4-CH2- |
41. | CH3 | 4-Cl-C6H4-CH2- |
42. | CH3 | 3-(CH3O)-C6H4-CH2- |
43. | CH3 | 4-(CH3O)-C6H4-CH2- |
44. | CH3 | 2-(CH3O)-C6H4-CH2- |
45. | CH3 | 3-Cl-C6H4-CH2- |
46. | CH3 | 2-Cl-C6H4-CH2- |
47. | CH3 | 4-(F3C)-C6H4-CH2- |
48. | CH3 | NC-CH2- |
49. | CH3 | NC-CH2-CH2- |
50. | CH3 | NC-CH2-CH(CH3)- |
51. | CH3 | NC-CH2-C(CH3)2- |
52. | CH3 | NC-CH2-CH2-CH2- |
53. | CH3 | FH2C-CH2- |
54. | CH3 | ClH2C-CH2- |
55. | CH3 | BrH2C-CH2- |
56. | CH3 | FH2C-CH(CH3)- |
57. | CH3 | ClH2C-CH(CH3)- |
58. | CH3 | BrH2C-CH(CH3)- |
59. | CH3 | F2HC-CH2- |
60. | CH3 | F3C-CH2- |
61. | CH3 | FH2C-CH2-CH2- |
62. | CH3 | ClH2C-CH2-CH2- |
63. | CH3 | BrH2C-CH2-CH2- |
64. | CH3 | F2HC-CH2-CH2- |
R1 | R2 | |
65. | CH3 | F3C-CH2-CH2- |
66. | CH3 | CH3-O-CH2-CH2- |
67. | CH3 | CH3-S-CH2-CH2- |
68. | CH3 | CH3-SO2-CH2-CH2- |
69. | CH3 | C2H5-O-CH2-CH2- |
70. | CH3 | (CH3)2CH-O-CH2-CH2- |
71. | CH3 | C2H5-S-CH2-CH2- |
72. | CH3 | C2H5-SO2-CH2-CH2- |
73. | CH3 | (CH3)2N-CH2-CH2- |
74. | CH3 | (C2H5)2N-CH2-CH2- |
75. | CH3 | [(CH3)2CH]2N-CH2-CH2- |
76. | CH3 | CH3-O-CH2-CH(CH3)- |
77. | CH3 | CH3-S-CH2-CH(CH3)- |
78. | CH3 | CH3-SO2-CH2-CH(CH3)- |
79. | CH3 | C2H5-O-CH2-CH(CH3)- |
80. | CH3 | C2H5-S-CH2-CH(CH3)- |
81. | CH3 | C2H5-SO2-CH2-CH(CH3)- |
82. | CH3 | (CH3)2N-CH2-CH(CH3)- |
83. | CH3 | (C2H5)2N-CH2-CH(CH3)- |
84. | CH3 | [(CH3)2CH]2N-CH2-CH(CH3)- |
85. | CH3 | CH3-O-CH(CH3)-CH2- |
86. | CH3 | CH3-S-CH(CH3)-CH2- |
87. | CH3 | CH3-SO2-CH(CH3)-CH2- |
88. | CH3 | C2H5-O-CH(CH3)-CH2- |
89. | CH3 | C2H5-S-CH(CH3)-CH2- |
90. | CH3 | C2H5-SO2-CH(CH3)-CH2- |
91. | CH3 | (CH3)2N-CH(CH3)-CH2- |
92. | CH3 | (C2H5)2N-CH(CH3)-CH2- |
93. | CH3 | [(CH3)2CH]2N-CH(CH3)-CH2- |
94. | CH3 | CH3-O-CH2-CH2-CH2- |
95. | CH3 | CH3-S-CH2-CH2-CH2- |
96. | CH3 | CH3-SO2-CH2-CH2-CH2- |
97. | CH3 | C2H5-O-CH2-CH2-CH2- |
R1 | R2 | |
98. | CH3 | C2H5-S-CH2-CH2-CH2- |
99. | CH3 | C2H5-SO2-CH2-CH2-CH2- |
100. | CH3 | (CH3)2N-CH2-CH2-CH2- |
101. | CH3 | (C2H5)2N-CH2-CH2-CH2- |
102. | CH3 | CH3-O-CH2-C(CH3)2- |
103. | CH3 | CH3-S-CH2-C(CH3)2- |
104. | CH3 | CH3-SO2-CH2-C(CH3)2- |
105. | CH3 | C2H5-O-CH2-C(CH3)2- |
106. | CH3 | C2H5-S-CH2-C(CH3)2- |
107. | CH3 | C2H5-SO2-CH2-C(CH3)2- |
108. | CH3 | (CH3)2N-CH2-C(CH3)2- |
109. | CH3 | (C2H5)2N-CH2-C(CH3)2- |
110. | CH3 | [(CH3)2CH]2N-CH2-C(CH3)2- |
111. | CH3 | Cl-CH2-C≡C-CH2- |
112. | CH3 | CH3-O-C(O)-CH2 |
113. | CH3 | C2H5-O-C(O)-CH2 |
114. | CH3 | CH3-O-C(O)-CH(CH3)- |
115. | CH3 | C2H5-O-C(O)-CH(CH3)- |
116. | CH3 | (CH3O)2CH-CH2- |
117. | CH3 | (C2H5O)2CH-CH2- |
118. | C2H5 | H |
119. | C2H5 | CH3 |
120. | C2H5 | CH3CH2- |
121. | C2H5 | (CH3)2CH- |
122. | C2H5 | CH3CH2CH2- |
123. | C2H5 | n-C4H9 |
124. | C2H5 | (CH3)3C- |
125. | C2H5 | (CH3)2CH-CH2- |
126. | C2H5 | n-C5H11 |
127. | C2H5 | (CH3)2CH-CH2-CH2- |
128. | C2H5 | (C2H5)2-CH- |
129. | C2H5 | (CH3)3C-CH2- |
130. | C2H5 | (CH3)3C-CH2-CH2- |
R1 | R2 | |
131. | C2H5 | C2H5CH(CH3)-CH2- |
132. | C2H5 | CH3-CH2-C(CH3)2- |
133. | C2H5 | (CH3)2CH-CH(CH3)- |
134. | C2H5 | (CH3)3C-CH(CH3)- |
135. | C2H5 | (CH3)2CH-CH2-CH(CH3)- |
136. | C2H5 | CH3-CH2-C(CH3)(C2H5)- |
137. | C2H5 | CH3-CH2-CH2-C(CH3)2- |
138. | C2H5 | C2H5-CH2-CH(CH3)-CH2- |
139. | C2H5 | 环丙基 |
140. | C2H5 | 环丙基-CH2- |
141. | C2H5 | 环丙基-CH(CH3)- |
142. | C2H5 | 环丁基 |
143. | C2H5 | 环戊基 |
144. | C2H5 | 环己基 |
145. | C2H5 | HC≡C-CH2- |
146. | C2H5 | HC≡C-CH(CH3)- |
147. | C2H5 | HC≡C-C(CH3)2- |
148. | C2H5 | HC≡C-C(CH3)(C2H5)- |
149. | C2H5 | HC≡C-C(CH3)(C3H7)- |
150. | C2H5 | CH2=CH-CH2- |
151. | C2H5 | H2C=CH-CH(CH3)- |
152. | C2H5 | H2C=CH-C(CH3)2- |
153. | C2H5 | H2C=CH-C(C2H5)(CH3)- |
154. | C2H5 | C6H5-CH2- |
155. | C2H5 | 4-(CH3)3C-C6H4-CH2- |
156. | C2H5 | C6H5-CH2- |
157. | C2H5 | 4-(CH3)3C-C6H4-CH2- |
158. | C2H5 | 4-Cl-C6H4-CH2- |
159. | C2H5 | 3-(CH3O)-C6H4-CH2- |
160. | C2H5 | 4-(CH3O)-C6H4-CH2- |
161. | C2H5 | 2-(CH3O)-C6H4-CH2- |
162. | C2H5 | 3-Cl-C6H4-CH2- |
163. | C2H5 | 2-Cl-C6H4-CH2- |
R1 | R2 | |
164. | C2H5 | 4-(F3C)-C6H4-CH2- |
165. | C2H5 | NC-CH2- |
166. | C2H5 | NC-CH2-CH2- |
167. | C2H5 | NC-CH2-CH(CH3)- |
168. | C2H5 | NC-CH2-C(CH3)2- |
169. | C2H5 | NC-CH2-CH2-CH2- |
170. | C2H5 | FH2C-CH2- |
171. | C2H5 | ClH2C-CH2- |
172. | C2H5 | BrH2C-CH2- |
173. | C2H5 | FH2C-CH(CH3)- |
174. | C2H5 | ClH2C-CH(CH3)- |
175. | C2H5 | BrH2C-CH(CH3)- |
176. | C2H5 | F2HC-CH2- |
177. | C2H5 | F3C-CH2- |
178. | C2H5 | FH2C-CH2-CH2- |
179. | C2H5 | ClH2C-CH2-CH2- |
180. | C2H5 | BrH2C-CH2-CH2- |
181. | C2H5 | F2HC-CH2-CH2- |
182. | C2H5 | F3C-CH2-CH2- |
183. | C2H5 | CH3-O-CH2-CH2- |
184. | C2H5 | CH3-S-CH2-CH2- |
185. | C2H5 | CH3-SO2-CH2-CH2- |
186. | C2H5 | C2H5-O-CH2-CH2- |
187. | C2H5 | (CH3)2CH-O-CH2-CH2- |
188. | C2H5 | C2H5-S-CH2-CH2- |
189. | C2H5 | C2H5-SO2-CH2-CH2- |
190. | C2H5 | (CH3)2N-CH2-CH2- |
191. | C2H5 | (C2H5)2N-CH2-CH2- |
192. | C2H5 | [(CH3)2CH]2N-CH2-CH2- |
193. | C2H5 | CH3-O-CH2-CH(CH3)- |
194. | C2H5 | CH3-S-CH2-CH(CH3)- |
195. | C2H5 | CH3-SO2-CH2-CH(CH3)- |
196. | C2H5 | C2H5-O-CH2-CH(CH3)- |
R1 | R2 | |
197. | C2H5 | C2H5-S-CH2-CH(CH3)- |
198. | C2H5 | C2H5-SO2-CH2-CH(CH3)- |
199. | C2H5 | (CH3)2N-CH2-CH(CH3)- |
200. | C2H5 | (C2H5)2N-CH2-CH(CH3)- |
201. | C2H5 | [(CH3)2CH]2N-CH2-CH(CH3)- |
202. | C2H5 | CH3-O-CH(CH3)-CH2- |
203. | C2H5 | CH3-S-CH(CH3)-CH2- |
204. | C2H5 | CH3-SO2-CH(CH3)-CH2- |
205. | C2H5 | C2H5-O-CH(CH3)-CH2- |
206. | C2H5 | C2H5-S-CH(CH3)-CH2- |
207. | C2H5 | C2H5-SO2-CH(CH3)-CH2- |
208. | C2H5 | (CH3)2N-CH(CH3)-CH2- |
209. | C2H5 | (C2H5)2N-CH(CH3)-CH2- |
210. | C2H5 | [(CH3)2CH]2N-CH(CH3)-CH2- |
211. | C2H5 | CH3-O-CH2-CH2-CH2- |
212. | C2H5 | CH3-S-CH2-CH2-CH2- |
213. | C2H5 | CH3-SO2-CH2-CH2-CH2- |
214. | C2H5 | C2H5-O-CH2-CH2-CH2- |
215. | C2H5 | C2H5-S-CH2-CH2-CH2- |
216. | C2H5 | C2H5-SO2-CH2-CH2-CH2- |
217. | C2H5 | (CH3)2N-CH2-CH2-CH2- |
218. | C2H5 | (C2H5)2N-CH2-CH2-CH2- |
219. | C2H5 | CH3-O-CH2-C(CH3)2- |
220. | C2H5 | CH3-S-CH2-C(CH3)2- |
221. | C2H5 | CH3-SO2-CH2-C(CH3)2- |
222. | C2H5 | C2H5-O-CH2-C(CH3)2- |
223. | C2H5 | C2H5-S-CH2-C(CH3)2- |
224. | C2H5 | C2H5-SO2-CH2-C(CH3)2- |
225. | C2H5 | (CH3)2N-CH2-C(CH3)2- |
226. | C2H5 | (C2H5)2N-CH2-C(CH3)2- |
227. | C2H5 | [(CH3)2CH]2N-CH2-C(CH3)2- |
228. | C2H5 | Cl-CH2-C≡C-CH2- |
229. | C2H5 | CH3-O-C(O)-CH2 |
R1 | R2 | |
230. | C2H5 | C2H5-O-C(O)-CH2 |
231. | C2H5 | CH3-O-C(O)-CH(CH3)- |
232. | C2H5 | C2H5-O-C(O)-CH(CH3)- |
233. | C2H5 | (CH3O)2CH-CH2- |
234. | C2H5 | (C2H5O)2CH-CH2- |
235. | OCH3 | H |
236. | OCH3 | CH3 |
237. | OCH3 | CH3CH2- |
238. | OCH3 | (CH3)2CH- |
239. | OCH3 | CH3CH2CH2- |
240. | OCH3 | n-C4H9 |
241. | OCH3 | (CH3)3C- |
242. | OCH3 | (CH3)2CH-CH2- |
243. | OCH3 | n-C5H11 |
244. | OCH3 | (CH3)2CH-CH2-CH2- |
245. | OCH3 | (C2H5)2-CH- |
246. | OCH3 | (CH3)3C-CH2- |
247. | OCH3 | (CH3)3C-CH2-CH2- |
248. | OCH3 | C2H5CH(CH3)-CH2- |
249. | OCH3 | CH3-CH2-C(CH3)2- |
250. | OCH3 | (CH3)2CH-CH(CH3)- |
251. | OCH3 | (CH3)3C-CH(CH3)- |
252. | OCH3 | (CH3)2CH-CH2-CH(CH3)- |
253. | OCH3 | CH3-CH2-C(CH3)(C2H5)- |
254. | OCH3 | CH3-CH2-CH2-C(CH3)2- |
255. | OCH3 | C2H5-CH2-CH(CH3)-CH2- |
256. | OCH3 | 环丙基 |
257. | OCH3 | 环丙基-CH2- |
258. | OCH3 | 环丙基-CH(CH3)- |
259. | OCH3 | 环丁基 |
260. | OCH3 | 环戊基 |
261. | OCH3 | 环己基 |
262. | OCH3 | HC≡C-CH2- |
R1 | R2 | |
263. | OCH3 | HC≡C-CH(CH3)- |
264. | OCH3 | HC≡C-C(CH3)2- |
265. | OCH3 | HC≡C-C(CH3)(C2H5)- |
266. | OCH3 | HC≡C-C(CH3)(C3H7)- |
267. | OCH3 | CH2=CH-CH2- |
268. | OCH3 | H2C=CH-CH(CH3)- |
269. | OCH3 | H2C=CH-C(CH3)2- |
270. | OCH3 | H2C=CH-C(C2H5)(CH3)- |
271. | OCH3 | C6H5-CH2- |
272. | OCH3 | 4-(CH3)3C-C6H4-CH2- |
273. | OCH3 | C6H5-CH2- |
274. | OCH3 | 4-(CH3)3C-C6H4-CH2- |
275. | OCH3 | 4-Cl-C6H4-CH2- |
276. | OCH3 | 3-(CH3O)-C6H4-CH2- |
277. | OCH3 | 4-(CH3O)-C6H4-CH2- |
278. | OCH3 | 2-(CH3O)-C6H4-CH2- |
279. | OCH3 | 3-Cl-C6H4-CH2- |
280. | OCH3 | 2-Cl-C6H4-CH2- |
281. | OCH3 | 4-(F3C)-C6H4-CH2- |
282. | OCH3 | NC-CH2- |
283. | OCH3 | NC-CH2-CH2- |
284. | OCH3 | NC-CH2-CH(CH3)- |
285. | OCH3 | NC-CH2-C(CH3)2- |
286. | OCH3 | NC-CH2-CH2-CH2- |
287. | OCH3 | FH2C-CH2- |
288. | OCH3 | ClH2C-CH2- |
289. | OCH3 | BrH2C-CH2- |
290. | OCH3 | FH2C-CH(CH3)- |
291. | OCH3 | ClH2C-CH(CH3)- |
292. | OCH3 | BrH2C-CH(CH3)- |
293. | OCH3 | F2HC-CH2- |
294. | OCH3 | F3C-CH2- |
295. | OCH3 | FH2C-CH2-CH2- |
R1 | R2 | |
296. | OCH3 | ClH2C-CH2-CH2- |
297. | OCH3 | BrH2C-CH2-CH2- |
298. | OCH3 | F2HC-CH2-CH2- |
299. | OCH3 | F3C-CH2-CH2- |
300. | OCH3 | CH3-O-CH2-CH2- |
301. | OCH3 | CH3-S-CH2-CH2- |
302. | OCH3 | CH3-SO2-CH2-CH2- |
303. | OCH3 | C2H5-O-CH2-CH2- |
304. | OCH3 | (CH3)2CH-O-CH2-CH2- |
305. | OCH3 | C2H5-S-CH2-CH2- |
306. | OCH3 | C2H5-SO2-CH2-CH2- |
307. | OCH3 | (CH3)2N-CH2-CH2- |
308. | OCH3 | (C2H5)2N-CH2-CH2- |
309. | OCH3 | [(CH3)2CH]2N-CH2-CH2- |
310. | OCH3 | CH3-O-CH2-CH(CH3)- |
311. | OCH3 | CH3-S-CH2-CH(CH3)- |
312. | OCH3 | CH3-SO2-CH2-CH(CH3)- |
313. | OCH3 | C2H5-O-CH2-CH(CH3)- |
314. | OCH3 | C2H5-S-CH2-CH(CH3)- |
315. | OCH3 | C2H5-SO2-CH2-CH(CH3)- |
316. | OCH3 | (CH3)2N-CH2-CH(CH3)- |
317. | OCH3 | (C2H5)2N-CH2-CH(CH3)- |
318. | OCH3 | [(CH3)2CH]2N-CH2-CH(CH3)- |
319. | OCH3 | CH3-O-CH(CH3)-CH2- |
320. | OCH3 | CH3-S-CH(CH3)-CH2- |
321. | OCH3 | CH3-SO2-CH(CH3)-CH2- |
322. | OCH3 | C2H5-O-CH(CH3)-CH2- |
323. | OCH3 | C2H5-S-CH(CH3)-CH2- |
324. | OCH3 | C2H5-SO2-CH(CH3)-CH2- |
325. | OCH3 | (CH3)2N-CH(CH3)-CH2- |
326. | OCH3 | (C2H5)2N-CH(CH3)-CH2- |
327. | OCH3 | [(CH3)2CH]2N-CH(CH3)-CH2- |
328. | OCH3 | CH3-O-CH2-CH2-CH2- |
R1 | R2 | |
329. | OCH3 | CH3-S-CH2-CH2-CH2- |
330. | OCH3 | CH3-SO2-CH2-CH2-CH2- |
331. | OCH3 | C2H5-O-CH2-CH2-CH2- |
332. | OCH3 | C2H5-S-CH2-CH2-CH2- |
333. | OCH3 | C2H5-SO2-CH2-CH2-CH2- |
334. | OCH3 | (CH3)2N-CH2-CH2-CH2- |
335. | OCH3 | (C2H5)2N-CH2-CH2-CH2- |
336. | OCH3 | CH3-O-CH2-C(CH3)2- |
337. | OCH3 | CH3-S-CH2-C(CH3)2- |
338. | OCH3 | CH3-SO2-CH2-C(CH3)2- |
339. | OCH3 | C2H5-O-CH2-C(CH3)2- |
340. | OCH3 | C2H5-S-CH2-C(CH3)2- |
341. | OCH3 | C2H5-SO2-CH2-C(CH3)2- |
342. | OCH3 | (CH3)2N-CH2-C(CH3)2- |
343. | OCH3 | (C2H5)2N-CH2-C(CH3)2- |
344. | OCH3 | [(CH3)2CH]2N-CH2-C(CH3)2- |
345. | OCH3 | Cl-CH2-C≡C-CH2- |
346. | OCH3 | CH3-O-C(O)-CH2 |
347. | OCH3 | C2H5-O-C(O)-CH2 |
348. | OCH3 | CH3-O-C(O)-CH(CH3)- |
349. | OCH3 | C2H5-O-C(O)-CH(CH3)- |
350. | OCH3 | (CH3O)2CH-CH2- |
351. | OCH3 | (C2H5O)2CH-CH2- |
352. | OC2H5 | H |
353. | OC2H5 | CH3 |
354. | OC2H5 | CH3CH2- |
355. | OC2H5 | (CH3)2CH- |
356. | OC2H5 | CH3CH2CH2- |
357. | OC2H5 | n-C4H9 |
358. | OC2H5 | (CH3)3C- |
359. | OC2H5 | (CH3)2CH-CH2- |
360. | OC2H5 | n-C5H11 |
361. | OC2H5 | (CH3)2CH-CH2-CH2- |
R1 | R2 | |
362. | OC2H5 | (C2H5)2-CH- |
363. | OC2H5 | (CH3)3C-CH2- |
364. | OC2H5 | (CH3)3C-CH2-CH2- |
365. | OC2H5 | C2H5CH(CH3)-CH2- |
366. | OC2H5 | CH3-CH2-C(CH3)2- |
367. | OC2H5 | (CH3)2CH-CH(CH3)- |
368. | OC2H5 | (CH3)3C-CH(CH3)- |
369. | OC2H5 | (CH3)2CH-CH2-CH(CH3)- |
370. | OC2H5 | CH3-CH2-C(CH3)(C2H5)- |
371. | OC2H5 | CH3-CH2-CH2-C(CH3)2- |
372. | OC2H5 | C2H5-CH2-CH(CH3)-CH2- |
373. | OC2H5 | 环丙基 |
374. | OC2H5 | 环丙基-CH2- |
375. | OC2H5 | 环丙基-CH(CH3)- |
376. | OC2H5 | 环丁基 |
377. | OC2H5 | 环戊基 |
378. | OC2H5 | 环己基 |
379. | OC2H5 | HC≡C-CH2- |
380. | OC2H5 | HC≡C-CH(CH3)- |
381. | OC2H5 | HC≡C-C(CH3)2- |
382. | OC2H5 | HC≡C-C(CH3)(C2H5)- |
383. | OC2H5 | HC≡C-C(CH3)(C3H7)- |
384. | OC2H5 | CH2=CH-CH2- |
385. | OC2H5 | H2C=CH-CH(CH3)- |
386. | OC2H5 | H2C=CH-C(CH3)2- |
387. | OC2H5 | H2C=CH-C(C2H5)(CH3)- |
388. | OC2H5 | C6H5-CH2- |
389. | OC2H5 | 4-(CH3)3C-C6H4-CH2- |
390. | OC2H5 | C6H5-CH2- |
391. | OC2H5 | 4-(CH3)3C-C6H4-CH2- |
392. | OC2H5 | 4-Cl-C6H4-CH2- |
393. | OC2H5 | 3-(CH3O)-C6H4-CH2- |
394. | OC2H5 | 4-(CH3O)-C6H4-CH2- |
R1 | R2 | |
395. | OC2H5 | 2-(CH3O)-C6H4-CH2- |
396. | OC2H5 | 3-Cl-C6H4-CH2- |
397. | OC2H5 | 2-Cl-C6H4-CH2- |
398. | OC2H5 | 4-(F3C)-C6H4-CH2- |
399. | OC2H5 | NC-CH2- |
400. | OC2H5 | NC-CH2-CH2- |
401. | OC2H5 | NC-CH2-CH(CH3)- |
402. | OC2H5 | NC-CH2-C(CH3)2- |
403. | OC2H5 | NC-CH2-CH2-CH2- |
404. | OC2H5 | FH2C-CH2- |
405. | OC2H5 | ClH2C-CH2- |
406. | OC2H5 | BrH2C-CH2- |
407. | OC2H5 | FH2C-CH(CH3)- |
408. | OC2H5 | ClH2C-CH(CH3)- |
409. | OC2H5 | BrH2C-CH(CH3)- |
410. | OC2H5 | F2HC-CH2- |
411. | OC2H5 | F3C-CH2- |
412. | OC2H5 | FH2C-CH2-CH2- |
413. | OC2H5 | ClH2C-CH2-CH2- |
414. | OC2H5 | BrH2C-CH2-CH2- |
415. | OC2H5 | F2HC-CH2-CH2- |
416. | OC2H5 | F3C-CH2-CH2- |
417. | OC2H5 | CH3-O-CH2-CH2- |
418. | OC2H5 | CH3-S-CH2-CH2- |
419. | OC2H5 | CH3-SO2-CH2-CH2- |
420. | OC2H5 | C2H5-O-CH2-CH2- |
421. | OC2H5 | (CH3)2CH-O-CH2-CH2- |
422. | OC2H5 | C2H5-S-CH2-CH2- |
423. | OC2H5 | C2H5-SO2-CH2-CH2- |
424. | OC2H5 | (CH3)2N-CH2-CH2- |
425. | OC2H5 | (C2H5)2N-CH2-CH2- |
426. | OC2H5 | [(CH3)2CH]2N-CH2-CH2- |
427. | OC2H5 | CH3-O-CH2-CH(CH3)- |
R1 | R2 | |
428. | OC2H5 | CH3-S-CH2-CH(CH3)- |
429. | OC2H5 | CH3-SO2-CH2-CH(CH3)- |
430. | OC2H5 | C2H5-O-CH2-CH(CH3)- |
431. | OC2H5 | C2H5-S-CH2-CH(CH3)- |
432. | OC2H5 | C2H5-SO2-CH2-CH(CH3)- |
433. | OC2H5 | (CH3)2N-CH2-CH(CH3)- |
434. | OC2H5 | (C2H5)2N-CH2-CH(CH3)- |
435. | OC2H5 | [(CH3)2CH]2N-CH2-CH(CH3)- |
436. | OC2H5 | CH3-O-CH(CH3)-CH2- |
437. | OC2H5 | CH3-S-CH(CH3)-CH2- |
438. | OC2H5 | CH3-SO2-CH(CH3)-CH2- |
439. | OC2H5 | C2H5-O-CH(CH3)-CH2- |
440. | OC2H5 | C2H5-S-CH(CH3)-CH2- |
441. | OC2H5 | C2H5-SO2-CH(CH3)-CH2- |
442. | OC2H5 | (CH3)2N-CH(CH3)-CH2- |
443. | OC2H5 | (C2H5)2N-CH(CH3)-CH2- |
444. | OC2H5 | [(CH3)2CH]2N-CH(CH3)-CH2- |
445. | OC2H5 | CH3-O-CH2-CH2-CH2- |
446. | OC2H5 | CH3-S-CH2-CH2-CH2- |
447. | OC2H5 | CH3-SO2-CH2-CH2-CH2- |
448. | OC2H5 | C2H5-O-CH2-CH2-CH2- |
449. | OC2H5 | C2H5-S-CH2-CH2-CH2- |
450. | OC2H5 | C2H5-SO2-CH2-CH2-CH2- |
451. | OC2H5 | (CH3)2N-CH2-CH2-CH2- |
452. | OC2H5 | (C2H5)2N-CH2-CH2-CH2- |
453. | OC2H5 | CH3-O-CH2-C(CH3)2- |
454. | OC2H5 | CH3-S-CH2-C(CH3)2- |
455. | OC2H5 | CH3-SO2-CH2-C(CH3)2- |
456. | OC2H5 | C2H5-O-CH2-C(CH3)2- |
457. | OC2H5 | C2H5-S-CH2-C(CH3)2- |
458. | OC2H5 | C2H5-SO2-CH2-C(CH3)2- |
459. | OC2H5 | (CH3)2N-CH2-C(CH3)2- |
460. | OC2H5 | (C2H5)2N-CH2-C(CH3)2- |
R1 | R2 | |
461. | OC2H5 | [(CH3)2CH]2N-CH2-C(CH3)2- |
462. | OC2H5 | Cl-CH2-C≡C-CH2- |
463. | OC2H5 | CH3-O-C(O)-CH2 |
464. | OC2H5 | C2H5-O-C(O)-CH2 |
465. | OC2H5 | CH3-O-C(O)-CH(CH3)- |
466. | OC2H5 | C2H5-O-C(O)-CH(CH3)- |
467. | OC2H5 | (CH3O)2CH-CH2- |
468. | OC2H5 | (C2H5O)2CH-CH2- |
469. | CF3 | H |
470. | CF3 | CH3 |
471. | CF3 | CH3CH2- |
472. | CF3 | (CH3)2CH- |
473. | CF3 | CH3CH2CH2- |
474. | CF3 | n-C4H9 |
475. | CF3 | (CH3)3C- |
476. | CF3 | (CH3)2CH-CH2- |
477. | CF3 | n-C5H11 |
478. | CF3 | (CH3)2CH-CH2-CH2- |
479. | CF3 | (C2H5)2-CH- |
480. | CF3 | (CH3)3C-CH2- |
481. | CF3 | (CH3)3C-CH2-CH2- |
482. | CF3 | C2H5CH(CH3)-CH2- |
483. | CF3 | CH3-CH2-C(CH3)2- |
484. | CF3 | (CH3)2CH-CH(CH3)- |
485. | CF3 | (CH3)3C-CH(CH3)- |
486. | CF3 | (CH3)2CH-CH2-CH(CH3)- |
487. | CF3 | CH3-CH2-C(CH3)(C2H5)- |
488. | CF3 | CH3-CH2-CH2-C(CH3)2- |
489. | CF3 | C2H5-CH2-CH(CH3)-CH2- |
490. | CF3 | 环丙基 |
491. | CF3 | 环丙基-CH2- |
492. | CF3 | 环丙基-CH(CH3)- |
493. | CF3 | 环丁基 |
R1 | R2 | |
494. | CF3 | 环戊基 |
495. | CF3 | 环己基 |
496. | CF3 | HC≡C-CH2- |
497. | CF3 | HC≡C-CH(CH3)- |
498. | CF3 | HC≡C-C(CH3)2- |
499. | CF3 | HC≡C-C(CH3)(C2H5)- |
500. | CF3 | HC≡C-C(CH3)(C3H7)- |
501. | CF3 | CH2=CH-CH2- |
502. | CF3 | H2C=CH-CH(CH3)- |
503. | CF3 | H2C=CH-C(CH3)2- |
504. | CF3 | H2C=CH-C(C2H5)(CH3)- |
505. | CF3 | C6H5-CH2- |
506. | CF3 | 4-(CH3)3C-C6H4-CH2- |
507. | CF3 | C6H5-CH2- |
508. | CF3 | 4-(CH3)3C-C6H4-CH2- |
509. | CF3 | 4-Cl-C6H4-CH2- |
510. | CF3 | 3-(CH3O)-C6H4-CH2- |
511. | CF3 | 4-(CH3O)-C6H4-CH2- |
512. | CF3 | 2-(CH3O)-C6H4-CH2- |
513. | CF3 | 3-Cl-C6H4-CH2- |
514. | CF3 | 2-Cl-C6H4-CH2- |
515. | CF3 | 4-(F3C)-C6H4-CH2- |
516. | CF3 | NC-CH2- |
517. | CF3 | NC-CH2-CH2- |
518. | CF3 | NC-CH2-CH(CH3)- |
519. | CF3 | NC-CH2-C(CH3)2- |
520. | CF3 | NC-CH2-CH2-CH2- |
521. | CF3 | FH2C-CH2- |
522. | CF3 | ClH2C-CH2- |
523. | CF3 | BrH2C-CH2- |
524. | CF3 | FH2C-CH(CH3)- |
525. | CF3 | ClH2C-CH(CH3)- |
526. | CF3 | BrH2C-CH(CH3)- |
R1 | R2 | |
527. | CF3 | F2HC-CH2- |
528. | CF3 | F3C-CH2- |
529. | CF3 | FH2C-CH2-CH2- |
530. | CF3 | ClH2C-CH2-CH2- |
531. | CF3 | BrH2C-CH2-CH2- |
532. | CF3 | F2HC-CH2-CH2- |
533. | CF3 | F3C-CH2-CH2- |
534. | CF3 | CH3-O-CH2-CH2- |
535. | CF3 | CH3-S-CH2-CH2- |
536. | CF3 | CH3-SO2-CH2-CH2- |
537. | CF3 | C2H5-O-CH2-CH2- |
538. | CF3 | (CH3)2CH-O-CH2-CH2- |
539. | CF3 | C2H5-S-CH2-CH2- |
540. | CF3 | C2H5-SO2-CH2-CH2- |
541. | CF3 | (CH3)2N-CH2-CH2- |
542. | CF3 | (C2H5)2N-CH2-CH2- |
543. | CF3 | [(CH3)2CH]2N-CH2-CH2- |
544. | CF3 | CH3-O-CH2-CH(CH3)- |
545. | CF3 | CH3-S-CH2-CH(CH3)- |
546. | CF3 | CH3-SO2-CH2-CH(CH3)- |
547. | CF3 | C2H5-O-CH2-CH(CH3)- |
548. | CF3 | C2H5-S-CH2-CH(CH3)- |
549. | CF3 | C2H5-SO2-CH2-CH(CH3)- |
550. | CF3 | (CH3)2N-CH2-CH(CH3)- |
551. | CF3 | (C2H5)2N-CH2-CH(CH3)- |
552. | CF3 | [(CH3)2CH]2N-CH2-CH(CH3)- |
553. | CF3 | CH3-O-CH(CH3)-CH2- |
554. | CF3 | CH3-S-CH(CH3)-CH2- |
555. | CF3 | CH3-SO2-CH(CH3)-CH2- |
556. | CF3 | C2H5-O-CH(CH3)-CH2- |
557. | CF3 | C2H5-S-CH(CH3)-CH2- |
558. | CF3 | C2H5-SO2-CH(CH3)-CH2- |
559. | CF3 | (CH3)2N-CH(CH3)-CH2- |
R1 | R2 | |
560. | CF3 | (C2H5)2N-CH(CH3)-CH2- |
561. | CF3 | [(CH3)2CH]2N-CH(CH3)-CH2- |
562. | CF3 | CH3-O-CH2-CH2-CH2- |
563. | CF3 | CH3-S-CH2-CH2-CH2- |
564. | CF3 | CH3-SO2-CH2-CH2-CH2- |
565. | CF3 | C2H5-O-CH2-CH2-CH2- |
566. | CF3 | C2H5-S-CH2-CH2-CH2- |
567. | CF3 | C2H5-SO2-CH2-CH2-CH2- |
568. | CF3 | (CH3)2N-CH2-CH2-CH2- |
569. | CF3 | (C2H5)2N-CH2-CH2-CH2- |
570. | CF3 | CH3-O-CH2-C(CH3)2- |
571. | CF3 | CH3-S-CH2-C(CH3)2- |
572. | CF3 | CH3-SO2-CH2-C(CH3)2- |
573. | CF3 | C2H5-O-CH2-C(CH3)2- |
574. | CF3 | C2H5-S-CH2-C(CH3)2- |
575. | CF3 | C2H5-SO2-CH2-C(CH3)2- |
576. | CF3 | (CH3)2N-CH2-C(CH3)2- |
577. | CF3 | (C2H5)2N-CH2-C(CH3)2- |
578. | CF3 | [(CH3)2CH]2N-CH2-C(CH3)2- |
579. | CF3 | Cl-CH2-C≡C-CH2- |
580. | CF3 | CH3-O-C(O)-CH2 |
581. | CF3 | C2H5-O-C(O)-CH2 |
582. | CF3 | CH3-O-C(O)-CH(CH3)- |
583. | CF3 | C2H5-O-C(O)-CH(CH3)- |
584. | CF3 | (CH3O)2CH-CH2- |
585. | CF3 | (C2H5O)2CH-CH2- |
586. | OCHF2 | H |
587. | OCHF2 | CH3 |
588. | OCHF2 | CH3CH2- |
589. | OCHF2 | (CH3)2CH- |
590. | OCHF2 | CH3CH2CH2- |
591. | OCHF2 | n-C4H9 |
592. | OCHF2 | (CH3)3C- |
R1 | R2 | |
593. | OCHF2 | (CH3)2CH-CH2- |
594. | OCHF2 | n-C5H11 |
595. | OCHF2 | (CH3)2CH-CH2-CH2- |
596. | OCHF2 | (C2H5)2-CH- |
597. | OCHF2 | (CH3)3C-CH2- |
598. | OCHF2 | (CH3)3C-CH2-CH2- |
599. | OCHF2 | C2H5CH(CH3)-CH2- |
600. | OCHF2 | CH3-CH2-C(CH3)2- |
601. | OCHF2 | (CH3)2CH-CH(CH3)- |
602. | OCHF2 | (CH3)3C-CH(CH3)- |
603. | OCHF2 | (CH3)2CH-CH2-CH(CH3)- |
604. | OCHF2 | CH3-CH2-C(CH3)(C2H5)- |
605. | OCHF2 | CH3-CH2-CH2-C(CH3)2- |
606. | OCHF2 | C2H5-CH2-CH(CH3)-CH2- |
607. | OCHF2 | 环丙基 |
608. | OCHF2 | 环丙基-CH2- |
609. | OCHF2 | 环丙基-CH(CH3)- |
610. | OCHF2 | 环丁基 |
611. | OCHF2 | 环戊基 |
612. | OCHF2 | 环己基 |
613. | OCHF2 | HC≡C-CH2- |
614. | OCHF2 | HC≡C-CH(CH3)- |
615. | OCHF2 | HC≡C-C(CH3)2- |
616. | OCHF2 | HC≡C-C(CH3)(C2H5)- |
617. | OCHF2 | HC≡C-C(CH3)(C3H7)- |
618. | OCHF2 | CH2=CH-CH2- |
619. | OCHF2 | H2C=CH-CH(CH3)- |
620. | OCHF2 | H2C=CH-C(CH3)2- |
621. | OCHF2 | H2C=CH-C(C2H5)(CH3)- |
622. | OCHF2 | C6H5-CH2- |
623. | OCHF2 | 4-(CH3)3C-C6H4-CH2- |
624. | OCHF2 | C6H5-CH2- |
625. | OCHF2 | 4-(CH3)3C-C6H4-CH2- |
R1 | R2 | |
626. | OCHF2 | 4-Cl-C6H4-CH2- |
627. | OCHF2 | 3-(CH3O)-C6H4-CH2- |
628. | OCHF2 | 4-(CH3O)-C6H4-CH2- |
629. | OCHF2 | 2-(CH3O)-C6H4-CH2- |
630. | OCHF2 | 3-Cl-C6H4-CH2- |
631. | OCHF2 | 2-Cl-C6H4-CH2- |
632. | OCHF2 | 4-(F3C)-C6H4-CH2- |
633. | OCHF2 | NC-CH2- |
634. | OCHF2 | NC-CH2-CH2- |
635. | OCHF2 | NC-CH2-CH(CH3)- |
636. | OCHF2 | NC-CH2-C(CH3)2- |
637. | OCHF2 | NC-CH2-CH2-CH2- |
638. | OCHF2 | FH2C-CH2- |
639. | OCHF2 | ClH2C-CH2- |
640. | OCHF2 | BrH2C-CH2- |
641. | OCHF2 | FH2C-CH(CH3)- |
642. | OCHF2 | ClH2C-CH(CH3)- |
643. | OCHF2 | BrH2C-CH(CH3)- |
644. | OCHF2 | F2HC-CH2- |
645. | OCHF2 | F3C-CH2- |
646. | OCHF2 | FH2C-CH2-CH2- |
647. | OCHF2 | ClH2C-CH2-CH2- |
648. | OCHF2 | BrH2C-CH2-CH2- |
649. | OCHF2 | F2HC-CH2-CH2- |
650. | OCHF2 | F3C-CH2-CH2- |
651. | OCHF2 | CH3-O-CH2-CH2- |
652. | OCHF2 | CH3-S-CH2-CH2- |
653. | OCHF2 | CH3-SO2-CH2-CH2- |
654. | OCHF2 | C2H5-O-CH2-CH2- |
655. | OCHF2 | (CH3)2CH-O-CH2-CH2- |
656. | OCHF2 | C2H5-S-CH2-CH2- |
657. | OCHF2 | C2H5-SO2-CH2-CH2- |
658. | OCHF2 | (CH3)2N-CH2-CH2- |
R1 | R2 | |
659. | OCHF2 | (C2H5)2N-CH2-CH2- |
660. | OCHF2 | [(CH3)2CH]2N-CH2-CH2- |
661. | OCHF2 | CH3-O-CH2-CH(CH3)- |
662. | OCHF2 | CH3-S-CH2-CH(CH3)- |
663. | OCHF2 | CH3-SO2-CH2-CH(CH3)- |
664. | OCHF2 | C2H5-O-CH2-CH(CH3)- |
665. | OCHF2 | C2H5-S-CH2-CH(CH3)- |
666. | OCHF2 | C2H5-SO2-CH2-CH(CH3)- |
667. | OCHF2 | (CH3)2N-CH2-CH(CH3)- |
668. | OCHF2 | (C2H5)2N-CH2-CH(CH3)- |
669. | OCHF2 | [(CH3)2CH]2N-CH2-CH(CH3)- |
670. | OCHF2 | CH3-O-CH(CH3)-CH2- |
671. | OCHF2 | CH3-S-CH(CH3)-CH2- |
672. | OCHF2 | CH3-SO2-CH(CH3)-CH2- |
673. | OCHF2 | C2H5-O-CH(CH3)-CH2- |
674. | OCHF2 | C2H5-S-CH(CH3)-CH2- |
675. | OCHF2 | C2H5-SO2-CH(CH3)-CH2- |
676. | OCHF2 | (CH3)2N-CH(CH3)-CH2- |
677. | OCHF2 | (C2H5)2N-CH(CH3)-CH2- |
678. | OCHF2 | [(CH3)2CH]2N-CH(CH3)-CH2- |
679. | OCHF2 | CH3-O-CH2-CH2-CH2- |
680. | OCHF2 | CH3-S-CH2-CH2-CH2- |
681. | OCHF2 | CH3-SO2-CH2-CH2-CH2- |
682. | OCHF2 | C2H5-O-CH2-CH2-CH2- |
683. | OCHF2 | C2H5-S-CH2-CH2-CH2- |
684. | OCHF2 | C2H5-SO2-CH2-CH2-CH2- |
685. | OCHF2 | (CH3)2N-CH2-CH2-CH2- |
686. | OCHF2 | (C2H5)2N-CH2-CH2-CH2- |
687. | OCHF2 | CH3-O-CH2-C(CH3)2- |
688. | OCHF2 | CH3-S-CH2-C(CH3)2- |
689. | OCHF2 | CH3-SO2-CH2-C(CH3)2- |
690. | OCHF2 | C2H5-O-CH2-C(CH3)2- |
691. | OCHF2 | C2H5-S-CH2-C(CH3)2- |
R1 | R2 | |
692. | OCHF2 | C2H5-SO2-CH2-C(CH3)2- |
693. | OCHF2 | (CH3)2N-CH2-C(CH3)2- |
694. | OCHF2 | (C2H5)2N-CH2-C(CH3)2- |
695. | OCHF2 | [(CH3)2CH]2N-CH2-C(CH3)2- |
696. | OCHF2 | Cl-CH2-C≡C-CH2- |
697. | OCHF2 | CH3-O-C(O)-CH2 |
698. | OCHF2 | C2H5-O-C(O)-CH2 |
699. | OCHF2 | CH3-O-C(O)-CH(CH3)- |
700. | OCHF2 | C2H5-O-C(O)-CH(CH3)- |
701. | OCHF2 | (CH3O)2CH-CH2- |
702. | OCHF2 | (C2H5O)2CH-CH2- |
703. | OCF3 | H |
704. | OCF3 | CH3 |
705. | OCF3 | CH3CH2- |
706. | OCF3 | (CH3)2CH- |
707. | OCF3 | CH3CH2CH2- |
708. | OCF3 | n-C4H9 |
709. | OCF3 | (CH3)3C- |
710. | OCF3 | (CH3)2CH-CH2- |
711. | OCF3 | n-C5H11 |
712. | OCF3 | (CH3)2CH-CH2-CH2- |
713. | OCF3 | (C2H5)2-CH- |
714. | OCF3 | (CH3)3C-CH2- |
715. | OCF3 | (CH3)3C-CH2-CH2- |
716. | OCF3 | C2H5CH(CH3)-CH2- |
717. | OCF3 | CH3-CH2-C(CH3)2- |
718. | OCF3 | (CH3)2CH-CH(CH3)- |
719. | OCF3 | (CH3)3C-CH(CH3)- |
720. | OCF3 | (CH3)2CH-CH2-CH(CH3)- |
721. | OCF3 | CH3-CH2-C(CH3)(C2H5)- |
722. | OCF3 | CH3-CH2-CH2-C(CH3)2- |
723. | OCF3 | C2H5-CH2-CH(CH3)-CH2- |
724. | OCF3 | 环丙基 |
R1 | R2 | |
725. | OCF3 | 环丙基-CH2- |
726. | OCF3 | 环丙基-CH(CH3)- |
727. | OCF3 | 环丁基 |
728. | OCF3 | 环戊基 |
729. | OCF3 | 环己基 |
730. | OCF3 | HC≡C-CH2- |
731. | OCF3 | HC≡C-CH(CH3)- |
732. | OCF3 | HC≡C-C(CH3)2- |
733. | OCF3 | HC≡C-C(CH3)(C2H5)- |
734. | OCF3 | HC≡C-C(CH3)(C3H7)- |
735. | OCF3 | CH2=CH-CH2- |
736. | OCF3 | H2C=CH-CH(CH3)- |
737. | OCF3 | H2C=CH-C(CH3)2- |
738. | OCF3 | H2C=CH-C(C2H5)(CH3)- |
739. | OCF3 | C6H5-CH2- |
740. | OCF3 | 4-(CH3)3C-C6H4-CH2- |
741. | OCF3 | C6H5-CH2- |
742. | OCF3 | 4-(CH3)3C-C6H4-CH2- |
743. | OCF3 | 4-Cl-C6H4-CH2- |
744. | OCF3 | 3-(CH3O)-C6H4-CH2- |
745. | OCF3 | 4-(CH3O)-C6H4-CH2- |
746. | OCF3 | 2-(CH3O)-C6H4-CH2- |
747. | OCF3 | 3-Cl-C6H4-CH2- |
748. | OCF3 | 2-Cl-C6H4-CH2- |
749. | OCF3 | 4-(F3C)-C6H4-CH2- |
750. | OCF3 | NC-CH2- |
751. | OCF3 | NC-CH2-CH2- |
752. | OCF3 | NC-CH2-CH(CH3)- |
753. | OCF3 | NC-CH2-C(CH3)2- |
754. | OCF3 | NC-CH2-CH2-CH2- |
755. | OCF3 | FH2C-CH2- |
756. | OCF3 | ClH2C-CH2- |
757. | OCF3 | BrH2C-CH2- |
R1 | R2 | |
758. | OCF3 | FH2C-CH(CH3)- |
759. | OCF3 | ClH2C-CH(CH3)- |
760. | OCF3 | BrH2C-CH(CH3)- |
761. | OCF3 | F2HC-CH2- |
762. | OCF3 | F3C-CH2- |
763. | OCF3 | FH2C-CH2-CH2- |
764. | OCF3 | ClH2C-CH2-CH2- |
765. | OCF3 | BrH2C-CH2-CH2- |
766. | OCF3 | F2HC-CH2-CH2- |
767. | OCF3 | F3C-CH2-CH2- |
768. | OCF3 | CH3-O-CH2-CH2- |
769. | OCF3 | CH3-S-CH2-CH2- |
770. | OCF3 | CH3-SO2-CH2-CH2- |
771. | OCF3 | C2H5-O-CH2-CH2- |
772. | OCF3 | (CH3)2CH-O-CH2-CH2- |
773. | OCF3 | C2H5-S-CH2-CH2- |
774. | OCF3 | C2H5-SO2-CH2-CH2- |
775. | OCF3 | (CH3)2N-CH2-CH2- |
776. | OCF3 | (C2H5)2N-CH2-CH2- |
777. | OCF3 | [(CH3)2CH]2N-CH2-CH2- |
778. | OCF3 | CH3-O-CH2-CH(CH3)- |
779. | OCF3 | CH3-S-CH2-CH(CH3)- |
780. | OCF3 | CH3-SO2-CH2-CH(CH3)- |
781. | OCF3 | C2H5-O-CH2-CH(CH3)- |
782. | OCF3 | C2H5-S-CH2-CH(CH3)- |
783. | OCF3 | C2H5-SO2-CH2-CH(CH3)- |
784. | OCF3 | (CH3)2N-CH2-CH(CH3)- |
785. | OCF3 | (C2H5)2N-CH2-CH(CH3)- |
786. | OCF3 | [(CH3)2CH]2N-CH2-CH(CH3)- |
787. | OCF3 | CH3-O-CH(CH3)-CH2- |
788. | OCF3 | CH3-S-CH(CH3)-CH2- |
789. | OCF3 | CH3-SO2-CH(CH3)-CH2- |
790. | OCF3 | C2H5-O-CH(CH3)-CH2- |
R1 | R2 | |
791. | OCF3 | C2H5-S-CH(CH3)-CH2- |
792. | OCF3 | C2H5-SO2-CH(CH3)-CH2- |
793. | OCF3 | (CH3)2N-CH(CH3)-CH2- |
794. | OCF3 | (C2H5)2N-CH(CH3)-CH2- |
795. | OCF3 | [(CH3)2CH]2N-CH(CH3)-CH2- |
796. | OCF3 | CH3-O-CH2-CH2-CH2- |
797. | OCF3 | CH3-S-CH2-CH2-CH2- |
798. | OCF3 | CH3-SO2-CH2-CH2-CH2- |
799. | OCF3 | C2H5-O-CH2-CH2-CH2- |
800. | OCF3 | C2H5-S-CH2-CH2-CH2- |
801. | OCF3 | C2H5-SO2-CH2-CH2-CH2- |
802. | OCF3 | (CH3)2N-CH2-CH2-CH2- |
803. | OCF3 | (C2H5)2N-CH2-CH2-CH2- |
804. | OCF3 | CH3-O-CH2-C(CH3)2- |
805. | OCF3 | CH3-S-CH2-C(CH3)2- |
806. | OCF3 | CH3-SO2-CH2-C(CH3)2- |
807. | OCF3 | C2H5-O-CH2-C(CH3)2- |
808. | OCF3 | C2H5-S-CH2-C(CH3)2- |
809. | OCF3 | C2H5-SO2-CH2-C(CH3)2- |
810. | OCF3 | (CH3)2N-CH2-C(CH3)2- |
811. | OCF3 | (C2H5)2N-CH2-C(CH3)2- |
812. | OCF3 | [(CH3)2CH]2N-CH2-C(CH3)2- |
813. | OCF3 | Cl-CH2-C≡C-CH2- |
814. | OCF3 | CH3-O-C(O)-CH2 |
815. | OCF3 | C2H5-O-C(O)-CH2 |
816. | OCF3 | CH3-O-C(O)-CH(CH3)- |
817. | OCF3 | C2H5-O-C(O)-CH(CH3)- |
818. | OCF3 | (CH3O)2CH-CH2- |
819. | OCF3 | (C2H5O)2CH-CH2- |
820. | OCClF2 | H |
821. | OCClF2 | CH3 |
822. | OCClF2 | CH3CH2- |
823. | OCClF2 | (CH3)2CH- |
R1 | R2 | |
824. | OCClF2 | CH3CH2CH2- |
825. | OCClF2 | n-C4H9 |
826. | OCClF2 | (CH3)3C- |
827. | OCClF2 | (CH3)2CH-CH2- |
828. | OCClF2 | n-C5H11 |
829. | OCClF2 | (CH3)2CH-CH2-CH2- |
830. | OCClF2 | (C2H5)2-CH- |
831. | OCClF2 | (CH3)3C-CH2- |
832. | OCClF2 | (CH3)3C-CH2-CH2- |
833. | OCClF2 | C2H5CH(CH3)-CH2- |
834. | OCClF2 | CH3-CH2-C(CH3)2- |
835. | OCClF2 | (CH3)2CH-CH(CH3)- |
836. | OCClF2 | (CH3)3C-CH(CH3)- |
837. | OCClF2 | (CH3)2CH-CH2-CH(CH3)- |
838. | OCClF2 | CH3-CH2-C(CH3)(C2H5)- |
839. | OCClF2 | CH3-CH2-CH2-C(CH3)2- |
840. | OCClF2 | C2H5-CH2-CH(CH3)-CH2- |
841. | OCClF2 | 环丙基 |
842. | OCClF2 | 环丙基-CH2- |
843. | OCClF2 | 环丙基-CH(CH3)- |
844. | OCClF2 | 环丁基 |
845. | OCClF2 | 环戊基 |
846. | OCClF2 | 环己基 |
847. | OCClF2 | HC≡C-CH2- |
848. | OCClF2 | HC≡C-CH(CH3)- |
849. | OCClF2 | HC≡C-C(CH3)2- |
850. | OCClF2 | HC≡C-C(CH3)(C2H5)- |
851. | OCClF2 | HC≡C-C(CH3)(C3H7)- |
852. | OCClF2 | CH2=CH-CH2- |
853. | OCClF2 | H2C=CH-CH(CH3)- |
854. | OCClF2 | H2C=CH-C(CH3)2- |
855. | OCClF2 | H2C=CH-C(C2H5)(CH3)- |
856. | OCClF2 | C6H5-CH2- |
R1 | R2 | |
857. | OCClF2 | 4-(CH3)3C-C6H4-CH2- |
858. | OCClF2 | C6H5-CH2- |
859. | OCClF2 | 4-(CH3)3C-C6H4-CH2- |
860. | OCClF2 | 4-Cl-C6H4-CH2- |
861. | OCClF2 | 3-(CH3O)-C6H4-CH2- |
862. | OCClF2 | 4-(CH3O)-C6H4-CH2- |
863. | OCClF2 | 2-(CH3O)-C6H4-CH2- |
864. | OCClF2 | 3-Cl-C6H4-CH2- |
865. | OCClF2 | 2-Cl-C6H4-CH2- |
866. | OCClF2 | 4-(F3C)-C6H4-CH2- |
867. | OCClF2 | NC-CH2- |
868. | OCClF2 | NC-CH2-CH2- |
869. | OCClF2 | NC-CH2-CH(CH3)- |
870. | OCClF2 | NC-CH2-C(CH3)2- |
871. | OCClF2 | NC-CH2-CH2-CH2- |
872. | OCClF2 | FH2C-CH2- |
873. | OCClF2 | ClH2C-CH2- |
874. | OCClF2 | BrH2C-CH2- |
875. | OCClF2 | FH2C-CH(CH3)- |
876. | OCClF2 | ClH2C-CH(CH3)- |
877. | OCClF2 | BrH2C-CH(CH3)- |
878. | OCClF2 | F2HC-CH2- |
879. | OCClF2 | F3C-CH2- |
880. | OCClF2 | FH2C-CH2-CH2- |
881. | OCClF2 | ClH2C-CH2-CH2- |
882. | OCClF2 | BrH2C-CH2-CH2- |
883. | OCClF2 | F2HC-CH2-CH2- |
884. | OCClF2 | F3C-CH2-CH2- |
885. | OCClF2 | CH3-O-CH2-CH2- |
886. | OCClF2 | CH3-S-CH2-CH2- |
887. | OCClF2 | CH3-SO2-CH2-CH2- |
888. | OCClF2 | C2H5-O-CH2-CH2- |
889. | OCClF2 | (CH3)2CH-O-CH2-CH2- |
R1 | R2 | |
890. | OCClF2 | C2H5-S-CH2-CH2- |
891. | OCClF2 | C2H5-SO2-CH2-CH2- |
892. | OCClF2 | (CH3)2N-CH2-CH2- |
893. | OCClF2 | (C2H5)2N-CH2-CH2- |
894. | OCClF2 | [(CH3)2CH]2N-CH2-CH2- |
895. | OCClF2 | CH3-O-CH2-CH(CH3)- |
896. | OCClF2 | CH3-S-CH2-CH(CH3)- |
897. | OCClF2 | CH3-SO2-CH2-CH(CH3)- |
898. | OCClF2 | C2H5-O-CH2-CH(CH3)- |
899. | OCClF2 | C2H5-S-CH2-CH(CH3)- |
900. | OCClF2 | C2H5-SO2-CH2-CH(CH3)- |
901. | OCClF2 | (CH3)2N-CH2-CH(CH3)- |
902. | OCClF2 | (C2H5)2N-CH2-CH(CH3)- |
903. | OCClF2 | [(CH3)2CH]2N-CH2-CH(CH3)- |
904. | OCClF2 | CH3-O-CH(CH3)-CH2- |
905. | OCClF2 | CH3-S-CH(CH3)-CH2- |
906. | OCClF2 | CH3-SO2-CH(CH3)-CH2- |
907. | OCClF2 | C2H5-O-CH(CH3)-CH2- |
908. | OCClF2 | C2H5-S-CH(CH3)-CH2- |
909. | OCClF2 | C2H5-SO2-CH(CH3)-CH2- |
910. | OCClF2 | (CH3)2N-CH(CH3)-CH2- |
911. | OCClF2 | (C2H5)2N-CH(CH3)-CH2- |
912. | OCClF2 | [(CH3)2CH]2N-CH(CH3)-CH2- |
913. | OCClF2 | CH3-O-CH2-CH2-CH2- |
914. | OCClF2 | CH3-S-CH2-CH2-CH2- |
915. | OCClF2 | CH3-SO2-CH2-CH2-CH2- |
916. | OCClF2 | C2H5-O-CH2-CH2-CH2- |
917. | OCClF2 | C2H5-S-CH2-CH2-CH2- |
918. | OCClF2 | C2H5-SO2-CH2-CH2-CH2- |
919. | OCClF2 | (CH3)2N-CH2-CH2-CH2- |
920. | OCClF2 | (C2H5)2N-CH2-CH2-CH2- |
921. | OCClF2 | CH3-O-CH2-C(CH3)2- |
922. | OCClF2 | CH3-S-CH2-C(CH3)2- |
R1 | R2 | |
923. | OCClF2 | CH3-SO2-CH2-C(CH3)2- |
924. | OCClF2 | C2H5-O-CH2-C(CH3)2- |
925. | OCClF2 | C2H5-S-CH2-C(CH3)2- |
926. | OCClF2 | C2H5-SO2-CH2-C(CH3)2- |
927. | OCClF2 | (CH3)2N-CH2-C(CH3)2- |
928. | OCClF2 | (C2H5)2N-CH2-C(CH3)2- |
929. | OCClF2 | [(CH3)2CH]2N-CH2-C(CH3)2- |
930. | OCClF2 | Cl-CH2-C≡C-CH2- |
931. | OCClF2 | CH3-O-C(O)-CH2 |
932. | OCClF2 | C2H5-O-C(O)-CH2 |
933. | OCClF2 | CH3-O-C(O)-CH(CH3)- |
934. | OCClF2 | C2H5-O-C(O)-CH(CH3)- |
935. | OCClF2 | (CH3O)2CH-CH2- |
936. | OCClF2 | (C2H5O)2CH-CH2- |
式I的2-氰基苯磺酰胺化合物例如可以通过使2-氰基苯磺酰卤II与氨或伯胺(III)类似于J.March,第4版,1992,第499页中所述的方法反应而制备(见方案1)。
方案1:
在方案1中,变量R1-R5如上所定义且Y为卤素,尤其是氯或溴。磺酰卤II,尤其是磺酰氯与胺III的反应通常在溶剂存在下进行。合适的溶剂是在反应条件下呈惰性的极性溶剂,例如C1-C4链烷醇,如甲醇、乙醇、正丙醇或异丙醇,二烷基醚如乙醚、二异丙醚或甲基叔丁基醚,环状醚如二烷或四氢呋喃,乙腈,羧酰胺如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或N-甲基吡咯烷酮,水,(条件是磺酰卤II在所用反应条件下充分耐水解)或其混合物。
通常而言,胺III基于磺酰卤II以至少等摩尔量使用,优选至少过量2倍摩尔量,以结合形成的卤化氢。可能有利的是基于磺酰卤II使用至多过量6倍摩尔量的伯胺III。
可能有利的是在辅助碱存在下进行该反应。合适的辅助碱包括有机碱,例如叔胺,如脂族叔胺如三甲胺、三乙胺或二异丙基胺,脂环族叔胺如N-甲基哌啶或芳族胺如吡啶,取代吡啶如2,3,5-三甲基吡啶、2,4,6-三甲基吡啶、2,4-二甲基吡啶、3,5-二甲基吡啶或2,6-二甲基吡啶以及无机碱如碱金属碳酸盐和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钠、碳酸钙,还有碱金属碳酸氢盐如碳酸氢钠。辅助碱与磺酰卤II的摩尔比优选为1∶1-4∶1,优选1∶1-2∶1。若该反应在辅助碱存在下进行,则伯胺III与磺酰卤II的摩尔比通常为1∶1-1.5∶1。
该反应通常在0℃至溶剂的沸点,优选0-30℃范围内的反应温度下进行。
若不能市购,则例如可以由下述方法之一制备磺酰卤化合物II。
磺酰氯化合物II的制备例如可以根据方案2所示的反应顺序进行,其中变量R1、R3-R5如上所定义:
方案2:
a)例如以类似于Liebigs Ann.Chem.1980,768-778中所述的方法通过如下方式将苯并异噻唑IV转化成硫醇V:使IV与碱反应,所述碱例如为碱金属氢氧化物和碱土金属氢氧化物如氢氧化钠、氢氧化钾和氢氧化钙,碱金属氢化物如氢化钠或氢化钾或醇盐如甲醇钠、乙醇钠等,所述反应在惰性有机溶剂,例如醚类如乙醚、二异丙基醚、四氢呋喃、二烷中进行,或在醇类如甲醇、乙醇、丙醇、异丙醇、丁醇、1,2-乙二醇、二甘醇中进行,或在羧酰胺如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或N-甲基吡咯烷酮中进行或在二甲亚砜中或在上述溶剂的混合物中进行;并酸化,得到硫醇V。苯并异噻唑IV可以类似于Liebig Ann.Chem729,146-151(1969)中所述的方法制备;以及随后
b)例如通过使硫醇V与氯气在水或水-溶剂混合物,例如水和乙酸的混合物中类似于Jerry March,第3版,1985,反应9-27,第1087页中所述的方法反应而将硫醇V氧化成磺酰氯II(Y=Cl)。
化合物II(其中Y为氯且R4和R5为氢)可以通过方案3中所示的反应顺序制备,其中变量R1具有上述含义且R3为H、Cl、Br、I或CN:
方案3:
c)例如类似于EP 945 449,Jerry March,第3版,1985,第476页,NeuereMethoden der organischen Chemie,第1卷,237(1944)或J.L.Wood,Organic Reactions,第III卷,240(1946)中所述的方法通过用硫化氰将苯胺VI硫氰化而制备氰硫基化合物VII;硫化氰通常例如通过使硫氰酸钠与溴在惰性溶剂中反应而就地制备。合适的溶剂包括链烷醇如甲醇或乙醇或羧酸如乙酸、丙酸或异丁酸及其混合物。优选惰性溶剂为其中可能已经加有一些用于稳定化的溴化钠的甲醇。
d)通过常规重氮化将VII中的氨基转化为重氮基,然后将重氮基转化成氢、氯、溴或碘或氰基。合适的亚硝化试剂是四氟硼酸亚硝鎓盐,亚硝酰氯,亚硝基硫酸,亚硝酸烷基酯如亚硝酸叔丁酯,或亚硝酸的盐如亚硝酸钠。所得重氮盐到其中R3=氰基、氯、溴或碘的对应化合物VIII的转化可以通过用铜(I)盐如氰化铜(I)、氯化铜(I)、溴化铜(I)或碘化铜(I)的溶液或悬浮液或碱金属盐的溶液处理VII而进行(例如参见Houben-Weyl,Methoden der organischen Chemie[有机化学方法],Georg Thieme Verlag Stuttgart,第5/4卷,第4版,1960,第438及随后各页)。所得重氮盐到其中R3=H的对应化合物VIII的转化例如可以通过用次磷酸(hypophosphous acid)、亚磷酸、亚锡酸钠处理或在非水介质中通过用氢化三丁基锡或(C2H5)3SnH或硼氢化钠处理而进行(例如参见Jerry March,第3版,1985,第646及随后各页)。
e)通过在硫酸存在下用锌处理或通过用硫化钠处理而将硫氰酸酯VIII还原成对应的硫醇化合物IX;和随后
f)类似于方案2的步骤b)将硫醇IX氧化,得到磺酰氯II。
此外,苯磺酰氯II(Y=Cl)可以通过方案4中所示的反应顺序制备,其中变量R1、R3、R4和R5如上所定义。
方案:
(g)例如类似于WO 00/29394中所述的方法将硝基甲苯X转化成苯甲醛肟化合物XI。X到XI的转化例如通过使硝基化合物X与其中R为烷基的有机亚硝酸酯R-ONO在碱存在下反应而实现。合适的亚硝酸酯为亚硝酸C2-C8烷基酯,如亚硝酸正丁酯或亚硝酸(异)戊酯。合适的碱是碱金属醇盐如甲醇钠、甲醇钾或叔丁醇钾,碱金属氢氧化物如NaOH或KOH或有机镁化合物如式R′MgX(R′=烷基,X=卤素)的格利雅试剂。该反应通常在惰性溶剂中进行,所述惰性溶剂优选包括极性非质子溶剂。合适的极性非质子溶剂包括羧酰胺如N,N-二烷基甲酰胺,例如N,N-二甲基甲酰胺,N,N-二烷基乙酰胺,例如N,N-二甲基乙酰胺或N-烷基内酰胺,例如N-甲基吡咯烷酮或其混合物或其与非极性溶剂如链烷烃、环烷烃和芳族溶剂如甲苯和二甲苯的混合物。当使用钠碱时,合适的话可以加入1-10mol%醇。化学计量比例如如下:1-4当量碱,1-2当量R-ONO;优选1.5-2.5当量碱和1-1.3当量R-ONO;同样优选1-2当量碱和1-1.3当量R-ONO。该反应通常在-60℃至室温,优选-50℃至-20℃,尤其是-35℃至-25℃下进行。
(h)例如类似于Jerry March,第4版,1992,第1038及随后各页中所述的程序通过用脱水试剂如乙酸酐、原甲酸乙酯和H+、(C6H5)3P-CCl4、氯甲酸三氯甲基酯、氰基甲酸甲基(或乙基)酯、三氟甲烷磺酸酐处理而将醛肟XI脱水得到腈XII;
(i)例如通过使硝基化合物XII与金属如铁、锌或锡或与SnCl2在酸性条件下反应、与复合氢化物如氢化铝锂和钠反应而将化合物XII还原为苯胺XIII。该还原可以在不稀释下或在溶剂或稀释剂中进行。取决于所选择的还原试剂,合适的溶剂例如为水,链烷醇如甲醇、乙醇和异丙醇,或醚类如乙醚、甲基叔丁基醚、二烷、四氢呋喃和乙二醇二甲醚。
化合物XII中的硝基还可以通过催化氢化转化为氨基(例如参见Houben Weyl,第IV/1c卷,第506及随后各页或WO 00/29394)。合适的催化剂例如为铂或钯催化剂,其中金属可以负载在惰性载体如活性炭、粘土、硅藻土、二氧化硅、氧化铝、碱金属或碱土金属碳酸盐等上。催化剂的金属含量基于载体可以在1-20重量%范围内变化。通常而言,基于硝基化合物XII使用0.001-1重量%的铂或钯,优选0.01-1重量%的铂或钯。该反应通常在没有溶剂下或在惰性溶剂或稀释剂中进行。合适的溶剂或稀释剂包括芳族化合物如苯、甲苯、二甲苯,羧酰胺如N,N-二烷基乙酰胺,例如N,N-二甲基甲酰胺,N,N-二烷基乙酰胺,例如N,N-二甲基乙酰胺或N-烷基内酰胺,例如N-甲基吡咯烷酮,四烷基脲,如四甲基脲、四丁基脲、N,N′-二甲基亚丙基脲和N,N′-二甲基亚乙基脲,链烷醇如甲醇、乙醇、异丙醇或正丁醇,醚类如乙醚、甲基叔丁基醚、二烷、四氢呋喃和乙二醇二甲醚,羧酸如乙酸或丙酸,羧酸酯如乙酸乙酯。反应温度通常为-20℃至100℃,优选0-50℃。氢化可以在大气氢压或升高的氢压下进行。
(k)将化合物XIII的氨基转化为对应的重氮基,然后使重氮盐与二氧化硫在氯化铜(II)存在下反应而得到磺酰氯II。重氮盐可以如方案3的步骤d)所述制备。优选将亚硝酸钠用作烷基亚硝酸盐。通常将二氧化硫溶于冰乙酸中。
式XIII化合物还可以根据WO 94/18980中所述的方法使用邻硝基苯胺作为前体或根据WO 00/059868使用靛红前体制备。
若各化合物I不能通过上述途径得到,则它们可以通过衍生其它化合物I或通过所述合成途径的常规改变而制备。
反应混合物以常规方式处理,例如通过与水混合,分离各相以及合适的话,可以利用在氧化铝或硅胶上的层析法提纯粗产物。一些中间体和终产物可能以无色或浅棕色粘稠油形式得到,将它们在减压和温和升高的温度下提纯或除去挥发性组分。若中间体和终产物以固体得到,则也可通过重结晶或浸提进行提纯。
由于通式I的化合物具有优异的活性,它们可以用于防治动物害虫。动物害虫包括有害昆虫和螨虫。因此,本发明进一步提供了用于对抗动物害虫,尤其是昆虫和/或螨虫的农用组合物,其包含杀虫作用量的至少一种通式I化合物和/或至少一种I的可农用盐和至少一种惰性液体和/或固体可农用载体以及需要的话至少一种表面活性剂。
该组合物可以含有一种本发明通式I的活性化合物或几种本发明活性化合物I的混合物。本发明的组合物可以包含单一的异构体或异构体混合物。
2-氰基苯磺酰胺化合物I和包含它们的杀虫组合物是防治动物害虫的有效试剂。由式I化合物防治的动物害虫例如包括:
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsia gemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographagamma)、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capuareticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneurafumiferana)、Choristoneura occidentalis、二化螟(Cirphis unipuncta)、苹果小卷蛾(Cydia pomonella)、松毛虫(Dendrolimus pini)、Diaphanianitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Eariasinsulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetria bouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothisvirescens)、玉米穗虫(Heliothis zea)、菜螟(Hellula undalis)、Hiberniadefoliaria、美国白蛾(Hyphantria cunea)、苹果巢蛾(Hyponomeutamalinellus)、番茄虫蛾(Keiferia lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletis blancardella、葡萄浆果小卷蛾(Lobesiabotrana)、甜菜网螟(Loxostege sticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、黄杉毒蛾(Orgyiapseudotsugata)、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophora gossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutella xylostella)、大豆夜蛾(Pseudoplusiaincludens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotrogacerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodopterafrugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodopteralitura)、Thaumatopoea pityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis;
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallussolstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、甜菜隐食甲(Atomaria linearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotomatrifurcata、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderusvespertinus、石刁柏负泥虫(Crioceris asparagi)、Diabrotica longicornis、Diabrotica 12-punctata、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ipstypographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lemamelanopus)、马铃薯叶甲(Leptinotarsa decemlineata)、Limoniuscalifornicus、稻水象甲(Lissorhoptrus oryzophilus)、Melanotus communis、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、辣根猿叶甲(Phaedon cochleariae)、Phyllotreta chrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popillia japonica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilusgranaria);
双翅目昆虫(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、剌扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anophelesmaculipennis)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、高粱瘿蚊(Contarinia sorghicola)、Cordylobia anthropophaga、尖音库蚊(Culexpipiens)、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilusintestinalis)、刺舌蝇(Glossina morsitans)、Haematobia irritans、Haplodiplosis equestris、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、麦瘿蚊(Mayetiola destructor)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、Phorbiaantiqua、萝卜蝇(Phorbia brassicae)、Phorbia coarctata、樱桃实蝇(Rhagoletis cerasi)、苹果实蝇(Rhagoletis pomonella)、Tabanus bovinus、Tipula oleracea和欧洲大蚊(Tipula paludosa);
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothrips corbetti)、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothrips citri)、稻蓟马(Thripsoryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci);
膜翅目昆虫(膜翅目(Hymenoptera)),如蚁、蜜蜂、黄蜂和锯蝇,例如新疆菜叶蜂(Athalia rosae)、切叶蚁(Atta cephalotes)、Atta sexdens、Attatexana、举腹蚁属(Crematogaster spp.)、Hoplocampa minuta、Hoplocampatestudinea、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsisgeminate)、红火蚁(Solenopsis invicta)、黑火蚁(Solenopsis richteri)、南方火蚁(Solenopsis xyloni)、红蚂蚁(Pogonomyrmex barbatus)、Pogonomyrmex californicus、天鹅绒蚂蚁(Dasymutilla occidentalis)、熊蜂属(Bombus spp.)、大黄蜂(Vespula squamosa)、Paravespula vulgaris、Paravespula pennsylvanica、Paravespula germanica、姬胡蜂(Dolichovespula maculate)、黄边胡蜂(Vespa crabro)、胡蜂(Polistes)、rubiginosa、Campodontus floridanus和Linepitheum humile(Linepithemahumile(阿根廷蚁));
异翅目昆虫(异翅目(Heteroptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygasterintegriceps)、Euschistus impictiventris、棉红铃喙缘蝽(Leptoglossusphyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubea insularis和Thyanta perditor;
同翅目昆虫(同翅目(Homoptera)),例如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、Aphis schneideri、卷叶蚜(Aphis spiraecola)、Aphis sambuci、豌豆蚜(Acyrthosiphon pisum)、马铃薯蚜(Aulacorthumsolani)、银叶粉虱(Bemisia argentifolii)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudusprunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosiphagossypii、Chaetosiphon fragaefolii、Cryptomyzus ribis、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulacorthum pseudosolani、Dysaphisplantaginea、Dysaphis pyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphumavenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphonrosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzusascalonicus)、Myzus cerasi、桃蚜(Myzus persicae)、李瘤蚜(Myzus varians)、Nasonovia ribis-nigri、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigusbursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodonhumuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、Rhopalosiphum insertum、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneuralanuginosa、麦长管蚜(Sitobion avenae)、白背飞虱(Sogatella furcifera)、白粉虱(Trialeurodes vaporariorum)、Toxoptera aurantiiand和葡萄根瘤蚜(Viteus vitifolii);
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermesflavipes、黄肢散白蚁(Reticulitermes flavipes)、欧洲散白蚁(Reticulitermeslucifugus)和Termes natalensis;
直翅目昆虫(直翅目(Orthoptera)),例如居屋艾蟋(Acheta domestica)、东方蜚蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、欧洲球螋(Forficula auricularia)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locustamigratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplusfemur-rubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲蟑螂(Periplaneta americana)、美洲沙漠蝗(Schistocerca americana)、Schistocerca peregrina、Stauronotusmaroccanus和庭疾灶螽(Tachycines asynamorus),
蜘蛛纲(Arachnoidea),如蜘蛛(蜱螨目(acarina)),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyomma americanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilusdecoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssusgallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),瘿螨属(Eriophyidaespp.),如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨属(Tarsonemidae spp.),如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨属(Tenuipalpidaespp.),如紫红短须螨(Brevipalpus phoenicis);叶螨属(Tetranychidae spp.),如朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri)和oligonychus pratensis;
蚤目(Siphonaptera),例如Xenopsylla cheopsis、角叶(Ceratophyllus)属。
式I化合物优选用于防治同翅目和缨翅目害虫。
式I化合物还优选用于防治膜翅目害虫。
式(I)化合物或包含它们的杀虫组合物可以通过使植物/作物与杀虫有效量的式(I)化合物接触而用于保护生长植物和作物免受动物害虫,尤其是昆虫或螨虫的侵袭或侵染。术语“作物”指生长和收获作物二者。
可以通过本领域已知的任何施用方法使动物害虫,尤其是昆虫、螨虫,植物和/或植物生长于其中的土壤或水与本发明化合物I或包含它们的组合物接触。因此,“接触”包括直接接触(将化合物/组合物直接施用于动物害虫,尤其是昆虫和/或螨虫上和/或植物—通常是植物的叶、茎或根上)和间接接触(将化合物/组合物施用于动物害虫,尤其是昆虫和/或螨虫的场所,和/或植物上)。
此外,动物害虫,尤其是昆虫或螨虫可以通过使目标害虫、其食物供应源或其场所与杀虫有效量的式(I)化合物接触而得到防治。因此,施用可以在该场所、生长作物或收获作物被害虫侵染之前或之后进行。
“场所”是指栖息地,繁殖地,害虫或寄生虫正生长或可能生长于其中的植物、种子、土壤、区域、材料或环境。
适用于本发明方法的有效量可以取决于特定的式I化合物,目标害虫,施用方法,施用时间,气候条件,动物害虫习性,尤其是昆虫或螨虫习性等而变化。通常而言,为了用于处理作物植株,本发明化合物I和/或组合物的施用率可以为约0.1至约4000g/公顷,理想的是约25至约600g/公顷,更理想的是约50至约500g/公顷。为了用于处理种子,典型的施用率是约1至约500g/kg种子,理想的是约2至约300g/kg种子,更理想的是约10至约200g/kg种子。在材料保护中的常规施用率例如为约0.001至约2000g活性化合物/立方米被处理材料,理想的是约0.005至约1000g活性化合物/立方米被处理材料。
化合物I或包含它们的杀虫组合物例如可以以溶液、乳液、微乳液、悬浮液、可流动浓缩物、粉剂、粉末、糊和颗粒形式使用。使用形式取决于特定的目的;在任何情况下应保证本发明化合物精细和均匀地分布。
用于对抗动物害虫,尤其是昆虫和/或螨虫的杀虫组合物含有至少一种通式I的化合物或I的可农用盐和常用于配制杀虫组合物的辅助剂。
配制剂以已知方式制备,例如通过将活性成分与溶剂和/或载体混合来制备,需要的话使用乳化剂和分散剂,若使用水作为稀释剂,则还可以使用其它有机溶剂作为辅助溶剂。适合的助剂主要是:溶剂如芳族化合物(如二甲苯),氯代芳族化合物(如氯苯),链烷烃(如矿物油馏分),醇(如甲醇、丁醇),酮(如环己酮),胺(如乙醇胺、二甲基甲酰胺)和水;载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐以及脂肪酸及其碱金属和碱土金属盐,硫酸化脂肪醇乙二醇醚的盐,磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚或甲醛的缩合物,聚氧乙烯辛基苯基醚,乙氧基化的异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备直接可喷溶液、乳液、糊或油分散体的物质是中沸点到高沸点的矿物油馏分,如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃,例如苯、甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、氯仿、四氯化碳、环己醇、环己酮、氯苯、异佛尔酮,强极性溶剂,例如二甲基甲酰胺、二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和粉剂可以通过将活性物质与固体载体混合或同时研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过将活性成分与固体载体粘附而制备。固体载体的实例是矿土如硅石、硅胶、硅酸盐、滑石、高岭土、活性白土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、尿素;植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉;纤维素粉和其它固体载体。
本发明的该类配制剂或组合物包括本发明的式I化合物(或其结合)以及与其相混合的一种或多种可农用惰性固体或液体载体。这些组合物含有杀虫有效量的所述化合物,该量可以取决于特定化合物、目标害虫和使用方法而变化。
通常而言,配制剂包含0.001-95重量%,优选0.1-90重量%的活性成分。活性成分以90-100%,优选95-100%的纯度(根据NMR波谱)使用。
示例性配制剂如下所述:
I.5重量份本发明化合物与95重量份细碎高岭土均匀混合。得到包含5重量%活性成分的粉剂。
II.将30重量份本发明化合物与由92重量份粉状硅胶和8重量份已经喷雾到该硅胶表面上的石蜡油组成的混合物均匀混合。得到具有良好粘附性能的活性成分配制剂(包含23重量%活性成分)。
III.将10重量份本发明化合物溶于由90重量份二甲苯、6重量份的8-10摩尔氧化乙烯与1摩尔油酸N-单乙醇酰胺的加合物、2重量份十二烷基苯磺酸钙和2重量份的40摩尔氧化乙烯与1摩尔蓖麻油的加合物组成的混合物中(包含9重量%活性成分)。
IV.将20重量份本发明化合物溶于由60重量份环己酮、30重量份异丁醇、5重量份的7摩尔氧化乙烯与1摩尔异辛基酚的加合物和5重量份的40摩尔氧化乙烯与1摩尔蓖麻油的加合物组成的混合物中(包含16重量%活性成分)。
V.将80重量份本发明化合物与3重量份二异丁基萘-α-磺酸钠、10重量份来自亚硫酸盐废液的木素磺酸的钠盐和7重量份粉状硅胶彻底混合并将该混合物在锤磨机中研磨(包含80重量%活性成分)。
VI.将90重量份本发明化合物与10重量份N-甲基-α-吡咯烷酮混合,得到适于以微滴形式使用的溶液(包含90重量%活性成分)。
VII.将20重量份本发明化合物溶于由40重量份环己酮、30重量份异丁醇、20重量份的7摩尔氧化乙烯与1摩尔异辛基苯酚的加合物和10重量份的40摩尔氧化乙烯与1摩尔蓖麻油的加合物组成的混合物中。将该溶液倾入100,000重量份水中并在其中精细分布,得到包含0.02重量%活性成分的水分散体。
VIII.将20重量份本发明化合物与3重量份二异丁基萘-α-磺酸钠、17重量份来自亚硫酸盐废液的木素磺酸的钠盐和60重量份粉状硅胶彻底混合,并将混合物在锤磨机中研磨。将该混合物在20,000重量份水中精细分散,得到包含0.1重量%活性成分的喷雾混合物。
活性成分可以通过喷雾、雾化、撒粉、撒播或浇灌直接使用,以其配制剂形式或由其制备的使用形式使用,例如以直接可喷溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、粉剂、撒播用材料或颗粒形式使用。使用形式完全取决于意欲的目的;在任何情况下都应确保本发明的活性成分尽可能精细地分布。
含水使用形式可以通过添加水由乳油、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为了制备乳液、糊或油分散体,可以通过湿润剂、增粘剂、分散剂或乳化剂将物质直接或溶于油或溶剂之后在水中均化。另外,可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话,溶剂或油组成的浓缩物且该类浓缩物适于用水稀释。
活性成分在即用产品中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性成分还可成功地以超低容量方法(ULV)使用,其中可以施用包含超过95重量%活性成分的配制剂或甚至可以在没有添加剂的情况下施用活性成分。
根据本发明使用的组合物还可以含有其他活性成分,例如其他杀虫剂、杀昆虫剂、除草剂、杀真菌剂、其他杀虫剂或杀菌剂,肥料如硝酸铵、尿素、钾碱和酸性磷酸盐,植物毒素和植物生长调节剂,安全剂和杀线虫剂。这些额外的成分可以顺序使用或与上述组合物结合使用,合适的话还可以在紧临使用之前加入(桶混合)。例如,可以在用其他活性成分处理之前或之后用本发明的组合物喷雾植物。
这些试剂可以与本发明试剂以1∶10至10∶1的重量比混合。将作为杀虫剂使用的化合物I或包含它们的组合物与其他杀虫剂混合通常导致更宽的杀虫作用谱。
下列本发明化合物可以与其一起使用的杀虫剂用来阐述可能的组合,而不施以任何限制:
有机磷酸酯类:高灭磷(Acephate)、谷硫磷(Azinphos-methyl)、毒死蜱(Chlorpyrifos)、毒虫畏(Chlorfenvinphos)、二嗪农(Diazinon)、敌敌畏(Dichlorvos)、百治磷(Dicrotophos)、乐果(Dimethoate)、乙拌磷(Disulfoton)、乙硫磷(Ethion)、杀螟松(Fenitrothion)、倍硫磷(Fenthion)、异唑磷(Isoxathion)、马拉硫磷(Malathion)、甲胺磷(Methamidophos)、杀扑磷(Methidathion)、甲基一六零五(Methyl-Parathion)、速灭磷(Mevinphos)、久效磷(Monocrotophos)、砜吸磷(Oxydemeton-methyl)、对氧磷(Paraoxon)、一六零五(Parathion)、稻丰散(Phenthoate)、伏杀磷(Phosalone)、亚胺硫磷(Phosmet)、磷胺(Phosphamidon)、甲拌磷(Phorate)、辛硫磷(Phoxim)、虫螨磷(Pirimiphos-methyl)、丙溴磷(Profenofos)、丙硫磷(Prothiofos)、乙丙硫磷(Sulprophos)、三唑磷(Triazophos)、敌百虫(Trichlorfon);
氨基甲酸酯类:棉铃威(Alanycarb)、丙硫克百威(Benfuracarb)、甲萘威(Carbaryl)、丁硫克百威(Carbosulfan)、双氧威(Fenoxycarb)、呋线威(Furathiocarb)、二唑虫(Indoxacarb)、灭虫威(Methiocarb)、灭多虫(Methomyl)、甲氨叉威(Oxamyl)、抗蚜威(Pirimicarb)、残杀威(Propoxur)、硫双威(Thiodicarb)、唑蚜威(Triazamate);
合成除虫菊酯类:氟氯菊酯(Bifenthrin)、氟氯氰菊酯(Cyfluthrin)、氯氰菊酯(Cypermethrin)、溴氰菊酯(Deltamethrin)、高氰戊菊酯(Esfenvalerate)、醚菊酯(Ethofenprox)、甲氰菊酯(Fenpropathrin)、杀灭菊酯(Fenvalerate)、(RS)氯氟氰菊酯(Cyhalothrin)、氯氟氰菊酯(Lambda-Cyhalothrin)、氯菊酯(Permethrin)、灭虫硅醚(Silafluofen)、氟胺氰菊酯(Tau-Fluvalinate)、七氟菊酯(Tefluthrin)、四溴菊酯(Tralomethrin)、己体氯氰菊酯(Zeta-Cypermethrin);
节肢动物生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类,如定虫隆(Chlorfluazuron)、氟脲杀(Difubenzuron)、氟螨脲(Flucycloxuron)、氟虫脲(Flufenoxuron)、氟铃脲(Hexaflumuron)、氟丙氧脲(Lufenuron)、双苯氟脲(Novaluron)、伏虫隆(Teflubenzuron)、杀虫隆(Triflumuron);噻嗪酮(Buprofezin)、茂醚(Diofenolan)、噻螨酮(Hexythiazox)、特苯唑(Etoxazole)、四螨嗪(Clofentazine);b)蜕皮激素拮抗剂:特丁苯酰肼(Halofenozide)、甲氧苯酰肼(Methoxyfenozide)、双苯酰肼(Tebufenozide);
c)保幼激素类似物:蚊蝇醚(Pyriproxyfen)、蒙五一五(Methoprene)、双氧威(Fenoxycarb);d)类脂生物合成抑制剂:螺螨酯(Spirodiclofen);
各种其它杀虫剂:齐墩螨素(Abamectin)、灭螨醌(Acequinocyl)、虫螨脒(Amitraz)、艾扎丁(Azadirachtin)、联苯肼酯(Bifenazate)、杀螟丹(Cartap)、氟唑虫清(Chlorfenapyr)、杀虫脒(Chlordimeform)、灭蝇胺(Cyromazine)、杀螨硫隆(Diafenthiuron)、呋虫胺(Dinetofuran)、茂醚(Diofenolan)、埃玛菌素(Emamectin)、硫丹(Endosulfan)、Ethiprole、喹螨醚(Fenazaquin)、锐劲特(Fipronil)、伐虫脒(Formetanate)、伐虫脒盐酸盐(Formetanatehydrochloride)、灭蚁腙(Hydramethylnon)、吡虫啉(Imidacloprid)、二唑虫(Indoxacarb)、哒螨酮(Pyridaben)、拒嗪酮(Pymetrozine)、艾克敌105(Spinosad)、硫(Sulfur)、吡螨胺(Tebufenpyrad)、噻虫嗪(Thiamethoxam)和硫环杀(Thiocyclam)。
现在通过下列实施例更详细描述本发明。
I.合成实施例
实施例1:正丙基-(2-氰基-3-甲基苯基)磺酰胺
1.1:2-氰基-3-甲基苯基磺酰氯
首先加入11.6g(88mmol)2-氨基-6-甲基苄腈(例如根据WO 94/18980制备)在120ml冰乙酸中的溶液并在室温下缓慢加入32.2g浓盐酸。将反应混合物在室温下搅拌10分钟,然后在5-10℃下滴加6.4g(92mmol)亚硝酸钠在20ml水中的溶液。将反应混合物在0℃下搅拌1小时,得到重氮盐。在分开的搅拌烧瓶中,在10℃下制备二氧化硫在冰乙酸中的饱和溶液并加入5.5g氯化铜(II)在11ml水中的溶液。然后将事先制备的重氮盐的反应混合物滴加到铜盐的溶液中。将所得混合物在室温下再搅拌45分钟。然后将反应混合物倾入冰冷的水中并用二氯甲烷萃取水相3次。将合并的有机层在干燥试剂上干燥并过滤。真空浓缩滤液得到16.4g(理论值的87%)标题化合物,熔点为75-77℃。
1.2:正丙基-(2-氰基-3-甲基苯基)磺酰胺
在室温下将1g(5mmol)2-氰基-3-甲基苯基磺酰氯在10ml四氢呋喃中的溶液加入630mg(11mmol)正丙胺在20ml四氢呋喃中的溶液中。将反应混合物在室温下搅拌3小时,然后加入水。水相用盐酸(浓度为10重量%,水溶液)酸化至pH=3,然后用二氯甲烷萃取3次。将合并的有机萃取液在硫酸钠上干燥并过滤。真空浓缩滤液得到850mg(理论值的85%)标题化合物,熔点为74-77℃。
实施例2:甲基-(2-氰基-3-甲氧基苯基)磺酰胺
2.1:2-氨基-6-甲氧基苄腈
首先加入70g(0.5mol)2-氨基-6-氟苄腈(例如根据US 4,504,660制备)在250ml N,N-二甲基甲酰胺中的溶液并在搅拌的同时在室温下滴加30.6g(0.55mol)甲醇钠在70ml甲醇中的溶液。然后在搅拌下回流混合物5小时。通过TLC监测反应的完成。加入在35ml甲醇中的额外25g甲醇钠并在搅拌下将反应混合物再回流4小时。将反应混合物在减压下浓缩,所得残余物用水研制,吸滤并将所得固体溶于乙酸乙酯中。真空浓缩所得溶液。将所得残余物用石油醚研制并吸滤,得到48g(理论值的63%)棕色固体,熔点为143-146℃。
2.2:2-氰基-3-甲氧基苯基磺酰氯
在搅拌的同时在室温下将10g浓盐酸缓慢加入4.0(27mmol)2-氨基-6-甲氧基苄腈在32ml冰乙酸中的溶液中。将混合物在室温下搅拌10分钟。然后在5-10℃下加入1.9g(27.3mmol)亚硝酸钠在5ml水中的溶液并将反应混合物在0℃下搅拌1小时,得到重氮盐。在分开的烧瓶中,在室温下制备二氧化硫在68ml冰乙酸中的饱和溶液并加入1.7g氯化铜(II)在4ml水中的溶液。然后将事先制备的重氮盐的反应混合物快速加入铜盐的溶液中。将所得混合物在室温下再搅拌2.5小时。然后将反应混合物倾入冰冷的水中。水层用二氯甲烷萃取3次。将合并的有机萃取液在干燥试剂上干燥并吸滤。将滤液真空浓缩,得到5.3g(理论值的85%)标题化合物,熔点为96-99℃。
2.3:甲基-(2-氰基-3-甲氧基苯基)磺酰胺
在室温下将1.25g(5.4mmol)2-氰基-3-甲氧基苯基磺酰氯在30ml四氢呋喃中的溶液加入960mg(12mmol)甲胺水溶液(40重量%)在20ml四氢呋喃中的溶液中。将反应混合物在室温下搅拌30分钟,然后加入水。使用盐酸(浓度为10重量%,水溶液)将水相酸化至pH=3。然后用二氯甲烷萃取水相3次。将合并的有机萃取液在硫酸钠上干燥并过滤。真空浓缩滤液并将所得残余物用甲基叔丁基醚研制,得到0.28g(理论值的23%)标题化合物,熔点为121-128℃。
实施例3:乙基-(4-氯-2-氰基-3-甲基苯基)磺酰胺
3.1:5-氯-6-甲基-2-硫氰基苄腈
将30g(190mmol)2-甲基-3-氰基-4-硫氰基苯胺(根据EP 0945449制备)溶于160ml冰乙酸中并在搅拌下缓慢滴加63g浓盐酸。将该混合物搅拌10分钟,然后在5-10℃下滴加11g(160mmol)亚硝酸钠在23ml水中的溶液而得到重氮盐。在分开的烧瓶中制备16g氯化铜(I)在50ml浓盐酸中的溶液。然后将已经事先制备的重氮盐的反应混合物快速滴加到铜盐的溶液中。所得反应混合物在室温下搅拌24小时。然后将反应混合物倾入冰冷的水中并用二氯甲烷萃取水相3次。将合并的有机层干燥、过滤,然后蒸发。所得粗产物通过在硅胶上柱层析(洗脱剂:甲苯/乙酸乙酯)进行提纯而得到14.3g(理论值的43%)标题化合物,熔点为78-80℃。
3.2:4-氯-2-氰基-3-甲基苯基磺酰氯
首先加入3.0g(21mmol)5-氯-6-甲基-2-硫氰酸酯基苄腈在20ml甲醇中的悬浮液,然后在将温度维持为20-35℃的同时加入1.9g(14mmol)硫化钠在8ml水中的溶液。将所得黄色溶液在室温下搅拌2天。然后用水稀释混合物并用甲基叔丁基醚萃取。通过加入浓盐酸将水相调节为pH=7,然后用二氯甲烷萃取。然后通过加入浓盐酸将水相调节为pH=1,随后用二氯甲烷萃取。将有机层干燥,过滤,然后浓缩。将所得残余物悬浮于20ml冰乙酸、5ml二氯甲烷和18ml水的混合物中,然后在25-45℃下在3小时内引入氯气流。用二氯甲烷稀释反应混合物并用冰冷的水洗涤有机相。在硫酸钠上干燥有机相,然后过滤并浓缩溶液得到1.3g(理论值的36%)的标题化合物,熔点为69-72℃。
3.3:乙基-(4-氯-2-氰基-3-甲基苯基)磺酰胺
首先加入770mg(12mmol)乙胺(70重量%)在20ml四氢呋喃中的水溶液,并在室温下滴加1.3g(5.2mmol)来自3.2.的4-氯-2-氰基-3-甲基苯基磺酰氯在10ml四氢呋喃中的溶液。将反应混合物在室温下搅拌2小时,用水稀释并通过加入盐酸(浓度为10重量%,水溶液)而调节为pH=3。将水相用二氯甲烷萃取3次。将合并的有机层用硫酸钠干燥、过滤,然后真空蒸发至干,得到0.5g(理论值的28%)棕色固体,熔点为85-90℃。
类似地制备列于下表1中的R4=H的式I化合物4-191以及列于下表2中的R5=H的式I化合物192和193。
表1:
实施例号 | R3 | R5 | R1 | R2 | m.p.[℃] |
1 | H | H | CH3 | n-CH2CH2CH3 | 74-77 |
2 | H | H | OCH3 | -CH3 | 121-128 |
3 | Cl | H | CH3 | -CH2CH3 | 85-90 |
4 | CN | CH3 | CH3 | -CH3 | 178-180 |
5 | Br | H | CH3 | -CH2CH3 | 112-114 |
6 | Br | H | CH3 | 环丙基 | 140-142 |
7 | Br | H | CH3 | n-C4H9 | 112-116 |
8 | Br | H | CH3 | -CH(CH3)2 | 102-103 |
9 | Br | H | CH3 | n-CH2CH2CH3 | 119-120 |
10 | Br | H | CH3 | C6H5-CH2- | 139-140 |
11 | Br | H | CH3 | 4-(CH3)3C-C6H4-CH2- | 147-151 |
12 | H | H | CH3 | C6H5-CH2- | 117-119 |
13 | H | H | CH3 | 4-(CH3)3C-C6H4-CH2- | 97-103 |
14 | H | H | CH3 | 4-Cl-C6H4-CH2- | 150-151 |
15 | Br | H | CH3 | 3-(CH3O)-C6H4-CH2- | 123-125 |
16 | H | H | CH3 | 3-(CH3O)-C6H4-CH2- | 117-122 |
17 | Br | H | CH3 | 4-(CH3O)-C6H4-CH2- | 156-161 |
18 | H | H | CH3 | 4-(CH3O)-C6H4-CH2- | 127-132 |
19 | Br | H | CH3 | 2-(CH3O)-C6H4-CH2- | 103-108 |
20 | H | H | CH3 | 2-(CH3O)-C6H4-CH2- | 127-130 |
21 | Br | H | CH3 | 4-Cl-C6H4-CH2- | 127-131 |
22 | Br | H | CH3 | 3-Cl-C6H4-CH2- | 102-108 |
23 | H | H | CH3 | 3-Cl-C6H4-CH2- | 118-125 |
24 | Br | H | CH3 | 2-Cl-C6H4-CH2- | 118-125 |
实施例号 | R3 | R5 | R1 | R2 | m.p.[℃] |
25 | H | H | CH3 | 2-Cl-C6H4-CH2- | 128-131 |
26 | Br | H | CH3 | 4-(F3C)-C6H4-CH2- | 153-155 |
27 | H | H | CH3 | 4-(F3C)-C6H4-CH2- | 135-137 |
28 | Br | H | CH3 | 环丙基-CH2- | 106-110 |
29 | H | H | CH3 | -CH3 | 83-89 |
30 | H | H | CH3 | -CH2CH3 | 98-103 |
31 | H | H | CH3 | 丙-2-炔基 | 104-107 |
32 | Br | H | CH3 | -CH2-CN | 106-110 |
33 | H | H | CH3 | 环丙基-CH2- | 89-93 |
34 | H | H | CH3 | -CH2-CN | 130-134 |
35 | Br | H | CH3 | 丙-2-炔基 | 1H-NMR |
36 | Br | H | CH3 | (CH3)3C-CH2- | 112-114 |
37 | H | H | CH3 | (CH3)3C-CH2- | 86-93 |
38 | H | H | CH3 | CH2=CHCH2- | 1H-NMR |
39 | H | H | OCH3 | -CH2CH3 | 121-126 |
40 | H | H | OCH3 | C6H5-CH2- | 108-119 |
41 | H | H | OCH3 | -CH(CH3)2 | 104-113 |
42 | H | H | OCH3 | 丙-2-炔基 | 122-138 |
43 | H | H | OCH3 | -CH2-CN | 1H-NMR |
44 | H | H | OCH3 | CH2=CHCH2- | 1H-NMR |
45 | H | H | OCH3 | H | 186-198 |
46 | Cl | H | CH3 | -CH3 | 112-122 |
47 | Cl | H | CH3 | H | 160-162 |
48 | H | H | OCH2CH3 | -CH3 | 91-95 |
49 | H | H | OCH2CH3 | -CH2CH3 | 111-113 |
50 | H | H | OCH2CH3 | H | 183-186 |
51 | Cl | H | CH3 | C6H5-CH2- | 132-135 |
52 | Cl | H | CH3 | -CH(CH3)2 | 86-94 |
53 | Cl | H | CH3 | 丙-2-炔基 | 1H-NMR |
54 | Cl | H | CH3 | H2C=CHCH2- | 95-96 |
55 | Cl | H | CH3 | FH2CCH2- | 115-121 |
56 | H | H | OCH2CH3 | C6H5-CH2- | 油 |
实施例号 | R3 | R5 | R1 | R2 | m.p.[℃] |
57 | H | H | OCH2CH3 | 丙-2-炔基 | 105-112 |
58 | H | H | OCH2CH3 | -CH2-CN | 129-134 |
59 | H | H | OCH2CH3 | CH2=CHCH2- | 油 |
60 | H | H | OCH2CH3 | -CH2-CH2-CH3 | 113-115 |
61 | H | H | OCH2CH3 | 环丙基-CH2 | 128-130 |
62 | Cl | H | CH3 | -CH2-CN | 134-138 |
63 | H | H | OCH2CH3 | -CH2-CF3 | 油 |
64 | H | H | OCH2CH=CH2 | -CH2-CH3 | 油 |
65 | H | H | OCH(CH3)2 | -CH2-CH3 | 油 |
66 | H | H | OCHF2 | -CH2-CH3 | 98-100 |
67 | H | H | OCH(CH3)2 | H | 132-136 |
68 | H | H | OCH(CH3)2 | 丙-2-炔基 | 油 |
69 | H | H | OCH(CH3)2 | -CH2CN | 油 |
70 | H | H | OCH(CH3)2 | 环丙基 | 油 |
71 | H | H | OCH(CH3)2 | -CH(CH3)2 | 油 |
72 | H | H | OCH(CH3)2 | C6H5-CH2- | 油 |
73 | H | H | OCH(CH3)2 | -CH2-CH3 | 油 |
74 | Br | H | CH3 | H | 149-151 |
75 | H | H | CH3 | H | 171-174 |
76 | H | H | OCH(CH3)2 | O-CH2-CH3 | 油 |
77 | H | H | OCH(CH3)2 | -CH2-CH2-CH3 | 油 |
78 | H | H | OCHF2 | H | 135-137 |
79 | H | H | OCHF2 | -CH2-C≡CH | 65-70 |
80 | H | H | OCH2CHClCH2Cl | H | 123-129 |
81 | H | H | OCH(CH3)2 | -CH3 | 82-91 |
82 | H | H | OCH3 | -CH2-c-C3H5 | 92-95 |
83 | H | H | OCH3 | -c-C3H5 | 142-148 |
84 | H | H | OCH3 | -O-CH2-CH3 | 138-143 |
85 | H | H | OCH3 | -CH2-CH2-CN | 123-130 |
86 | H | H | OCH3 | -CH2-CH2-S-CH3 | 油 |
87 | H | H | OCH3 | -CH2-CH2-S(O)2-CH3 | 157-160 |
88 | H | H | OCH3 | -CH2-CH2F | 134-140 |
实施例号 | R3 | R5 | R1 | R2 | m.p.[℃] |
89 | H | H | OCHF2 | H | 122-128 |
90 | H | H | OCH3 | -CH2-CF3 | 136-141 |
91 | H | H | OCH3 | -CH2-CHF2 | 116-118 |
92 | H | H | OCH3 | -O-CH3 | 136-139 |
93 | Br | H | OCH3 | -CH2-C≡CH | 110-115 |
94 | H | H | OCH3 | -CH2-CH2-N(CH3)2 | 94-97 |
95 | Br | H | OCH3 | -CH2-C6H5 | 134-136 |
96 | H | H | OCHF2 | -CH2-CF3 | 120-138 |
97 | H | H | OCHF2 | -CH2-C6H5 | 115-117 |
98 | H | H | OCHF2 | -c-C3H5 | 87-91 |
99 | H | H | OCHF2 | -CH2-CH2-S-CH3 | 1H-NMR |
100 | Br | H | OCHF2 | -CH3 | 168-173 |
101 | H | H | OCHF2 | -CH2-CH=CH2 | 75-78 |
102 | H | H | OCHF2 | -CH2-c-C3H5 | 1H-NMR |
103 | H | H | OCHF2 | -CH2-CH2-CH3 | 54-58 |
104 | H | H | OCHF2 | -CH2-CH2-O-CH3 | 1H-NMR |
105 | H | H | OCHF2 | -CH2-CH2-CN | 83-88 |
106 | H | H | OCHF2 | -CH-(CH3)2 | 72-74 |
107 | H | H | OCHF2 | -CH2-CHF2 | 92-96 |
108 | H | H | OCHF2 | -O-CH3 | 油 |
109 | H | H | CF3 | -CH2-CH3 | 81-86 |
110 | H | H | CF3 | -CH2-C≡CH | 106-111 |
111 | H | H | CF3 | -CH2-C6H5 | 106-108 |
112 | H | H | CF3 | -CH3 | 104-113 |
113 | H | H | CF3 | -CH2-CH=CH2 | 71-73 |
114 | H | H | CF3 | -CH-(CH3)2 | 65-67 |
115 | H | H | CF3 | -CH2-CH2-CH3 | 62-66 |
116 | H | H | CF3 | -CH2-c-C3H5 | 油 |
117 | H | H | CF3 | -CH2-CF3 | 油 |
118 | H | H | CF3 | -CH2-CH2-S-CH3 | 油 |
119 | H | H | CF3 | -c-C3H5 | 94-96 |
120 | H | H | CF3 | -O-CH2-CH3 | 118-120 |
实施例号 | R3 | R5 | R1 | R2 | m.p.[℃] |
121 | H | H | CF3 | -CH2-CH2-SO2-CH3 | 169-171 |
122 | H | H | CH3 | -O-CH2-CH3 | 118-121 |
123 | H | H | CH3 | -O-CH3 | 136-140 |
124 | H | H | CH3 | -环丁基 | HPLC/MS |
125 | H | H | CH3 | -环戊基 | HPLC/MS |
126 | H | H | CH3 | -环己基 | HPLC/MS |
127 | H | H | CH3 | -环丙基 | HPLC/MS |
128 | H | H | CH3 | -C(CH3)2-CH2-CH3 | HPLC/MS |
129 | H | H | CH3 | -CH2-CH2-CH2-N(C2H5)2 | HPLC/MS |
130 | H | H | CH3 | -CH(CH3)-CH(CH3)2 | HPLC/MS |
131 | H | H | CH3 | -CH(CH3)-C(CH3)3 | HPLC/MS |
132 | H | H | CH3 | -C(CH3)3 | HPLC/MS |
133 | H | H | CH3 | -C(CH3)(C2H5)-CH2-CH3 | HPLC/MS |
134 | H | H | CH3 | -C(CH3)2-CH2-CH2-CH3 | HPLC/MS |
135 | H | H | CH3 | -CH2-CH2-N[CH(CH3)2]2 | HPLC/MS |
136 | H | H | CH3 | -CH2-CH2-O-C2H5 | HPLC/MS |
137 | H | H | CH3 | -CH(C2H5)2 | HPLC/MS |
138 | H | H | CH3 | -CH(CH3)-CH2-CH(CH3)2 | HPLC/MS |
139 | H | H | CH3 | -CH(C2H5)-CH2-O-CH3 | HPLC/MS |
140 | H | H | CH3 | -C(CH3)2-C≡CH | HPLC/MS |
141 | H | H | CH3 | -CH(CH3)-CH2-O-C2H5 | HPLC/MS |
142 | H | H | CH3 | -CH(CH3)-CH2-O-CH3 | HPLC/MS |
143 | H | H | CH3 | -CH2-CH(CH3)-C2H5 | HPLC/MS |
144 | H | H | CH3 | -CH(CH3)-CH2-S-CH3 | HPLC/MS |
145 | H | H | CH3 | -CH2-CH(OCH3)2 | 1H-NMR |
146 | H | H | CH3 | -CH2-CH2-C(CH3)3 | HPLC/MS |
147 | H | H | CH3 | -CH2-CH(OC2H5)2 | HPLC/MS |
148 | H | H | CH3 | -CH2-CH2-S-CH3 | HPLC/MS |
149 | H | H | CH3 | -CH2-CH(CH3)2 | HPLC/MS |
150 | H | H | CH3 | -CH2-CH2-CH(CH3)2 | HPLC/MS |
151 | H | H | CH3 | -CH2-CH2-CH2-O-CH3 | HPLC/MS |
152 | H | H | CH3 | -CH2-CH(CH3)-O-CH3 | HPLC/MS |
实施例号 | R3 | R5 | R1 | R2 | m.p[℃] |
153 | H | H | CH3 | -CH2-CH(CH3)-CH2-C2H5 | HPLC/MS |
154 | H | H | CH3 | -CH2-CH2-CH2-S-CH3 | HPLC/MS |
155 | H | H | CH3 | -C(CH3)2-CH2-S-C2H5 | HPLC/MS |
156 | H | H | CH3 | -C(CH3)2-CH2-S-CH3 | HPLC/MS |
157 | H | H | CH3 | -CH(CH3)-CH2-N(CH3)2 | HPLC/MS |
158 | H | H | CH3 | -C(CH3)(n-C3H7)2-C≡CH | HPLC/MS |
159 | H | H | CH3 | -C(CH3)2-CH=CH2 | HPLC/MS |
160 | H | H | CH3 | -CH(CH3)-C(O)-O-CH3 | HPLC/MS |
161 | H | H | CH3 | -CH(CH3)-c-C3H5 | HPLC/MS |
162 | H | H | CH3 | -CH2-CF3 | HPLC/MS |
163 | H | H | CH3 | -CH2-CH2-O-CH3 | HPLC/MS |
164 | H | H | CH3 | -CH(CH3)-C2H5 | HPLC/MS |
165 | H | H | CH3 | CH(CH3)2 | HPLC/MS |
166 | H | H | CH3 | -C(CH3)2-CH2-CN | HPLC/MS |
167 | H | H | CH3 | -CH2-CH2-CH2-N(CH3)2 | HPLC/MS |
168 | H | H | CH3 | -CH2-CH2-CH2-CH2-CH3 | HPLC/MS |
169 | H | H | CH3 | -CH2-CH2-F | HPLC/MS |
170 | H | H | CH3 | -CH2-CH2-CH2-O-C2H5 | HPLC/MS |
171 | H | H | CH3 | -CH2-CH2-O-CH(CH3)2 | HPLC/MS |
172 | H | H | CH3 | -CH(CH3)-CH2-Cl | HPLC/MS |
173 | H | H | CH3 | -CH2-CH2-CH2-Cl | HPLC/MS |
174 | H | H | CH3 | -CH2-C≡C-CH2-Cl | HPLC/MS |
175 | H | H | CH3 | -CH2-C(O)-O-CH3 | HPLC/MS |
176 | H | H | CH3 | -CH2-CH2-CH2-Br | HPLC/MS |
177 | H | H | CH3 | -CH2-CH2-CH2-CH3 | HPLC/MS |
178 | H | H | CH3 | -CH2-CH2-S-C2H5 | HPLC/MS |
179 | CN | H | CH3 | -CH2-CH3 | 114-119 |
180 | CN | H | CH3 | -CH3 | 172-175 |
181 | CN | H | CH3 | -CH2-C≡CH | 95-105 |
182 | CN | H | CH3 | H | 油 |
183 | CN | H | CH3 | -CH2-CH=CH2 | 83-95 |
184 | CN | H | CH3 | -CH2-CH2-CH3 | 95-99 |
实施例号 | R3 | R5 | R1 | R2 | m.p.[℃] |
185 | CN | H | CH3 | -CH2-CH2-F | 油 |
186 | CN | H | CH3 | -环丙基 | 油 |
187 | CN | H | CH3 | -O-CH3 | 139-142 |
188 | OCH3 | H | CH3 | -CH2-CH3 | 171-174 |
189 | OCH3 | H | CH3 | -CH2-C≡CH | 151-155 |
190 | OCH3 | H | CH3 | -H | 171-180 |
191 | OCH3 | H | CH3 | -CH3 | 171-175 |
m.p.:熔点;
c-C3H5:环丙基;
n-C3H7:正丙基
某些化合物通过1H-NMR表征。信号以对四甲基硅烷的化学位移(ppm)、其多重性和其积分(给定氢原子的相对数)表征。使用下列缩写表征信号的多重性:m=多重峰,t=三重峰,d=双重峰和s=单重峰。
实施例35:2.06(t,1H),2.72(s,3H),3.92(m,2H),5,56(t,1H),7.85(d,1H),7.92(d,1H),CDCl3
实施例38:2.66(s,3H),3.67(m,2H),5.12(d,1H),5.21(d,1H),5.30(t,1H),5.74(m,1H),7.56(d,1H),7.62(t,1H),7.95(d,1H),CDCl3
实施例43:4.04(s,3H),4.13(d,2H),6.15(t,1H),7.30(m,1H),7.72(m,2H),CDCl3
实施例44:3.67(m,2H),4.04(s,3H),5.11(d,1H),5.23(m,2H),5.76(m,1H),7.23(dd,1H),7.68(m,2H),CDCl3
实施例53:2.07(m,1H),2.72(s,3H),3.95(m,2H),5.52(t,1H),7.72(d,1H),7.95(d,1H),CDCl3
实施例99:2.05(s,3H),2.66(t,2H),3.28(q,2H),5.62(t,1H),6.73(t,1H),7.59(d,1H),7.77(t,1H),7.99(d,1H),CDCl3
实施例102:0.13(m,2H),0.31(m,2H),0.90(m,1H),2.95(t,2H),5.32(t,1H),6.72(t,1H),7.57(d,1H),7.77(t,1H),8.00(d,1H),CDCl3
实施例104:3.27(s,3H),3.33(m,2H),3.43(m,2H),5.56(t,1H),6.75(t,1H),7.58(d,1H),7.77(t,1H),8.00(d,1H),CDCl3
实施例145:2.65(s,3H),3.15(pt,2H),3.3(s,6H),4.35(t,1H),5.65(t,1H)7.55(d,1H),7.6(t,1H),7.9(d,1H),CDCl3
某些化合物通过联用的高效液相色谱法/质谱法(HPLC/MS)表征。
HPLC柱:RP-18柱(Chromolith Speed ROD,购自德国Merck KgaA)。
洗脱:乙腈+0.1%三氟乙酸(TFA)/水,比例为5∶95-95∶5,40℃,5分钟。
MS:四级电喷雾离子化,80V(正模式)
实施例124:2.813分钟,m/z=273[M+Na]+
实施例125:3.043分钟,m/z=287[M+Na]+
实施例126:3.260分钟,m/z=279[M+H]+
实施例127:2.486分钟,m/z=237[M+H]+
实施例128:3.198分钟,m/z=267[M+H]+
实施例129:1.955分钟,m/z=310[M+H]+
实施例130:3.244分钟,m/z=267[M+H]+
实施例131:3.438分钟,m/z=281[M+H]+
实施例132:3.004分钟,m/z=253[M+H]+
实施例133:3.483分钟,m/z=303[M+H]+
实施例134:3.533分钟,m/z=281[M+H]+
实施例135:2.091分钟,m/z=324[M+H]+
实施例136:2.534分钟,m/z=269[M+H]+
实施例137:3.154分钟,m/z=267[M+H]+
实施例138:3.413分钟,m/z=303[M+H]+
实施例139:2.761分钟,m/z=283[M+H]+
实施例140:2.740分钟,m/z=263[M+H]+
实施例141:2.802分钟,m/z=283[M+H]+
实施例142:2.596分钟,m/z=269[M+H]+
实施例143:3.225分钟,m/z=267[M+H]+
实施例144:3.836分钟,m/z=285[M+H]+
实施例146:3.430分钟,m/z=281[M+H]+
实施例147:2.934分钟,m/z=335[M+Na]+
实施例148:2.677分钟,m/z=271[M+H]+
实施例149:2.989分钟,m/z=253[M+H]+
实施例150:3.254分钟,m/z=267[M+H]+
实施例151:2.443分钟,m/z=269[M+H]+
实施例152:2.481分钟,m/z=269[M+H]+
实施例153:3.501分钟,m/z=281[M+H]+
实施例154:2.750分钟,m/z=285[M+H]+
实施例155:3.362分钟,m/z=335[M+Na]+
实施例156:3.116分钟,m/z=321[M+Na]+
实施例157:1.740分钟,m/z=282[M+H]+
实施例158:3.249分钟,m/z=291[M+H]+
实施例159:2.985分钟,m/z=265[M+H]+
实施例160:2.364分钟,m/z=283[M+H]+
实施例161:2.919分钟,m/z=265[M+H]+
实施例162:2.644分钟,m/z=301[M+Na]+
实施例163:2.177分钟,m/z=255[M+H]+
实施例164:2.917分钟,m/z=253[M+H]+
实施例165:2.570分钟,m/z=239[M+H]+
实施例166:2.500分钟,m/z=278[M+H]+
实施例167:3.314分钟,m/z=282[M+H]+
实施例168:3.297分钟,m/z=267[M+H]+
实施例169:2.259分钟,m/z=243[M+H]+
实施例170:2.709分钟,m/z=283[M+H]+
实施例171:2.814分钟,m/z=283[M+H]+
实施例172:2.733分钟,m/z=273[M+H]+
实施例173:2.729分钟,m/z=273[M+H]+
实施例174:2.743分钟,m/z=283[M+H]+
实施例175:2.187分钟,m/z=269[M+H]+
实施例176:2.935分钟,m/z=317[M+H]+
实施例177:3.090分钟,m/z=253[M+H]+
实施例178:2.956分钟,m/z=285[M+H]+
表2:
实施例号 | R3 | R4 | R1 | R2 | m.p.[℃] |
191 | H | Cl | CH3 | CH2CH3 | 119-123 |
192 | H | Br | CH3 | CH2CH3 | 141-144 |
II.对害虫的作用实施例
式I化合物对害虫的作用通过下列试验证实:
桃蚜(即Myzus persicae)
在50∶50丙酮∶水和100ppm Kinetic表面活性剂中配制活性化合物。
通过将侵染的叶片置于试验植物的顶部而将第2对叶阶段的辣椒植物(栽培品种为‘California Wonder’)用约40只实验室饲养的蚜虫侵染。24小时后移走所述叶片。将整个植物的叶子浸入试验化合物的梯度溶液中并进行干燥。在约25℃和20-40%相对湿度下将试验植物维持在荧光下(24小时光照)。5天后测定已处理植物上的蚜虫死亡率,相对于对照植物上的死亡率。
在该试验中,化合物1、2、3、5、12、23、29、30、31、33、37、38、39、40、41、42、43、45、46、47、48、49、50、52、53、54和55在300ppm下与未处理对照相比显示出超过85%的死亡率。
棉蚜(即Aphis gossypii)
在50∶50丙酮∶水和100ppm Kinetic表面活性剂中配制活性化合物。
通过将来自主群体的重度侵染叶子置于各子叶的顶部而将子叶阶段的棉花植物(栽培品种‘Delta Pine’,每盆一株)侵染。使蚜虫在一夜内转移到宿主植株上并移走用于转移蚜虫的叶子。将子叶浸入试验溶液中并进行干燥。5天后计数死亡率。
在该试验中,化合物2、3、5、6、8、10、12、13、14、15、16、18、19、20、21、22、23、24、25、27、28、29、30、31、32、35、36、37、38、39、40、41、42、43、44、45、46、47、48、49、50、51、52、53、54和55在300ppm下与未处理对照相比显示出超过85%的死亡率。
蚕豆蚜(即甜菜蚜(Aphis fabae))
在50∶50丙酮∶水和100ppm Kinetic表面活性剂中配制活性化合物。
通过将侵染的切割植物置于试验植物的顶部而将在Metro混合物中生长的第一对叶阶段的旱金莲属植物(栽培品种为‘Mixed Jewel’)用约2-30只实验室饲养的蚜虫侵染。24小时后移走所述切割植物。将各植物浸入试验溶液中以完全覆盖叶、茎、突出的种子表面和周围的立方体表面并在通风橱中进行干燥。将处理过的植物保持在约25℃和连续荧光下。3天后测定蚜虫死亡率。
在该试验中,化合物30、38、5、6、7、8、23、29、32、33、34、35、40、41、42和45在300ppm下与未处理对照相比显示出超过85%的死亡率。
银叶粉虱(即Bemisia argentifolii)
在50∶50丙酮∶水和100ppm Kinetic表面活性剂中配制活性化合物。
使选定的棉花植物生长到子叶状态(每盆一株)。将子叶浸入试验溶液中以完全覆盖叶面并置于通风良好的区域以干燥。将带有被处理秧苗的各盆置于塑料杯中并引入10-12只粉虱成虫(约3-5日龄)。使用吸气器和连接于防渗移液管尖端的0.6cm无毒Tygon管(R-3603)收集昆虫。然后将含有收集的昆虫的该尖端轻柔地插入含有被处理植物的土壤中,使昆虫由该尖端爬出而到达叶面进食。杯子用可再利用的筛网盖(150微米筛孔的聚酯筛网PeCap,购自Tetko Inc)覆盖。在约25℃和20-40%湿度下将试验植物在保持室中维持3天,避免直接暴露于荧光(24小时光照期),以防止在杯子内蓄积热。植物处理3天后评价死亡率。
在该试验中,化合物5和42在300ppm下与未处理对照相比显示出超过70%的死亡率。
二斑叶螨(即二点叶螨(Tetranychus urticae),耐OP的品系)
通过在各植物上放置一小片取自主群体的侵染叶子(约100个螨虫)而将主叶生长至7-12cm的利马豆(Sieva lima bean)植物(栽培品种‘Henderson’)侵染。这在处理之前约2小时进行,以使螨虫移到试验植物上产卵。移走用于转移螨虫的叶片。将新侵染的植物浸入试验溶液中并进行干燥。在约25℃和20-40%相对湿度下将试验植物保持在荧光下(24小时光照期)。5天后取出一片叶并计数死亡率。
在该试验中,化合物8和30在300ppm下与未处理对照相比显示出超过75%的死亡率。
佛州木工蚁(即Camponotus floridanus)
在陪替氏培养皿中进行试验。给予蚁以水源,然后禁食24小时。用20%蜂蜜/水溶液制备饵料。加入活性成分在丙酮中的溶液以获得1重量%(w/w)的活性成分浓度。向各培养皿中加入置于帽盖中的0.2ml含活性成分的蜂蜜/水溶液。将各培养皿覆盖并维持在22℃的水温下。每天观察蚁的死亡率。10天后测定死亡率。
在这些试验中,与未处理对照相比,化合物66、78和79显示出超过85%的死亡率。
阿根廷蚁(即Linepithema humile)
a)在陪替氏培养皿中进行试验。给予蚁以水源,然后禁食24小时。用20%蜂蜜/水溶液制备料饵。加入活性成分在丙酮中的溶液以获得1重量%(w/w)的活性成分浓度。向各培养皿中加入置于帽盖中的0.2ml含活性成分的蜂蜜/水溶液。将各培养皿覆盖并维持在22℃的水温下。每天观察蚁的死亡率。10天后测定死亡率。
在这些试验中,与未处理对照相比,化合物66、78和79显示出100%的死亡率。
b)如实施例a)中所述进行试验。将根据EP 33984的下列化合物I和II用作对比例。6天后观察蚁的死亡率。结果示于表3中。
对比例I 对比例II
表3:对阿根廷蚁(Linepithema humile)的生物活性
处理 | ai%1)(w/w) | 处理6天后的平均累计死亡率%2) |
化合物66 | 1.0 | 100.0 |
对比例I | 1.0 | 35.6 |
对比例II | 1.0 | 35.6 |
对照2) | na | 17.8 |
1)活性成分百分数
2)各自基于45只蚁(3次重复/处理)。
Claims (17)
1.通式I的2-氰基苯磺酰胺化合物和/或其可农用盐:
其中
R1为C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R2为氢、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C8环烷基或C1-C4烷氧基,其中后提到的五个基团可以未被取代、部分或完全被卤代和/或可以带有1、2或3个选自C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4烷氧羰基、氰基、氨基、(C1-C4烷基)氨基、二(C1-C4烷基)氨基、C3-C8环烷基和苯基的基团,其中苯基可以未被取代、部分或完全被卤代和/或带有1、2或3个选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基的取代基;和
R3、R4和R5相互独立地选自氢、卤素、氰基、硝基、C1-C6烷基、C3-C8环烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷氧基,C1-C4卤代烷硫基、C2-C6链烯基、C2-C6炔基、C1-C4烷氧羰基、氨基、(C1-C4烷基)氨基、二(C1-C4烷基)氨基、氨基羰基、(C1-C4烷基)氨基羰基和二(C1-C4烷基)氨基羰基。
2.如权利要求1所要求的化合物,其中在式I中,R1为C1-C2烷基或C1-C2烷氧基。
3.如权利要求2所要求的化合物,其中在式I中,R1为甲基。
4.如权利要求2所要求的化合物,其中在式I中,R1为甲氧基。
5.如权利要求1所要求的化合物,其中在式I中,R1为C1-C4卤代烷氧基。
6.如权利要求5所要求的化合物,其中在式I中,R1为C1卤代烷氧基,尤其是二氟甲氧基。
7.如权利要求1所要求的化合物,其中在式I中,R2选自氢、具有1-4个碳原子的烃基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基和C2-C4炔基。
8.如权利要求5所要求的化合物,其中R2为氢、甲基、乙基、1-甲基乙基或丙-2-炔-1-基。
9.如权利要求1所要求的化合物,其中在式I中,基团R3、R4和R5中至少一个不为氢。
10.如权利要求9所要求的化合物,其中R3为卤素。
11.如权利要求1所要求的化合物,其中在式I中,基团R3、R4或R5代表氢。
12.一种农用组合物,包含杀虫作用量的至少一种如权利要求1所定义的通式I化合物和/或至少一种I的可农用盐和至少一种惰性液体和/或固体可农用载体以及需要的话至少一种表面活性剂。
13.一种对抗动物害虫的方法,包括使动物害虫,其栖息地,繁殖地,食物供应源,动物害虫生长或可能生长于其中的植物、种子、土壤、区域、材料或环境或需要防止动物侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种通式I的2-氰基苯磺酰胺化合物和/或至少一种其可农用盐接触。
14.如权利要求13所定义的方法,其中动物害虫选自同翅目。
15.如权利要求13所定义的方法,其中动物害虫选自膜翅目。
16.如权利要求13所定义的方法,其中动物害虫选自缨翅目。
17.一种保护作物免受动物害虫侵袭或侵染的方法,包括使作物与杀虫有效量的至少一种如权利要求1所定义的通式I的2-氰基苯磺酰胺化合物和/或至少一种其盐接触。
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Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3997603A (en) * | 1972-04-12 | 1976-12-14 | E. I. Du Pont De Nemours And Company | Herbicidal halo-di-alkyl benzenesulfonamides |
US3888897A (en) * | 1972-04-12 | 1975-06-10 | Du Pont | Cyano-and cyanomethyl-benzensulfonamides |
EP0033984B1 (en) * | 1980-01-23 | 1984-06-06 | Duphar International Research B.V | New sulphonyl compounds, method of preparing the new compounds, as well as aphicidal compositions on the basis of the new compounds |
WO1997000857A1 (fr) * | 1995-06-21 | 1997-01-09 | Otsuka Kagaku Kabushiki Kaisha | Derives de sulfonamides et insecticide, miticide et nematicide les contenant |
EA200700972A1 (ru) * | 2004-11-26 | 2007-12-28 | Басф Акциенгезельшафт | Новые 2-циано-3-(гало)алкоксибензолсульфонамидные соединения для борьбы с животными-вредителями |
CA2601072A1 (en) * | 2005-03-24 | 2006-09-28 | Basf Aktiengesellschaft | 2-cyanobenzenesulfonamide compounds for seed treatment |
-
2004
- 2004-01-10 UA UAA200604611A patent/UA79404C2/uk unknown
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- 2004-10-01 CN CNA2004800288418A patent/CN1863767A/zh active Pending
- 2004-10-01 KR KR1020067006364A patent/KR20060101462A/ko not_active Application Discontinuation
- 2004-10-01 BR BRPI0414897-5A patent/BRPI0414897A/pt not_active Application Discontinuation
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102924412A (zh) * | 2008-01-25 | 2013-02-13 | 先正达参股股份有限公司 | 用作杀虫剂的2-氰基苯基磺酰胺衍生物 |
CN103467411A (zh) * | 2008-03-04 | 2013-12-25 | 先正达参股股份有限公司 | 具有农药特性的2-氰基苯磺酰胺衍生物 |
CN103491776A (zh) * | 2010-12-30 | 2014-01-01 | 拜耳知识产权股份有限公司 | 芳基、杂芳基和苄基磺酰胺的开链羧酸、碳酸酯、甲酰胺和腈或其盐用于提高植物胁迫耐受性的用途 |
CN106008288A (zh) * | 2016-06-15 | 2016-10-12 | 西北农林科技大学 | 一种苯磺酰胺类化合物及其用途 |
CN110218167A (zh) * | 2019-07-10 | 2019-09-10 | 河南科技大学 | N,n-二甲基芳香基磺酰胺类衍生物及其在防治南方根结线虫方面的应用 |
CN110218167B (zh) * | 2019-07-10 | 2021-09-24 | 河南科技大学 | N,n-二甲基芳香基磺酰胺类衍生物及其在防治南方根结线虫方面的应用 |
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AU2004279549A1 (en) | 2005-04-21 |
UY28545A1 (es) | 2005-04-29 |
AR046047A1 (es) | 2005-11-23 |
UA79404C2 (en) | 2007-06-11 |
ECSP066453A (es) | 2006-11-16 |
US20070071782A1 (en) | 2007-03-29 |
IL174151A0 (en) | 2006-08-01 |
KR20060101462A (ko) | 2006-09-25 |
CR8296A (es) | 2006-07-14 |
TW200526558A (en) | 2005-08-16 |
WO2005035486A1 (en) | 2005-04-21 |
BRPI0414897A (pt) | 2006-12-12 |
PE20050615A1 (es) | 2005-07-22 |
AP2006003568A0 (en) | 2006-04-30 |
EP1670752A1 (en) | 2006-06-21 |
MA28119A1 (fr) | 2006-08-01 |
CA2539563A1 (en) | 2005-04-21 |
JP2007507459A (ja) | 2007-03-29 |
JP4384175B2 (ja) | 2009-12-16 |
EA200600606A1 (ru) | 2006-08-25 |
ZA200603329B (en) | 2007-07-25 |
MXPA06003145A (es) | 2006-06-14 |
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