CN1216874C - (杂)芳基取代的杂环烯胺酮类化合物、其制备方法和其作为除草剂、杀螨剂和杀虫剂的应用 - Google Patents
(杂)芳基取代的杂环烯胺酮类化合物、其制备方法和其作为除草剂、杀螨剂和杀虫剂的应用 Download PDFInfo
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- CN1216874C CN1216874C CN008166757A CN00816675A CN1216874C CN 1216874 C CN1216874 C CN 1216874C CN 008166757 A CN008166757 A CN 008166757A CN 00816675 A CN00816675 A CN 00816675A CN 1216874 C CN1216874 C CN 1216874C
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- 125000000623 heterocyclic group Chemical class 0.000 title abstract description 3
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- 238000000034 method Methods 0.000 claims abstract description 79
- 239000001257 hydrogen Substances 0.000 claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 61
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 59
- 239000001301 oxygen Substances 0.000 claims abstract description 53
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- 238000007493 shaping process Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
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- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
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- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
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- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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- 229940074152 thuringiensin Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 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
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical class CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
本发明涉及新的通式(I)的杂环烯胺酮类化合物,其中,K代表氧或硫,Ar代表各自被取代的苯基或萘基,或代表各自任选被取代的具有5-10个环原子的单-或双环杂芳基,V代表氧或基团-S(O)n-或>N-W,X代表CN、(a)或(b),Y1和Y3相互独立地代表氢、卤素或各自任选被取代的烷基、烷氧基、烷氧基烷基、苯基、苯基烷基、杂芳基、杂芳基烷基或代表基团(c)或(d),Y2、Y4和Y6相互独立地代表氢、卤素或任选被取代的烷基,Y5代表氢或各自任选被取代的烷基或苯基,或Y4和Y5与它们所连的碳原子一起代表任选被取代的饱和或不饱和的环,该环任选地被杂原子间断,或Y1和Y2与它们所连的碳原子一起代表任选被取代的饱和或不饱和的环,该环任选地被杂原子间断,Z代表氢,代表各自任选被取代的烷基、链烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、苯氧基烷基、苯基烷基氧基烷基、苯硫基烷基、苯基烷基硫基烷基、苯基、苯基烷基、杂芳基、杂芳基烷基或代表基团(e;f;g;h;i;j;k)或氰基,以及m代表0-2;本发明还涉及这些化合物作为除草剂、杀螨剂和杀虫剂的应用以及制备这些化合物的方法。
Description
本发明涉及新的芳基取代的杂环烯胺酮类化合物、它们的多种制备方法、中间体以及它们作为作物保护剂、特别是除草剂、杀螨剂、杀线虫剂和杀虫剂的应用。
一些在苯基环中被取代的碳环烯胺酮类化合物作为抗菌活性喹喏酮的中间体已被公开(R.G.Glushkov,N.B.Marchenko,A.N.Padeiskaya,L.D.Shipilova,Pharm.Chem.J.(Engl.Transl.)24,460-465(1990))。在苯基环中未被取代的碳环烯胺酮类化合物也是已知的(M.V.Mezentseva,A.V.Kadushkin,L.M.Alekseeva,A.S.Sokolova,V.G.Granik,Pharm.Chem.J.(Engl.Transl.)25,858-864(1991);G.M.Coppola,R.Damon,A.D.Kahle,M.J.Shapiro,J.Org.Chem.,46,1221-1222(1981);D.Brillon,G.Sauvé,J.Org.Chem.,55,2246-2249(1990))。这些化合物作为作为保护剂的应用迄今为止还未被描述。
一般,所述的新的杂环烯胺酮类化合物用通式(I)表示:
其中
K代表氧或硫,
Ar代表各自被取代的苯基或萘基,或代表各自任选被取代的具有5-10个环原子的单-或双环杂芳基,
V代表氧或基团-S(O)n-或>N-W,
W代表氢、任选被取代的烷基、链烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、烷氧基、苯基烷氧基、苯基、苯基烷基、杂芳基、杂芳基烷基或代表基团-COR1,-CO2R1,-SO2R1,
或氰基,
X代表CN,
或
Y1和Y3相互独立地代表氢、卤素或各自任选被取代的烷基、烷氧基、烷氧基烷基、苯基、苯基烷基、杂芳基、杂芳基烷基或代表下列基团:
Y2、Y4和Y6相互独立地代表氢、卤素或任选被取代的烷基,
Y5代表氢或各自任选被取代的烷基或苯基,或
Y4和Y5与它们所连的碳原子一起代表任选被取代的饱和或不饱和的环,该环任选地被杂原子间断,或
Y1和Y2与它们所连的碳原子一起代表任选被取代的饱和或不饱和的环,该环任选地被杂原子间断,
Z代表氢,代表各自任选被取代的烷基、链烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、苯氧基烷基、苯基烷基氧基烷基、苯硫基烷基、苯基烷基硫基烷基、苯基、苯基烷基、杂芳基、杂芳基烷基或代表下列基团:
-CO2R1;
-SO2R1;-COR1;
或氰基,
l代表0-3,
m代表0-2,
n代表0-2,
R1代表氢,代表各自任选被取代的饱和或不饱和的烷基或环烷基,它们各自任选地被杂原子间断,代表各自任选被取代的苯基或杂芳基,代表各自任选被取代的苯基烷基或杂芳基烷基,
R2代表氢,代表各自任选被取代的饱和或不饱和的烷基或烷氧基,代表各自任选被取代的苯基、苯基烷基或苯基烷氧基,
R1和R2此外与它们所连的氮原子一起可以代表任选被取代的环,该环任选被杂原子间断,或
R3代表氢,代表各自任选被取代的烷基或烷氧基,代表各自任选被取代的苯基或苯基烷基,
R4代表氢或代表各自任选被取代的烷基,
R5和R6相互独立地代表氢或代表任选被取代的烷基。
对于通式(I)化合物:
Ar优选代表Ar1,该Ar1代表苯基、萘基或具有5-10个环原子的单-或双环杂芳基,这些基团各自任选地被下列基团单-至五取代:卤素、C1-C8-烷基、C2-C8-链烯基、C2-C8-炔基、C1-C8-烷氧基、C2-C8-链烯基氧基、C3-C8-炔基氧基、C1-C8-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C8-卤代链烯基氧基、C1-C2-亚烷二氧基、C1-C2-卤代亚烷二氧基、卤代-C1-C4-烷硫基、卤代-C1-C4-烷基亚磺酰基、卤代-C1-C4-烷基磺酰基、羟基、巯基、硝基、氰基、氨基或下列基团:
a)-L-CO-R7,
或代表Ar2,该Ar2代表Ar1,该Ar1还被下列基团取代:苯基、萘基、五-或六元杂芳基、苯基-C1-C4-烷基、苯基-C1-C4-烷氧基、苯基-C1-C4-烷基-S(O)p-、五-或六元杂芳基-C1-C4-烷氧基、五-或六元杂芳基-C1-C4-烷基-S(O)p-、苯氧基、苯基-S(O)p-、五-或六元杂芳氧基或杂芳基-S(O)p-,其中这些取代基本身各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基单-至四取代。
K优选代表氧或硫。
L优选代表氧或硫。
V优选代表氧或代表-S(O)n-或>N-W。
W优选代表氢,代表各自任选被氟和/或氯取代的C1-C8-烷基、C3-C8-链烯基、C3-C8-炔基、C3-C8-环烷基、C3-C8-环烷基-C1-C2-烷基、C1-C6-烷氧基、C1-C4-烷氧基-C2-C4-烷基,代表苯基、C1-C4-苯基烷基、C1-C4-苯基烷氧基、杂芳基、杂芳基烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基单-至四取代,或代表下列各式基团:
或氰基。
Y1和Y3相互独立地优选代表氢、卤素、C1-C6-烷基、C1-C4-卤代烷基、C1-C6-烷氧基、C1-C6-烷氧基-C1-C2-烷基,代表苯基、苯基-C1-C4-烷基、五-或六元杂芳基或五-或六元杂芳基-C1-C4-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基单-至四取代,或代表下列基团:
-CO2R1或
Y2、Y4、Y6相互独立地优选代表氢、卤素或代表被氟或氯取代的C1-C6-烷基。
Y5优选代表氢,代表任选被氟取代的C1-C6-烷基或代表任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基单-至四取代的苯基,或
Y4和Y5与它们所连的碳原子一起优选代表5-至8-元饱和或不饱和的环,该环可以被1-3个选自N、O和S的杂原子间断并可以任选被卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基单-至三取代。
Y1和Y2与它们所连的碳原子一起优选代表C3-C6-环烷基。
Z优选代表氢,代表各自任选被氟和/或氯取代的C1-C8-烷基、氰基-C1-C6-烷基、C3-C8-链烯基、C3-C8-炔基、C3-C8-环烷基、C3-C8-环烷基-C1-C2-烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-卤代烷氧基-C1-C4-烷基,代表苯氧基-C1-C4-烷基、苯基-C1-C4-烷氧基-C1-C4-烷基、苯硫基-C1-C4-烷基、苯基-C1-C4-烷硫基-C1-C4-烷基、苯基、苯基-C1-C4-烷基、五-或六元杂芳基、五-或六元杂芳基-C1-C4-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基单-至四取代,或代表下列基团:
或氰基。
p优选代表0-2。
l优选代表0-2。
R1优选代表氢(但在基团-CO2R1和-SO2R1中不是),代表各自任选被氟和/或氯取代的C1-C10-烷基、C2-C10-链烯基、C3-C6-炔基,代表各自任选被氟、氯、C1-C4-烷基、C1-C4-烷氧基取代的C3-C8-环烷基或C5-C8-环烯基,其中任选地一个亚甲基可以被氧或硫替代,或代表苯基、吡啶基、噻吩基、嘧啶基、噻唑基、苯基-C1-C4-烷基、吡啶基-C1-C2-烷基、噻唑基-C1-C2-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基单-至四取代。
R2优选代表氢,代表各自任选被氟和/或氯取代的C1-C6-烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C3-C6-链烯基氧基或代表苯基、苯基-C1-C4-烷基或苯基-C1-C4-烷氧基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基单-至四取代。
R1和R2此外与它们所连的氮原子一起可以优选代表各自任选被C1-C4-烷基取代的5-至8-元环,其中任选地一个亚甲基可以被氧或硫替代。
R3优选代表氢、任选被卤素取代的C1-C6-烷基或代表苯基或苯基-C1-C2-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基单-至四取代。
R4优选代表氢或C1-C6-烷基。
R5和R6各自独立地优选代表氢或任选被氟和/或氯取代的C1-C4-烷基。
R7优选代表各自任选被氟和/或氯取代的C1-C10烷基、C2-C10-链烯基、C3-C10-炔基、C1-C10-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷硫基-C1-C4-烷基,代表各自任选被氟、氯、C1-C4-烷基和/或C1-C4-烷氧基取代的C3-C8-环烷基或C3-C8-环烷氧基,其中任选地一个亚甲基可以被氧或硫替代,或代表苯基、苯氧基、苄氧基、五-或六元杂芳基或苯基-C1-C4-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基单-至四取代,或对于在Ar下所述的基团a)和c)的情况,也代表基团:
或对于基团g),也代表羟基。
R8优选代表氢或C1-C4-烷基。
R9优选代表氢、各自任选被氟和/或氯取代的C1-C10-烷基、C3-C8-链烯基、C3-C8-炔基、C1-C10-烷氧基、C3-C8-链烯基氧基,任选被氟、氯、C1-C4-烷基或C1-C4-烷氧基取代的C3-C8-环烷基,其中任选地一个亚甲基可以被氧或硫替代,或代表苯基、苯基-C1-C4-烷基或苯基-C1-C2-烷氧基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基单-至四取代。
R10优选代表氢、C1-C6-烷基或C3-C6-链烯基。
R9和R10此外与它们所连的氮原子一起可以优选代表任选被C1-C4-烷基取代的5-至8-元环,其中任选地一个亚甲基可以被氧或硫替代。
m优选代表0-2。
n优选代表0-2。
K特别优选代表氧或硫。
Ar特别优选代表Ar1,该Ar1代表苯基、萘基、喹啉基、噻吩基、嘧啶基、呋喃基、噻唑基、苯并噻唑基、噁唑基、吡唑基或吡啶基,这些基团各自任选地被下列基团单-至三取代:氟、氯、溴、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C2-C4-卤代链烯基氧基、C1-C2-亚烷二氧基、C1-C2-卤代亚烷二氧基、卤代-C1-C2-烷硫基、卤代-C1-C2-烷基亚磺酰基、卤代-C1-C2-烷基磺酰基、羟基、巯基、硝基、氰基、氨基或下列基团:
或特别优选代表Ar2,该Ar2代表Ar1,该Ar1还被下列基团取代:
苯基、吡啶基、嘧啶基、噻吩基、呋喃基、噻唑基、四唑基、三唑基、苄基、苯基-C1-C2-烷基、苯基-C1-C2-烷基-S(O)p-、噻吩基-C1-C2-烷氧基、噻唑基-C1-C2-烷氧基、吡啶基-C1-C2-烷氧基、嘧啶基-C1-C2-烷氧基、噻唑基-C1-C2-烷基-S(O)p-、吡啶基-C1-C2-烷基-S(O)p-、苯氧基、苯基-S(O)p-、吡啶基氧基、嘧啶基氧基、噻唑基氧基、吡啶基-S(O)p-、嘧啶基-S(O)p-或噻唑基-S(O)p-,其中这些取代基本身各任选被氟、氯、溴、C1-C4-烷基、C2-C4-链烯基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基单-至三取代。
L特别优选代表氧或硫。
V特别优选代表氧或代表-S(O)n-或>N-W。
W特别优选代表氢,代表各自任选被氟和/或氯取代的C1-C6-烷基、
C3-C6-链烯基、C3-C6-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C2-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C2-C3-烷基,代表苯基、苯基-C1-C2-烷基、苯基-C1-C2-烷氧基、吡啶基、噻唑基、嘧啶基、噻吩基、吡啶基-C1-C2-烷基、嘧啶基-C1-C2-烷基、噻唑基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基单-至三取代,或代表下列各式基团:
-COR1;-CO2R1;-SO2R1;
或氰基。
X特别优选代表CN、
或
Y1和Y3相互独立地特别优选代表氢,任选地代表氟、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C2-烷基,代表苯基、噻吩基、吡啶基、噻唑基、嘧啶基、苯基-C1-C2-烷基、噻唑基甲基、吡啶基甲基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基单-至三取代,或代表下列基团:
Y2、Y4、Y6相互独立地特别优选代表氢或C1-C4-烷基。
Y5特别优选代表氢,代表任选被氟取代的C1-C4-烷基或代表任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基单-至三取代的苯基。
Y4和Y5此外与它们所连的碳原子一起特别优选代表5-或6-元饱和或不饱和的环,该环可以被选自N、O和S的杂原子间断并可以任选被氟、氯、溴、甲基、叔丁基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基单-或二取代。
Y1和Y2与它们所连的碳原子一起特别优选代表C4-C6-环烷基。
Z特别优选代表氢,代表各自任选被氟和/或氯取代的C1-C6-烷基、氰基-C1-C3-烷基、C3-C6-链烯基、C3-C8-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C2-烷基、C1-C4-烷氧基-C1-C2-烷基、C1-C4-卤代-C1-C2-烷基,代表苯氧基-C1-C2-烷基、苯基-C1-C2-烷氧基-C1-C2-烷基、苯硫基-C1-C2-烷基、苯基-C1-C2-烷硫基-C1-C2-烷基、苯基-C1-C2-烷基、苯基、吡啶基-C1-C2-烷基、噻唑基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基单-至三取代,或代表下列基团:
-CO2R1;
-SO2R1;-COR1;
或氰基。
p特别优选代表0-2。
R1特别优选代表氢(但在基团-CO2R1和-SO2R1中不是),代表各自任选被氟和/或氯取代的C1-C6-烷基、C3-C6-链烯基、C3-C4-炔基,代表各自任选被氟、氯、C1-C2-烷基、C1-C2-烷氧基取代的C3-C6-环烷基或代表苯基或苄基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基单-或二取代。
R2特别优选代表氢,代表各自任选被氟和/或氯取代的C1-C4-烷基、C3-C4-链烯基、C3-C4-炔基、C1-C4-烷氧基、C3-C4-链烯基氧基或代表苯基、苄基、苄氧基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基单-或二取代。
R1和R2此外与它们所连的氮原子一起可以特别优选代表任选被C1-C2-烷基取代的5-或6-元环,其中任选地一个亚甲基可以被氧替代。
R5特别优选代表氢、甲基或乙基。
R7特别优选代表各自任选被氟和/或氯取代的C1-C6-烷基、C2-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C1-C4-烷氧基-C1-C2-烷基、C1-C4-烷硫基-C1-C2-烷基,代表各自任选被氟、氯、C1-C2-烷基和/或C1-C2-烷氧基取代的C3-C6-环烷基或C3-C6-环烷氧基,其中任选地一个亚甲基可以被氧替代,代表苯基、苯氧基、苄氧基、噻吩基、呋喃基、吡啶基、嘧啶基、噻唑基、吡唑基或苯基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、硝基或氰基单-或二取代,或对于在Ar下所述的基团a)和c)的情况,也代表基团:
或对于基团g),也代表羟基。
R8特别优选代表氢。
R9特别优选代表氢,代表各自任选地被氟和/或氯取代的C1-C6-烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C3-C6-环烷基,其中任选地一个亚甲基可以被氧替代,或代表苯基或苯基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、硝基或氰基单-或二取代。
R10特别优选代表氢或C1-C4-烷基。
R9和R10此外与它们所连的氮原子一起可以特别优选代表任选被C1-C2-烷基取代的5-或6-元环,其中任选地一个亚甲基可以被氧替代。
m特别优选代表0或1。
n特别优选代表0-2。
K非常特别优选代表氧和硫。
Ar非常特别优选代表Ar1,该Ar1代表苯基、噻吩基、嘧啶基、呋喃基或吡啶基,这些基团各自任选地被下列基团单-至三取代:氟、氯、溴、甲基、乙基、丙基、异丙基、仲-、正-、异-或叔丁基、甲氧基、乙氧基、丙氧基、异丙氧基、仲-、正-、异-或叔丁氧基、烯丙基氧基、甲基烯丙基氧基、2-丁烯基氧基、炔丙基氧基、2-丁炔基氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、亚甲基二氧基、二氟亚甲基二氧基、四氟亚乙基二氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、羟基、巯基、硝基、氰基、氨基或被下列基团之一取代:
a)-L-CO-R7,
d)NHSO2R7,
或代表Ar2,该Ar2代表Ar1,该Ar1还被下列基团取代:苯基、吡啶基、噻吩基、四唑基、三唑基、苄氧基、苄硫基、噻唑基甲氧基、吡啶基甲氧基、嘧啶基甲氧基、噻唑基甲硫基、吡啶基甲硫基、苯氧基或苯硫基,其中这些取代基本身各任选被氟、氯、溴、甲基、乙基、正丙基、异丙基、仲-、正-、异-或叔丁基、甲氧基、乙氧基、异丙氧基、仲-、正-或叔丁氧基、三氟甲基、三氟甲氧基、硝基或氰基单-或二取代。
L非常特别优选代表氧或硫。
V非常特别优选代表氧或硫。
Y1和Y3相互独立地非常特别优选代表氢、甲基、乙基、丙基、异丙基、正-、仲-、异-或叔丁基,代表苯基或苄基,它们各任选被氟、氯、溴、甲基、甲氧基、三氟甲基、二氟甲氧基或三氟甲氧基单-至三取代。
Y2、Y4、Y6相互独立地非常特别优选代表氢、甲基或乙基。
Y5非常特别优选代表氢、甲基、乙基、丙基、异丙基或代表任选被氟、氯、溴、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基、异丙氧基、叔丁氧基、三氟甲基或三氟甲氧基单-或二取代的苯基。
Y4和Y5此外与它们所连的碳原子一起非常特别优选代表6-元不饱和的环,该环可以任选被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基单取代。
Y1和Y2此外与它们所连的碳原子一起非常特别优选代表环丁基。
Z非常特别优选代表氢、甲基、乙基、烯丙基、炔丙基、环丙基、环戊基、环己基、环丙基甲基、环戊基甲基、环己基甲基、甲氧基甲基、乙氧基甲基,代表苯基、苄基、吡啶基甲基、噻唑基甲基,它们各任选被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基、硝基或氰基单-至二取代,或代表下列基团:
或氰基。
R1非常特别优选代表氢(但在基团-CO2R1和-SO2R1中不是)、甲基、乙基、丙基、异丙基、正-、异-、仲-或叔丁基、烯丙基、炔丙基、环丙基、环戊基、环己基,代表苯基或苄基,它们各任选被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、硝基或氰基单-或二取代。
R2非常特别优选代表氢、甲基、乙基、丙基、异丙基、烯丙基、炔丙基、甲氧基、乙氧基、烯丙基氧基或代表苄氧基,该基团任选被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、硝基或氰基单-至二取代。
R1和R2与它们所连的氮原子一起非常特别优选代表吡咯烷基、噻嗪基、哌啶基或吗啉基。
R5非常特别优选代表氢、甲基或乙基。
R7非常特别优选代表甲基、乙基、丙基、异丙基、正-、异-、仲-或叔丁基、乙烯基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、正-、异-、仲-或叔丁氧基、环丙基、环戊基、环己基、环戊基氧基、环己基氧基,代表苯基、吡啶基或苄基,它们各任选被氟、氯、溴、甲基、正-、异-、仲-或叔丁基、甲氧基、三氟甲基、三氟甲氧基、硝基或氰基单-或二取代,或对于在Ar下所述的基团
a)和c)的情况,也代表基团:
或对于基团g),也代表羟基。
R9非常特别优选代表氢、甲基、乙基、丙基、异丙基、正-、异-、仲-或叔丁基、环丙基、环戊基、环己基,代表苯基,该基团任选被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、硝基或氰基单-或二取代。
R10非常特别优选代表氢、甲基或乙基。
R9和R10与它们所连的氮原子一起非常特别优选代表吡咯烷基、哌啶基或吗啉基。
m非常特别优选代表1。
Ar尤其优选代表Ar1,该Ar1代表苯基、噻吩基、嘧啶基或吡啶基,这些基团各自任选地被下列基团单-至三取代:氟、氯、溴、甲基、乙基、丙基、异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、丙氧基、异丙氧基、正-、异-、仲-或叔丁氧基、烯丙基氧基、甲基烯丙基氧基、2-丁烯基氧基、炔丙基氧基、2-丁炔基氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、亚甲基二氧基、二氟亚甲基二氧基、四氟亚乙基二氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、羟基、硝基、巯基、氰基、氨基,或
代表Ar2,该Ar2代表Ar1,该Ar1还被下列基团取代:苯基、苄氧基或苯氧基,其中这些取代基本身各任选被氟、氯、溴、甲基、乙基、异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、异丙氧基、正-、仲-、异-或叔丁氧基、三氟甲基、三氟甲氧基、硝基或氰基单-或二取代。
K尤其优选代表氧或硫。
V尤其优选代表氧或硫。
X尤其优选代表CN。
Y1和Y3相互独立地尤其优选代表氢、甲基、乙基或丙基。
Z尤其优选代表氢或甲基。
Y2、Y4、Y5、Y6相互独立地尤其优选代表氢、甲基或乙基。
上面所列的所有的式(I)化合物均可以以顺式和反式异构体存在。为了简化表述,在每种情况下在用各式描述的化合物中仅示出一种异构体。然而,本发明也涉及其它各异构体。
上述一般的或优选的基团定义不仅适用于式(I)的终产物而且相应地适用于在每种情况下制备所需的原料和中间体。这些基团定义可以视需要相互组合,即包括给定的优选范围间的组合。
本发明优选的是含有上述作为优选(优选的)列出的意义组合的的式(I)化合物。
本发明特别优选的是含有上述作为特别优选(特别优选的)列出的意义组合的的式(I)化合物。
本发明非常特别优选的是含有上述作为非常特别优选(非常特别优选的)列出的意义组合的的式(I)化合物。
本发明尤其优选的是含有上述作为尤其优选(尤其优选的)列出的意义组合的的式(I)化合物。
饱和或不饱和的烃基,如烷基或链烯基,只要有可能,各就可以是直链或支链的,也包括它们与杂原子连接时,例如在烷氧基或烷硫基中时的情况。
除非另有指明,任选被取代的基团可以是单-或多取代的,并且在多取代的情况下,取代基可以相同或不同。
现已发现,通式(I)的新化合物可以通过下述方法获得:
(A)任选地在稀释剂存在下,任选地在碱或酸和/或式(IIIa)的金属化合物存在下,
Me(Q)2 (IIIa)
其中,
Me代表二价过渡金属原子,特别是镍,和
Q代表螯合物配体,特别是二齿螯合物配体,例如乙酰丙酮化物,
使式(II)化合物与式(III)化合物反应,得到了式(I)化合物,
其中
Ar和X如上所定义,
其中
V、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
A代表O或S(O)q,其中q代表0或2,
R11代表烷基,特别是C1-C6烷基,或苄基,
其中
Ar、V、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
K代表氧,
Z代表氢。
(R.G.Glushkov等人,Khim.-Farm.Zh.24,(7),(1990),24-27;M.V.Mezentseva等人,Khim.-Farm.Zh.25,(12),(1991),19-23;G.Dannhardt,A.Bauer,Pharmazie 51,(1996),805-810),
(B)此外,现已发现,下列式(I)化合物可以如下获得:
其中,
Ar、V、Y1、Y2、Y3、Y4、Y5、Y6、X和m如上所定义,和
K代表氧,
Z代表氢,
任选地在稀释剂存在下,使式(IV)化合物与式(V)化合物反应,得到了式(VI)化合物,
其中
Ar和X如上所定义,和
Hal表卤素,特别是氯或溴,
其中
V、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,
其中
V、Ar、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,
任选地在碱存在下和任选地在三价磷化合物(例如三苯基膦、亚磷酸三乙酯)存在下使式(VI)化合物进一步反应消除硫和卤化氢,得到式(I)化合物,其中Ar、V、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,K代表氧,和Z代表氢。
(参见A.Eschenmoser等人,Helv.Chim.Acta 54,(1971),710-734;V.Issartel等人,C.R.Acad.Sci.,Ser.II,Mec.,Phys.,Chim.,Astron.321,(12),(1995),521-524)。
(C)此外,现已发现,下列式(I)化合物可以如下获得:
其中,
Ar、V、Z、X、Y1、Y2、Y3、Y4、Y5、Y6和m和n具有上面给出的意义之一,和
K代表氧,但
Z不代表氢,
任选地在稀释剂存在下,使式(VII)化合物与卤化剂如光气、二光气和三光气反应,得到了式(VIII)化合物,
其中
V、Z、Y1、Y2、Y3、Y4、Y5、Y6和m具有上面给出的意义之一,和Z不代表氢,和
其中
V、Z、Y1、Y2、Y3、Y4、Y5、Y6和m具有上面给出的意义之一,和Z不代表氢,和
Hal代表卤素,特别是氯或溴,
然后,任选地在稀释剂存在下和任选地在酸接受体存在下使式(VIII)化合物与式(II)化合物反应,
其中
Ar和X如上所定义,
(参见G.Dannhardt,A.Bauer,Pharmazie 51,(1996),805-810)。
(D)任选地在溶剂存在下和任选地在碱存在下,使式(Ia)化合物与式(IX)的烷基化剂、酰化剂、磺酰化剂或缩合剂反应,得到了式(I)化合物,
其中
Ar、V、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和K代表氧,
Z-G (IX)
其中
G是离去基团如卤素(特别是碘、溴、氯),磺酸酯(如甲磺酸酯、三氟甲磺酸酯或甲苯磺酸酯)或烷氧基,
其中
Ar、V、Z、X、Y1、Y2、Y3、Y4、Y5、Y6和m具有上面给出的意义之一,和
K代表氧,但
Z不代表氢。
(E)在溶剂存在下,任选地在碱和贵金属配合物、优选钯配合物存在下,使式(I1)化合物与式(X)的硼酸反应,得到了式(I2)化合物,
其中
Ar1、V、X、Y1、Y2、Y3、Y4、Y6、Z和m如上所定义,和
Hal代表卤素,特别是溴,
Ar2-B(OH)2 (X)
其中
Ar2’代表上面在Ar2下作为Ar1的另外的取代基提到的取代基,
其中
Ar2、V、X、Y1.Y2、Y3、Y4、Y5、Y6、Z和m如上所定义,和
K代表氧。
(F)此外发现,在溶剂存在下,在硫化剂如五硫化二磷或2,4-二(4-甲氧基苯基)-1,2,3,4-二硫杂phosphetane-2,4-二硫化物(Lawesson氏试剂)存在下,使下列式(I)化合物反应,
其中
Ar、Z、V、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
K代表氧,
得到了下列式(I)化合物,
其中
Ar、Z、V、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
K代表硫。
(G)此外发现,在过酸(如过乙酸或间氯过苯甲酸)或过氧化氢存在下,在钼酸盐或钨酸盐(如钼酸铵或钨酸钠)存在下,氧化下列式(I)化合物,
其中
Ar、K、Z、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
V代表硫原子,
得到了式(I3)化合物,
其中
Ar、K、X、Z、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
n代表1和2。
根据方法A,使用例如4-甲基-苯甲酰基乙腈和2-甲氧基-2-二氢吗啉作为原料,该反应过程可以用下式表示:
根据方法B,使用例如2-溴-2-(3-氯苯甲酰基)乙腈和吗啉-3-硫酮作为原料,该反应过程可以用下式表示:
根据方法C,使用例如3,4-二氯苯甲酰基乙腈和N-甲基吗啉-3-酮作为原料,该反应过程可以用下式表示:
根据方法D,使用例如3-(4-三氟甲氧基-苯基)-2-(1,4-噁嗪烷-3-亚基)-3-氧代丙腈和2-氯-5-氯甲基吡啶作为原料,该反应过程可以用下式表示:
根据方法D,使用例如3-(4-三氟甲基-苯基)-2-(1,4-噁嗪烷-3-亚基)-3-氧代丙腈和4-氯苯甲酰氯作为原料,该反应过程可以用下式表示:
根据方法E,使用例如3-(4-溴苯基)-2-(1,4-噁嗪烷-3-亚基)-3-氧代丙腈和4-氯苯基硼酸作为原料,该反应过程可以用下式表示:
根据方法F,使用例如3-(4-氯苯基)-2-(1,4-噁嗪烷-3-亚基)-3-氧代丙腈和Lawesson氏试剂作为原料,该反应过程可以用下式表示:
根据方法G,使用例如3-(3,4-二氯苯基)-2-(1,4-噻嗪烷-3-亚基)-3-氧代丙腈和两当量的间氯过苯甲酸(MCPBA)作为原料,该反应过程可以用下式表示:
作为方法A的原料需要的一些式(II)化合物是新的,并可以通过原则上从文献中已知的方法(Organikum,16th修订版,pp415,417,VEBDeutscher Verlag der Wissenschaften,Berlin 1986)制备,
其中,
Ar和X如上所定义。
式(II)化合物中,下列式(II)化合物特别适合于制备新的农药、特别是杀螨、除草和杀虫的终产物:
式(II-1-b)化合物:
其中
T如下表中所定义:
化合物编号 | T | m.p.℃ |
II-1-b-1 | 3-Cl,4-F | 78 |
II-1-b-2 | 4-Cl,3-F | 87 |
II-1-b-3 | 3,5-(CF3)2 | 91 |
II-1-b-4 | 2,4-Cl2,5-F | 106 |
II-1-b-5 | 3,5-Cl2,4-F | 138-140 |
II-1-b-6 | 4-Cl,2-F | 90-94 |
II-1-b-7 | 3-CF3,5-CH3 | 92 |
II-1-b-8 | 3-Cl,4,5-F2 | 84-88 |
II-1-b-9 | 4-CN,2,5-F2 | 107-108 |
II-1-b-10 | 2,3-F2 | 74 |
II-1-b-11 | 3-F,4-CF3 | 92 |
II-1-b-12 | 3,4-O-CF2-O | 70-73 |
II-1-b-13 | 3-NO2,5-CF3 | |
II-1-b-14 | 4-Cl,2,5-F2 | 116 |
II-1-b-15 | 3,4,5-(OC2H5)3 | 122 |
II-1-b-16 | 4-Br,2-F | 118 |
II-1-b-17 | 2,6-Cl2,4-CF3 | 123 |
II-1-b-18 | 2-F,4-NO2 | 168 |
II-1-b-19 | 2,4-Cl2,5-NO2 | 100 |
II-1-b-20 | 4-Cl,2-F,5-NO2 | 118 |
化合物编号 | T | m.p.℃ |
II-1-b-21 | 2,4-F2,5-NO2 | 128 |
II-1-b-22 | 4-Br,2-F,5-NO2 | 141 |
II-1-b-23 | 2-F,4-CF3 | 62 |
II-1-b-24 | 4-OCF3,3-NO2 | 95 |
II-1-b-25 | 4-Cl,2-NO2 | 130 |
II-1-b-26 | 2-F,3-CF3 | 67-69 |
II-1-b-27 | 2-Cl,6-F | 46-48 |
II-1-b-28 | 2-Cl,3-CF3 | 90-93 |
II-1-b-29 | 3,4-O-(CF2)2-O- | 206 |
II-1-b-30 | 2-Cl,4-SCH3 | 110 |
II-1-b-31 | 2-Cl,4-SO2CH3 | 202 |
式(II-2-b)化合物:
其中
T如下表中所定义:
化合物编号 | T | m.p.℃ |
II-2-b-1 | 2,6-Cl2 | >220 |
II-2-b-2 | 2,6-Cl2,4-CH3 | 95 |
II-2-b-3 | 6-Cl | 122 |
式(II-3-b)化合物:
其中
T如下表中所定义:
化合物编号 | T | m.p.℃ |
II-3-b-1 | 2-CF3,3-(4-Cl′-C6H4) | 油状物 |
II-3-b-2 | 2-CF3,3-(2,4-Cl2′-C6H3) | 油状物 |
第II-4-b-1号化合物:
化合物II-4-b-1;m.p.241℃
和
第II-5-b-1号化合物:
化合物II-5-b-1,树脂状
式II-1-b至II-5-b化合物形成了早先的、但尚未公开的专利申请的部分主题。
式(II)化合物例如如下获得:在酸(例如无机酸如盐酸)或碱(例如碱金属氢氧化物如氢氧化钠或氢氧化钾)存在下和任选地在稀释剂(例如含水醇如甲醇或乙醇)存在下在0-200℃、优选20-150℃下水解式(XI)化合物,然后脱羧,
其中
Ar如上所定义,
R12代表烷基,特别是C1-C6-烷基,或苄基,其可以是任选地被取代的。
式(XI)化合物可以通过已知方法(Organikum,16th修订版,pp480,VEB Deutscher Verlagder Wissenschaften,Berlin 1986)制备。
式(XI)化合物例如通过下述方法获得:在碱(例如金属醇化物如甲醇钠或乙醇钠)存在下和任选地在稀释剂(例如乙醚或由醇盐衍生的醇)存在下在0-150℃、优选20-120℃下使式(XII)化合物与式(XIII)的氰基乙酸酯反应,
其中
Ar如上所定义,
其中
R12代表烷基,特别是C1-C6-烷基。
一些式(XII)化合物是新的,可以通过原则上已知的方法(例如Organikum,16th 修订版,pp423,VEB Deutscher Verlag derWissenschaften,Berlin 1986)制备。
式(XII)化合物例如通过下述方法获得:任选地在稀释剂(例如任选地氯代的脂族或芳族烃如甲苯或二氯甲烷)存在下在0-150℃、优选20-100℃下使式(XIV)化合物与卤化剂(例如亚硫酰氯、光气、三氯化磷)反应,
其中
Ar如上所定义。
式(XIII)的氰基乙酸酯是有机化学中的已知化合物。
作为方法A的原料也需要的式(III)化合物
其中
V、Y1、Y2、Y3、Y4、Y5、Y6、R11和m如上所定义,和
A代表氧,
可以通过已知方法(J.Krsi,P.Berensci,Chem.Ber.,101,1979(1968))制备。
式(III)化合物例如通过如下方法获得:在-20至150℃、优选0-100℃下使式(VII)化合物与烷基化剂(例如硫酸二甲酯、四氟硼酸三乙基氧鎓盐(Meerwein盐))反应,
其中
V、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
Z代表氢。
此外,用作方法A原料需要的式(III)化合物,
其中
V、Y1、Y2、Y3、Y4、Y5、Y6、R11和m如上所定义,和
A代表硫,
如下获得:在溶剂存在下,用硫化剂如Lawesson氏试剂先将式(VII)
化合物转化成式(V)的硫代酰胺,
其中
V、Z、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,和
Z代表氢,
其中
V、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义,
然后,任选地在碱存在下和在溶剂存在下与式(XV)的烷基化剂反应,
R11-Hal (XV)
其中
A11如上所定义,和
Hal代表卤素,特别是碘或溴。
方法A的特征在于使其中Ar和X如上所定义的式(II)化合物与其中R11、V、W、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义的式(III)化合物在稀释剂存在下和任选地在碱存在下相互反应。
对于方法A来说合适的稀释剂是所有对反应参与者呈惰性的有机溶剂。优选使用任选被氯代的脂族或芳族烃如甲苯、二甲苯、1,2-二氯苯、氯仿或二氯甲烷,还有极性溶剂如二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺或N-甲基吡咯烷酮。
也可使用的溶剂是醚类如乙醚、甲基叔丁基醚、四氢呋喃或二噁烷,以及还有腈类如乙腈,和酯类如乙酸乙酯、,此外还有酮类如丙酮或异丙基甲基酮。
合适的用于进行方法A的碱是所有常规的不水解反应参与者的酸接受体。
优选使用叔胺如二氮双杂环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、三乙胺、吡啶或N,N-二甲基苯胺。
也可以使用醇盐如甲醇钠、乙醇钠、乙醇镁、叔丁醇钾,以及金属氢化物如氢化钠、氢化钙、,以及还有碱金属或碱土金属碳酸盐或碳酸氢盐如碳酸氢钠、碳酸钾或碳酸钠。
对于进行方法A来说合适的酸是所有的不水解反应参与者的酸。优选使用有机酸如对甲苯磺酸和三氟乙酸。
当进行方法A时,反应温度可以在较宽的范围内变化。有利地,反应在-20至160℃、优选0-120℃的温度下进行。
方法A优选在常压下进行。
当进行方法A时,基于式(II)的反应组分,式(III)的反应组分以等摩尔量或较大过量(最多5mol)、优选1.5-2倍摩尔量使用。
任选使用的碱优选以与式(II)的反应组分等摩尔的量使用。任选使用的酸优选以催化量使用。
方法B的特征在于使式(IV)化合物各与式(V)的硫代酰胺任选地在稀释剂存在下和任选地在酸结合剂存在下反应。
式(IV)的原料可以通过已知方法(Sequin,Vieles,BSCFAS,Bull.Soc.Chim.Fr.(1956)1210,1211;Bushey,Hoover,J.Org.Chem.,45,4198(1980))制备。式(V)化合物可以在惰性溶剂如甲苯中从相应的烯酮化合物用亚硫酰化试剂、特别是P2S5和Lawesson氏试剂制备(参见制备实施例4)。
对于方法B来说合适的稀释剂是所有的对式(IV)化合物呈惰性的溶剂。优选使用烃类如轻质汽油、苯、甲苯、二甲苯和四氢萘,此外还有卤代烃类如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,还有酮类如丙酮和甲基异丙基酮,此外还有醚类如乙醚、四氢呋喃和二噁烷,还有羧酸酯类如乙酸乙酯,以及还有强极性溶剂如二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜和环丁砜。
合适的用于本发明方法B反应的酸结合剂是所有常规的酸接受体。优选使用叔胺如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,聚合碱如二异丙基氨基聚苯乙烯,还有碱土金属氧化物如氧化镁和氧化钙,此外还有碱金属和碱土金属碳酸盐如碳酸钠、碳酸钾和碳酸钙,以及还有碱金属氢氧化物如氢氧化钠和氢氧化钾。
合适的用于本发明方法B的磷试剂是亚磷酸烷基酯如亚磷酸三乙酯、亚磷酸三丁酯或三苯基膦类如三苯基膦。
当进行方法B时,反应温度可以在较宽的范围内变化。一般,反应在0-200℃、优选-20-150℃的温度下进行。
当进行方法B时,式(IV)的原料和式(V)的硫代酰胺一般各以大约等摩尔量使用。然而,也可以使用较大过量的一种或另一种组分。后处理通过常规方法进行。
方法C的特征在于使式(VII)化合物与卤化剂如光气、二光气、三光气,任选地在稀释剂存在下反应,得到式(VIII)化合物,然后该化合物与式(II)化合物任选地在酸结合剂存在下和任选地在稀释剂存在下反应。式(VII)原料可以通过例如Bushey,Hoover,J.Org.Chem.45,4198(1980)所述的方法制备。
合适的用于本发明方法C反应的酸结合剂是所有常规的酸接受体。优选使用叔胺如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,聚合碱如二异丙基氨基聚苯乙烯,此外还有碱土金属氧化物如氧化镁和氧化钙,还有碱金属和碱土金属碳酸盐如碳酸钠、碳酸钾和碳酸钙,以及还有碱金属氢氧化物如氢氧化钠和氢氧化钾。
对于方法C来说合适的稀释剂是所有的对卤化剂呈惰性的溶剂。优选使用烃类如轻质汽油、苯、甲苯、二甲苯和四氢萘,此外还有卤代烃类如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,还有酮类如丙酮和甲基异丙基酮,此外还有醚类如乙醚、四氢呋喃和二噁烷,还有羧酸酯类如乙酸乙酯,还有腈类如乙腈,以及还有强极性溶剂如二甲基亚砜和环丁砜。
当进行方法C时,反应温度可以在较宽的范围内变化。通常,反应在-20至100℃、优选0-80℃的温度下进行。
方法C一般在常压下进行。
当进行方法C时,式(VII)的原料和相应的卤化剂一般各以大约等摩尔量使用。然而,也可以使用较大过量(最多3mol)的一种或另一种组分。后处理通过常规方法进行。通常,除去沉淀的盐,剩下的反应混合物通过在减压下除去稀释剂而被浓缩。
方法D的特征在于其中Ar、V、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义、K代表氧和Z代表氢的式(I)化合物各与式(IX)的烷基化剂、酰化剂、磺酰化剂或缩合剂任选地在稀释剂存在下和任选地在酸结合剂存在下反应。
所用的式(IX)的烷基化剂、酰化剂、磺酰化剂或缩合剂是已知的用于有机化学合成中的化学品。
对于方法D来说合适的稀释剂是所有的对上述试剂呈惰性的溶剂。优选使用烃类如轻质汽油、苯、甲苯、二甲苯和四氢萘,此外还有卤代烃类如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,还有酮类如丙酮和甲基异丙基酮,此外还有醚类如乙醚、四氢呋喃和二噁烷,还有羧酸酯类如乙酸乙酯,以及还有强极性溶剂如二甲基亚砜、二甲基甲酰胺、N-甲基吡咯烷酮和环丁砜。如果酰化剂和磺酰化剂的水解稳定性允许,反应也可以在水存在下进行。
合适的用于本发明方法D反应的酸结合剂是所有常规的酸接受体。优选使用叔胺如三乙胺、吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,此外还有碱土金属氧化物如氧化镁和氧化钙,还有碱金属和碱土金属碳酸盐如碳酸钠、碳酸钾和碳酸钙,以及还有碱金属氢氧化物如氢氧化钠和氢氧化钾,还有碱金属氢化物如氢化钠、氢化钾或碱金属醇盐如叔丁醇钾。
当进行方法D时,反应温度可以在较宽的范围内变化。通常,反应在-70至+150℃、优选-20至100℃的温度下进行。
当进行方法D时,上述式(I)的原料和上述式(IX)的试剂一般各以大约等摩尔量使用。然而,也可以使用较大过量(最多5mol)的上述试剂。后处理通过常规方法进行。
用于进行方法E的优选的催化剂是钯(O)配合物。优选例如四(三苯基膦)钯。
进行方法E所需要的一些芳基硼酸是市售的,例如4-氯苯基硼酸,或它们可以通过已知方法制备。
用于进行方法E的合适的酸接受体是无机或有机碱。它们优选包括碱土金属或碱金属的氢氧化物、乙酸盐、碳酸盐或碳酸氢盐,如氢氧化钠、氢氧化钾、氢氧化钡或氢氧化铵、乙酸钠、乙酸钾、乙酸钙或乙酸铵、碳酸钠、碳酸钾或碳酸铵、碳酸氢钠或碳酸氢钾,碱金属氟化物如氟化铯,以及还有叔胺如如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一碳烯(DBU)。
用于进行本发明方法E的合适的稀释剂是水、有机溶剂和其任何混合物。可以提及的例子是脂肪族、脂环族或芳族的烃类,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或四氢萘;卤代烃类,如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷、三氯乙烷或四氯乙烯;醚类,如乙醚、异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二甘醇二甲基醚或苯甲醚;醇类,如甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔丁醇、乙二醇、丙-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二甘醇单甲基醚、二甘醇单乙基醚;水。
当进行方法E时,反应温度可以在较宽的范围内变化。通常,反应在0-140℃、优选50-100℃的温度下进行。
当进行方法E时,其中Ar2’如上所定义的式(X)硼酸和其中Ar1、K、V、X、Y1、Y2、Y3、Y4、Y5、Y6、Z、m和Hal如上所定义的式(I1)化合物以1∶1-3∶1、优选1∶1-2∶1的摩尔比使用。催化剂一般以每摩尔式(I1)化合物用0.005-0.5摩尔、优选0.01-0.1摩尔的量使用。碱一般过量使用。
方法F的特征在于使其中Ar、V、X、Y1、Y2、Y3、Y4、Y5、Y6、Z和m如上所定义和K代表氧的式(I)化合物与硫化剂任选地在稀释剂存在下反应。
所用的硫化剂是已知的用于合成的化学品,例如五硫化二磷或2,4-二-(4-甲氧基苯基)-1,2,3,4-二硫杂phosphetane-2,4-二硫化物(Lawesson氏试剂)。
对于方法F来说合适的稀释剂是所有的对上述试剂呈惰性的溶剂。优选使用烃类如轻质汽油、苯、甲苯、二甲苯和四氢萘,此外还有卤代烃类如二氯甲烷、氯仿、氯苯和邻二氯苯,醚类如四氢呋喃、二噁烷、异丙醚或甲基叔丁基醚。
当进行方法F时,反应温度可以在较宽的范围内变化。通常,反应在0-250℃、优选40-200℃的温度下进行。
当进行方法F时,式(I)的原料和上述试剂一般各以大约等摩尔量使用。然而,也可以使用较大过量(最多5mol)的上述试剂。后处理通过常规方法进行。
方法G的特征在于使其中Ar、K、X、Y1、Y2、Y3、Y4、Y5、Y6和m如上所定义和V代表硫原子式(I)化合物与氧化剂如过乙酸、过丙酸、过邻苯二甲酸、间氯过苯甲酸或过氧化氢在钼酸盐或钨酸盐存在下在对所述氧化剂呈惰性的稀释剂存在下反应。
用于本发明方法G的优选的稀释剂是卤代烃类如二氯甲烷、氯仿、氯苯和邻二氯苯,还有羧酸酯类如乙酸乙酯,或强极性溶剂如二甲基亚砜和环丁砜。
当进行方法G时,反应温度可以在较宽的范围内变化。通常,反应在-30至100℃、优选-10至80℃的温度下进行。
当进行方法G时,式(I)原料和所述的氧化剂一般以1∶1或1∶2的摩尔比使用。然而,也可以使用较大过量(最多5mol)的一种或另一种组分。后处理通过常规方法进行。
本发明方法G一般在常压下进行。
本发明活性化合物特别适于用作脱叶剂、干燥剂、杀茎杆剂和尤其是用作除草剂。所谓的杂草,就其最广义而言,应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。
对于防治杂草来说所需要的本发明活性化合物的剂量为0.001-10kg/ha,优选0.005-5kg/ha。
本发明化合物可以与例如下列植物相关使用:
下列属的双子叶杂草:苘麻属、苋属、豚草属、Anoda、春黄菊属、Aphanes、滨藜属、雏菊属、鬼针草属、荠属、飞廉属、决明属、矢车菊属、藜属、蓟属、旋花属、曼陀罗属、山马蝗属、刺酸模属、糖芥属、大戟属、鼬瓣花属、牛膝菊属、猪殃殃属、木槿属、番薯属、地肤属、野芝麻属、独行草属、母草属、母菊属、薄荷属、山靛属、Mullugo、勿忘我属、罂粟属、牵牛属、车前属、蓼属、马齿苋属、毛莨属、萝卜属、蔊菜属、节节菜属、酸模属、猪毛菜属、千里光属、田菁属、黄花稔属、芥属、茄属、苦苣菜属、尖瓣花属、繁缕属、蒲公英属、遏蓝菜属、三叶草属、荨麻属、婆婆纳属、堇菜属、苍耳属。
下列属的双子叶作物:花生属、甜菜属、芸苔属、黄瓜属、南瓜属、向日葵属、胡萝卜属、大豆属、棉属、番薯属、莴苣属、亚麻属、番茄属、烟草属、菜豆属、豌豆属、茄属、巢菜属。
下列属的单子叶杂草:山羊草属、冰草属、翦股颖属、看麦娘属、Apera、燕麦属、臂形草属、雀麦属、栗草属、鸭跖草属、狗牙根属、莎草属、龙爪茅属、马唐属、稗属、荸荠属、蟋蟀草属、画眉草属、野黍属、羊茅属、飘拂草属、异蕊花属、白茅属、鸭嘴草属、千金子属、黑麦草属、雨久花属、黍属、雀稗属、
草属、梯牧草属、早熟禾属、筒轴茅属、慈姑属、莞草属、狗尾草属、高粱属。
下列属的单子叶作物:葱属、凤梨属、天门冬属、燕麦属、大麦属、稻属、黍属、蔗属、黑麦属、高粱属、黑小麦、小麦属、玉蜀黍属。
然而,本发明活性化合物的应用决不限于这些属,且也可以相同的方式延伸至其它植物。
根据本发明,可以处理所有植物和植物部分。这里,植物应理解为所有植物和植物群体如希望的或不希望的野生植物或作物(包括天然存在的作物)。作物可以是通过常规种植和最优化方法或通过生物技术和基因工程方法或这些方法的结合可以获得的植物,包括转基因植物,也包括植物变种,无论它们是否可以被植物品种保护权利机构保护。植物部分应被理解为意指植物的所有地上和地下部分和器官例如芽、叶、花和根,可提及的例子是叶、针叶、茎、树干、花、果体、果实和种子以及还有根、块茎和根茎。植物部分也包括收割物,以及有生长力的和有生殖能力的繁殖材料例如秧苗、块茎、根茎、切割物和种子。
根据本发明用活性化合物对植物或植物部分的处理按照常规的处理方法例如浸蘸、喷雾、蒸发、雾化、撒播、刷涂和在繁殖材料的情况下特别是种子的情况下还可以通过单-或多层涂布直接地或通过作用于它们的环境、栖生地或储存地来进行。
取决于化合物的浓度,化合物适合于灭生性防治杂草,例如工业地域和铁道线,以及有或无种植树林的道路和广场。同样,化合物可以用于防治多年生作物中的杂草,例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明的活性化合物非常适合于以芽前和芽后二种方式选择性地防治双子叶作物中的单子叶杂草。它们可非常成功地用于例如防治棉花或甜菜中的有害杂草。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
这些制剂可以用已知的方式生产,例如,将活性化合物与扩充剂,即液体和/或与固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
在用水作扩充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份、矿物和植物油,醇类,如丁醇或二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐,适合用于颗粒剂的固体载体有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可能使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%,以及优选含有扩充剂和/或表面活性剂。
本发明活性化合物可以其商业上可行的制剂和由这些制剂制备的使用形式作为与如下的其它活性化合物的混合物存在:杀虫剂、引诱剂、不育剂、杀细剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯类、羧酸酯类、氯代烃类、苯基脲类、由微生物产生的物质,及其它。在本发明的优选实施方案中,也可以将安全剂与本发明化合物混合以增加作物的相容性。
特别有利的混合组分的例子如下:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacryl-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvone,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,epoxiconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫代氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,
quinconazole,五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸异丙酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘代甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-N-碳酰苯胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫代氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴代甲基)戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫代氰酰甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈),
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑啉基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-硫代苯二羧酸酯,
顺-1-(4-氯代苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉]盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑啉基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲烷亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸钠盐,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫代氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,Acetamiprid,氟酯菊酯,棉铃威,涕灭威,氧涕灭威,甲体氯氰菊酯(Alpha-cypermethrin,Alphamethrin),双虫脒,avermectin,AZ60541,azadirachtin,甲基吡噁磷,azinphos-A,保棉磷,三唑锡,
日本甲虫芽孢杆菌(Bacillus popilliae),球形芽孢杆菌(Bacillus sphaericus),枯草芽孢杆菌(Bacillus subtilis),苏云金芽孢杆菌(Bacillus thuringiensis),Baculoviren,蚕白僵菌(Beauveria bassiana),纤细白僵菌(Beauveria tenella),噁虫威,丙硫克百威,杀虫磺,苯螨特,氟氯氰菊酯,Bifenazate,氟氯菊酯,Bioethanomethrin,生物氯菊酯,BPMC,溴硫磷A,合杀威,噻嗪酮,butathiofos,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫百克威,杀螟丹,除线威,氯氧磷,Chlorfenapyr,毒虫畏,氟啶脲,氯甲硫磷, 毒死蜱,甲基毒死蜱,Chlovaporthrin,顺式-苄呋菊酯,顺式氯菊酯,clocythrin,除线威,四螨嗪,杀螟腈,Cycloprene,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,敌敌畏,除虫脲,乐果,甲基毒虫畏,diofenolan,乙拌磷,docusat-sodium,dofenapyn,
克瘟散,emamectin,烯炔菊酯,硫丹,entomopfthora spp.,高氰戊菊酯,乙硫苯威,乙硫磷,灭线磷,etofenprox,醚菊酯,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,苯硫威,fenoxacrim,双氧威,氯氰菊酯,fenpyrad,fenpyrithrin,唑螨酯,氰戊菊酯,fipronil,氟定胺,fluazuron,flubrocythrinate,氟螨脲,氟氰戊菊酯,氟虫脲,Flutenzine,氟胺氰菊酯,地虫硫磷,丁苯硫磷,噻唑磷,fubfenprox,呋线威,
Granulosis viruses,
Halofenozide,HCH,庚烯磷,氟铃脲,噻螨酮,烯虫乙酯,
吡虫啉,氯唑磷,异丙胺磷,噁唑磷,ivermectin,
Nuclear polyhedrosis viruses,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,methamidophos,Metharhiziumanisopliae,Metharhizium flavoviride,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,
二溴磷,nitenpyram,Nithiazine,Novaluron,
氧乐果,杀线威,亚砜吸磷,
玫烟色拟青霉(Paecilomyces fumosoroseus),对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,嘧啶磷-A,嘧啶磷-M,丙溴磷,猛杀威,残杀威,丙硫磷,发果,pymetrozine,吡唑硫磷,pyresmethrin,除虫菊酯,哒螨酮,Pyridathion,pyrimidifen,蚊蝇醚,
喹硫磷,
Ribavirin,
蔬果磷,sebufos,silafluofen,spinosad,治螟硫磷,甲丙硫磷,
氟胺氰菊酯,tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,theta-cypermethrin,thiamethoxam,thiapronil,thiatriphos,thiocyclamhydrogen oxalate,硫双威,久效磷,thuringiensin,二甲硫吸磷,虫线磷,四溴菊酯,苯噻螨,三唑磷,triazuron,trichlophenidine,敌百虫,杀虫隆,混灭威,
芽灭多,vaniliprole,verticillium lecanii,
YI5302,
zeta-cypermethrin,zolaprofos,
环丙烷羧酸(1R-顺式)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)-亚呋喃基)-甲基]-2,2-二甲酯,
环丙烷羧酸(3-苯氧基苯基)-甲基-2,2,3,3-四甲酯,
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺,
2-(2-氯-6-氟代苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰氧基)-3-十二烷基-1,4-萘二酮,
2-氯-N-[[[4-(1-苯基乙氧基)苯基]-氨基]-羰基]-苯甲酰基,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)苯基]-氨基]-羰基]-苯甲酰基,
氨基甲酸3-甲基苯基丙酯,
4-[4-(4-乙氧基苯基)-4-甲基戊基]-1-氟-2-苯氧基-苯,
4-氯-2-(1,1-二甲基乙基)-5-[[2-(2,6-二甲基-4-苯氧基苯氧基)乙基]硫基]-3(2H)-哒嗪酮,
4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮,
4-氯-5-[(6-氯-3-吡啶基)甲氧基]-2-(3,4-二氯苯基)-3(2H)-哒嗪酮,
苏云金芽孢杆菌菌株EG-2348,
[2-苯甲酰基-1-(1,1-二甲基乙基)-苯甲酰肼,
丁酸2,2-二甲基-3-(2,4-二氯举基)-2-氧代-1-氧杂螺[4.5]十二烷-3-烯-4-酯,
[3-[(6-氯-3-吡啶基)甲基]-2-亚噻唑烷基]-氨腈,
二氢-2-(硝基亚甲基)-2H-1,3-噻嗪-3(4H)-甲醛,
[2-[[1,6-二氢-6-氧代-1-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯,
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸,
N-(4-氯苯基)-3-[4-(二氟甲氧基)苯基]-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺,
N-[(2-氯-5-噻唑基)甲基]-N′-甲基-N″-硝基-胍,
N-甲基-N′-(1-甲基-2-丙烯基)-1,2-肼二硫代二甲酰胺,
N-甲基-N′-2-丙烯基-1,2-肼二硫代二甲酰胺,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸酯。
除草剂:
乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、benzobicyclon、吡草酮、新燕灵(乙酯)、双丙氨酰磷、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butroxydim、丁草敌、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、草灭畏、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、cinidon(-ethyl)、环庚草醚、醚黄隆、clefoxydim、烯草酮、炔草酸、异噁草酮、氯甲酰草胺、二氯吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、cybutryne、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、吡氟草胺、diflufenzopyr、唑隆、哌草丹、二甲草胺、二甲丙乙净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、杀草隆、epoprodan、茵达灭、戊草丹、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵乙酯、fentrzamide、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、florasulam、吡氟禾草灵(丁酯)、fluazolate、flucarbazone、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、吡唑磺草胺、氟草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flurpyrsulfuron(-methyl、sodium)、芴丁酸、氟啶草酮、氯氟吡氧乙酸、氟嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamide、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、精吡氟氯禾灵(甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、imazapic、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘磺隆(甲酯,钠盐)、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草胺、isoxachlortole、isoxaflutole、噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻酰草胺、mesotrione、苯嗪草酮、吡唑草胺、甲基苯噻隆、吡喃隆、秀谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆(甲酯)、草达灭、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺乐灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、壬酸、二甲戊灵、pendralin、pentoxazone、甜菜宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、喔草酯、异丙草胺、戊炔草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆(乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭藻醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcitrione、甲磺草胺、嘧黄隆(甲酯)、草锍磷、甲嘧磺隆、牧草胺、特丁噻草隆、tepraloxydim、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻黄隆(甲酯)、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、灭草环、氟乐灵和氟胺黄隆。
此外,本发明活性化合物可以以其商业上可行的制剂和以由这些制剂制备的使用形式与增效剂的混合物存在。增效剂是可以增加活性化合物活性,而所添加的增效剂本身无需有活性的化合物。
由商业上可行的制剂制备的使用形式中的活性化合物的含量可以在相当宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
化合物是以适合于使用形式的常规方式施用的。
本发明化合物适于防治动物害虫,特别是农业,林业,储藏品保护和材料保护以及卫生领域所遇到的动物害虫,优选节肢动物和线虫类,尤其是昆虫和蛛形纲。它们对于一般敏感性和抗性物种都是有活性的,并且抗发育的所有阶段或部分阶段。上述害虫包括:
等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber。
多足纲目(Diplopoda),例如Blaniulus gutttulatus。
唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。
综合纲目(Symphyla),例如Scutigerella immaculata。
缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。
弹尾目(Collembola),例如Onychiurus armatus。
蠊目(Blattaria)和直翅目(Orthoptera),例如东方非蠊(Blattaorientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoria migratorioides),长额负蝗(Melanoplusdifferentialis)和Schistocerca gregaria。
革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia)。
等翅目(Isoptera),例如白蚁属(Reticulitermess pp.)。
虱目(Anoplura),例如葡萄根瘤蚜(Phylloxera vastatrix)、瘿绵蚜属(Pemphigu sspp.)、头虱(Pediculus humanus corporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.)。
食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalineaspp.。
缨翅目(Thysanoptera),例如西方花蓟(Frankliniellaoccidentalis)、温室条蓟马(Hercinothrips femoralis)、节瓜蓟马(Thrips palmi)和棉蓟马(Thrips tabaci)。
异翅亚目(Heteroptera),例如褐盾蝽属(Eurygaster spp.),Dysdercus intermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimexlectularius),Rhodnius prolixus和吸血猎蝽属(Triatomaspp.)。
同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphisgossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Aphis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),Phylloxera vastatrix,Pemphigus spp.,Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodon humuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelisbilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecaniumcorni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphaxstriatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiellaaurantii),Aspidiotus hederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletisblancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutellamaculipennis),菜蛾(Plutella xylostella),天幕毛虫(Malacosomaneustria),Euproctis chrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrix thurberiella),Phyllocnisticitrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Earias insulana),夜蛾属(Heliothisspp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestrabrassicae),Panolis flammea,斜纹夜蛾(Prodenia litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilo spp.),Pyrausta nubilalis,Ephestia kuehniella,大黄螟(Galleriamellonella),袋衣蛾(Tineola bisselliella),网衣蛾(Tineapellionella),褐织叶蛾(Hofmannophila pseudospretella),Cacoecia podana,Capua reticulana,云杉卷叶蛾(Choristoneurafumiferana),葡萄果蠹蛾(Clysia ambiguella),茶黄卷叶蛾(Homonamagnanima),栎绿卷叶蛾(Tortrix viridana),纵卷叶野螟属(Cnaphalocerus spp.)和Aulema oryzae。
鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,Bruchidius obtectus,家天牛(Hylotrupesbajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsadecemlineata),Phaedon cochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachnavarivestis),Atomaria spp.,锯胸谷盗(Oryzaephilussurinamens),象甲属(Anthonomus spp.),米象属(Sitophilusspp.),Otiorrhynchus sulcatus,香蕉蛛基象甲(Cosmopolitessordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hyperaposttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenue spp.),粉蠹(Lyctusspp.),Meligethes aeneus,蛛甲属(Ptinuss pp.),金黄蛛甲(Niptushololeucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Triboliumspp.),黄粉甲(Tenebrio molitor),扣甲属(Agriotes spp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis),Costelytra zealandica和稻水象甲(Lissorhoptus oryzophilus)。
膜翅属(Hymenoptera),例如锯角叶蜂属(Diprions pp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomoriumpharaonis),和胡蜂(Vespa spp.)。
双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophilamelanogaster),家蝇(Muscas pp.),厩蝇(Fannias pp.),红头丽蝇(Calliphora erythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,斑潜蝇属(Liriomyza spp.),螫蝇属(Stomoxysspp.),鼻蝇属(Oestrus spp.),皮蝇属(Hypoderma spp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyiahyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacusoleae),欧洲大蚊(Tipula paludosa),Hylemnia spp.和Liviomyzaspp.。
蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis),和角叶蚤属(Ceratophyllus spp.)。
蛛形纲(Arachnida),例如Scorpio maurus,黑寡妇球腹蛛(Latrodectus mactans)。
蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssusgallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptesspp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),红叶螨属(Tetranychus spp.),半跗线螨属(Hemitarsonemus spp.)和Brevipulus spp.。
植物寄生线虫包括短体线虫属(Pratylenchus spp.),相似穿孔线虫(Radopholus similis),起绒草茎线虫(Ditylenchusdipsaci),半穿刺线虫(Tylenchulus semipenetrans),异皮线虫属(Heterodera spp.),球异皮线虫属(Globodera spp.),根结线虫属(Meloidogyne spp.),滑刃线虫属(Aphelenchoides spp.),长针线虫属(Longidorus spp.),剑线虫属(Xiphinema spp.),毛刺线虫属(Trichodorus spp.)和伞滑刃线虫属(Bursaphelenchus spp.)。
在叶和土壤施用后,本发明活性化合物具有高的杀虫和杀螨活性。
在某些浓度或施用率时,本发明化合物也具有杀真菌作用。此外,它们也可以用作杀菌剂或抗霉菌剂。
当用来防治卫生害虫和贮藏产品的害虫时,活性化合物对木材和陶土具有显著残留作用和对石灰处理过的底物上的碱具有良好的稳定性。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如硬蜱、隐喙蜱科、疥螨、恙螨、(叮咬和吸吮)蝇、寄生蝇幼虫、虱、毛虱、鸟虱和蚤有活性。这些寄生虫包括:
虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、虱属(Pediculus spp.)、阴虱属(Phthirus spp.)、盲虱属(Solenoptes spp.)。
食毛目及amblycerina和细角亚目(Ischnocerina),例如,毛鸟虱属(Trimenopon spp.)、短角鸟虱属(Menopon spp.)、豆虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiellaspp.、Lepikentron spp.、畜虱属(Damalinea spp.)、啮毛虱属(Trichodectes spp.)和猫虱属(Felicola spp.)。
双翅目及长角亚目和短角亚目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simuliumspp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotusspp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、齿股蝇(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、血蝇属(Haematobiaspp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossinaspp.)、丽蝇属(Calliphora spp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hippoboscaspp.)、蜱蝇属(lipoptena spp.)和羊虱蝇属(Melophagus spp.)。
蚤目,例如,蚤属(Pulex spp.)、栉头蚤属(Ctenocephalidesspp.)、鼠客蚤属(Xenopsylla spp.)和毛列蚤属(Ceratophyllusspp.)。
半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatomaspp.)、红腹猎蝽属(Rhodnius spp.)和全圆蝽属(Panstrongylusspp.)。
蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattela germanica)和棕带蠊属(Suppella spp.)。
螨亚纲及后气亚目(Metastigmata)和中气亚目(Mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、残喙蜱属(Otabius spp.)、硬蜱属(Ixodesspp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostoma spp.)和瓦螨属(Varroa spp.)。
Actinedida(前气孔亚目)和粉螨目(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形属(Demodex spp.)、恙螨属(Trombicula spp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophaus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、瘙螨属(Psoroptes spp.)、痒螨属(Chorioptes spp.)、耳癞螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、痂螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、胞螨属(Cytodites spp.)和皮膜螨属(Laminosioptes spp.)。
本发明式(I)活性化合物也适合防治侵害如下动物的节肢动物:牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治这些节肢动物,旨在使死亡和产量(如肉、奶、毛、皮、蛋、蜜等)降低的情况减少。这样,通过使用本发明活性化合物,使更经济简单的动物饲养成为可能。
本发明活性化合物可以使用在兽医方面,使用是以已知的方式,通过外部施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过沐浴或浸蘸、喷雾、浇泼、点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当给药于家畜、家禽、宠物等时,式(I)的活性化合物可以以制剂的形式(例如粉剂、乳剂、悬浮剂)的使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10000倍后施用,或者它们可以以化学浴的形式使用。
然而,现已发现,本发明式(I)化合物对破坏工业材料的昆虫具有强的杀虫作用。
可以列举且是优选的昆虫是下列,但不限于这些昆虫:
甲虫如
北美家天牛(Hylotrupes bajulus)、长毛天牛(Chlorophoruspilosis)、具斑窃蠹(Anobium punctatum)、报死窃蠹(Xestobiumrufovillosum)、梳角细脉窃蠹(Ptilinus pecticornis)、Dendrobium pertinex、松窃蠹(Ernobium mollis)、Priobiumcarpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctusafricanus)、南方粉蠹(Lyctus planicollis)、桴粉蠹(Lyctuslinesris)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、材小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostyrchus capucins)、暗褐长蠹(Heterobostrychusbrunneus)、长蠹属(Sinoxylon spec.)和竹长蠹(Dinoderusminutus)。
革翅目,如
小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigas taignus、U.augur。
白蚁,如
木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermesindicola)、黄胸散白蚁(Reticulitermes flavipes)、Reticulitermes santonecsis、避光散白蚁(Reticulitermeslucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、湿木白蚁(Zootermopsis nevadensis)和家白蚁(Coptotermesformosanus)。
衣鱼
如西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为无生命的材料如优选的是塑料、胶粘剂、粘性材料、纸和板、皮革、木材和木制品、和漆。
木材和木制品是非常特别优选的受保护而使之不被昆虫侵害的材料。
可以用本发明的药剂或含有之的组合物保护的木材和衍生的木制品应理解为有下列含义,例如,建筑木料、木梁、铁道枕木、桥梁组件、船用跳板、木制车辆、板箱、模板、包装箱、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
本发明活性化合物可以以其原样、以其浓缩物或通常的常规制剂使用。所述的常规制剂是例如粉剂、颗粒剂、溶液、悬浮剂、乳剂或膏剂。
上述制剂可以以本身已知的方式制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂、(如果需要)干燥剂和UV稳定剂和(如果需要)着色剂和染料和其它加工辅助剂混合。
用于保护木材和木制品的杀虫组合物或浓缩物包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
所采用的组合物或浓缩物的量取决于昆虫的种类和密度,以及介质。所用最佳量可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足已。
所用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油样有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,且如果适宜是乳化剂和/或润湿剂。
优选采用的有机化学溶剂是油性或油样溶剂,所述的溶剂具有大于35的挥发度和高于30℃的闪点,优选高于45℃。用作这种油性或油样溶剂的物质是低挥发性的,且不溶于水,这类物质适合的有矿物油或其芳族馏份或是含有矿物油的溶剂混合物,优选是石油溶剂、石油和/或烷基苯。
使用沸程为170到220℃的矿物油、沸程为170到220℃的石油溶剂、沸程为250到350℃的碇子油、沸程为160到280℃的石油或松节油精是有利的。
在一个优选的实施方案中,所用的物质是沸程为180至210℃的液体脂族烃或沸程为180至220℃的脂族和芳族烃的高沸点混合物和/或碇子油和/或单氯萘,优选α-单氯萘。
挥发度高于35且闪点高于30℃,优选高于45℃的低挥发性有机油性或油样溶剂,可以部分地由低或中挥发性的有机化学溶剂置换,其前提条件是,溶剂混合物也具有高于35的挥发度且闪点高于30℃,优选高于45℃,且杀虫剂/杀真菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在一个优选的实施方案中,部分有机化学溶剂或溶剂混合物被脂族极性有机化学溶剂或溶剂混合物置换。优选采用的物质是含有羟基和/或酯和/或醚基团的脂族有机化学溶剂,如例如乙二醇醚、酯类等。
在本发明范围内使用的有机化学粘合剂是本身已知的粘合干性油和/或合成树脂,它们可以用水稀释和/或在所采用的有机化学溶剂中是可溶的、可分散的或可乳化的,特别是那些由如下组成,或包含如下成分的粘合剂:丙烯酸树酯、乙烯树脂,例如聚乙酸乙烯酯、聚酯树酯、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、苯酚树脂、烃类树脂如茚-香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
用作粘合剂的合成树脂可以以乳液、分散液或溶液的形式使用。沥青或沥青状物质也可以用作粘合剂的物质,其量至多为按重量计10%。此外,可以采用特别是着色剂、染料、防水剂、遮味剂和抑制剂或抗腐蚀剂。
根据本发明,组合物或浓缩物优选含有至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。根据本发明所优选采用的物质是油含量超过按重量计45%,优选50至68%的醇酸树脂。
所有的或部分上述粘合剂可以由固定剂(混合物)或增塑剂(混合物)置换。这些添加剂是旨在防止活性化合物以及挥发和结晶或沉淀。它们优选置换0.01至30%的粘合剂(以所用的粘合剂的100%为基准)。
增塑剂来自属于下列化学类的物质:邻苯二甲酸酯类,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯类,如磷酸三丁酯,己二酸酯类,如二(2-乙基己基)己二酸酯,硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,如油酸丁酯,甘油醚类或高分子量乙二醇醚类、甘油酯类和对甲苯磺酸酯类。
固定剂化学上基于聚乙烯基烷基醚类如聚乙烯基甲基醚,或酮类如二苯甲酮或亚乙基二苯甲酮。
特别适合的溶剂或稀释剂也可以是水,如果适宜是水与一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别有效的木材保护通过工业规模的浸渍工艺,例如真空、双真空或压力工艺的方式获得。
如果适宜,直接可用的组合物还可以包含其它杀虫剂和如果适宜也可以有一或多种杀真菌剂。
可能混合于其中的另外的适合组分优选是WO 94/29 268中提到的杀虫剂和杀真菌剂。在上述文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、氟硅菊酯、氟氯氰菊酯、甲体氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、啶虫脒、氟虫脲、氟铃脲和杀虫隆,以及杀真菌剂如氟环唑、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、叶菌唑、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明的活性化合物可以特别有效地用于防治损害植物的昆虫,例如抗辣根猿叶甲(Phaedon cochleariae)幼虫、抗黑尾叶蝉(Nephotettixcincticeps)幼虫和抗桃蚜(Myzus persicae)幼虫。
除了所述的杀螨、除草和杀虫性质外,本发明活性化合物的杀真菌活性也是显著的。在“体外”和“体内”研究中,可以观察到广谱杀真菌作用。
此外,注意到活性化合物也特别适用于防治受感染植物的霉、叶斑病和镰孢霉属(Fusaria)。
本发明活性化合物的制备和使用可以参见下列实施例。
制备实施例
实施例1
化合物I-1-a-1
将1.75g 5-乙基-2-甲基-5,6-二氢-2H-1,4-噁嗪-3-基甲基硫化物和1.80g4-氯苯甲酰基乙腈在10ml甲苯中的混合物加热到110℃。通过薄层层析监测反应。一旦原料实际上完全转化后,就将混合物冷却并将其中的化合物在硅胶上用己烷/乙酸乙酯(2∶1)作为流动相进行柱层析分离。
经过蒸发溶剂后,一个主要组分是0.25g(理论量的8.3%)的3-(4-氯苯基)-2-(5-乙基-2-甲基-1,4-噁嗪酮-3-亚基)-3-氧代丙腈,熔点136℃。
1H-NMR(400MHz,d6-DMSO):δ=0.97(t,3H,CH2-CH3);1.62(d,3H,CHCH3);4.76(m,1H,O-CH-CH3);7.56,7.7(2AA′BB′,4H,ArH);12.4(s,1H,NH)ppm.
实施例2
化合物I-1-a-2
将0.6g的3-[3,5-二(三氟甲基)苯基]-2-(2-甲基-1,4-噁嗪烷-3-亚基)-3-氧代丙腈和0.5g的Lawesson氏试剂加热回流2小时。然后将混合物中的反应产物在硅胶上用己烷/乙酸乙酯(2∶1)作为流动相进行柱层析分离。
经过蒸发溶剂后,一个主要组分是0.5g(理论量的85%)的3-[3,5-二(三氟甲基)苯基]-2-(2-甲基-1,4-噁嗪烷-3-亚基)-3-硫代丙腈,熔点195℃。
实施例3
化合物III-1
在0℃,将8.5g的KOH加入到在150ml丙酮中的10.6g的5-乙基-2-甲基-3-吗啉硫酮中。将混合物温热至室温(20℃),加入5ml碘甲烷。将混合物反应4小时,减压下蒸掉溶剂。剩余的固体残留物在硅胶上用己烷/乙酸乙酯(10∶1)进行柱层析分离。
经过蒸发溶剂后,主要组分是7.6g(理论量的65.5%)的5-乙基-2-甲基-5,6-二氢-2H-1,4-噁嗪-3-基甲基硫化物,为黄色油状物。
实施例4
化合物V-1
在室温(20℃)下,将20g的5-乙基-2-甲基-3-吗啉酮和100ml的甲苯的混合物与33g的Lawesson氏试剂混合。然后将反应混合物加热回流24小时。类似于实施例2进行后处理。
得到11.2g(理论量的50%)的5-乙基-2-甲基-3-吗啉硫酮油状物。
实施例5
化合物I-2-A-a-1
将1.0g的6-氯-3-吡啶基乙腈、1.27g的5,6-二氢-2H-1,4-噁嗪-3-基甲基硫化物(类似于实施例3制备)和10ml甲苯的混合物加热到80℃并在该温度下搅拌5小时。然后减压下蒸掉溶剂,给出固体残留物,用甲基叔丁基醚(MTBE)和环己烷的混合物重结晶。干燥所得的熔点为179℃的固体。
给出了1.24g(理论量的85.2%)的3-(6-氯-3-吡啶基)-2-(1,4-噁嗪烷-3-亚基)-3-氧代丙腈。
实施例6
化合物I-1-a-15
(方法G)
将0.5g的3-[3,5-二(三氟甲基)苯基]-2-(1,4-噻嗪烷-3-亚基)-3-氧代丙腈(化合物I-1-a-10)引入到20ml氯仿中,并在20℃下与0.35g的3-氯过苯甲酸混合。通过薄层层析监测反应进程。所有的原料已经转化后,用碳酸氢钠溶液萃取反应产物,在硅胶上用二氯甲烷/乙酸乙酯(10∶1)作为流动相进行柱层析分离。经过蒸发溶剂后,主要组分是0.50g的3-[3,5-二(三氟甲基)苯基]-2-(1,1-二氧代-1λ6,4-噻嗪烷-3-亚基)-3-氧代丙腈,熔点224-226℃。
实施例7
化合物I-1-a-37
(方法E)
在氩气下,将1.2g的3-(3-溴-5-三氟甲基苯基)-2-(2-甲基-1,4-噁嗪酮-3-亚基)-3-氧代丙腈(化合物I-1-a-24)引入到30ml二甲氧基乙烷中并与0.5g的4-氯苯基硼酸、200mg的四(三苯基膦)钯和30ml 2M的碳酸钾溶液混合。将反应混合物在80℃加热过夜。
然后将混合物中的化合物在硅胶上用己烷/乙酸乙酯(2∶1)作为流动相进行柱层析分离。
经过蒸发溶剂后,一个主要组分是0.65g(理论量的52%)的3-[3-(4-氯苯基)-5-三氟甲基苯基]-2-(2-甲基-1,4-噁嗪酮-3-亚基)-3-氧代丙腈,熔点119℃。
类似于实施例1和2并按照式(I-1-a)化合物制备方法的一般描述,得到了下列化合物:
化合物编号 | K | A | m | Y1 | Y2 | Y3 | Y4 | Y5 | Y6 | V | Z | m.p.℃ |
I-1-a-3 | O | 4-Cl | 1 | H | H | C2H5 | H | H | H | O | H | 油状物 |
I-1-a-4 | O | 4-(4-Cl-C6H4),2-F | 1 | H | H | H | H | H | H | O | H | 198 |
I-1-a-5 | O | 4-Cl | 1 | H | H | H | H | H | H | O | H | 192 |
I-1-a-6 | O | 2-CF3 | 1 | H | H | H | H | H | H | O | H | 158 |
I-1-a-7 | O | 3,5-(CF3)2 | 1 | H | H | H | H | H | H | O | H | 164 |
I-1-a-8 | O | 2,4-F2 | 1 | H | H | H | H | H | H | O | H | 179 |
I-1-a-9 | O | 4-CN | 1 | H | H | H | H | H | H | O | H | 224 |
I-1-a-10 | O | 3,5-(CF3)2 | 1 | H | H | H | H | H | H | S | H | 182 |
I-1-a-11 | O | 3,5-(CF3)2 | 1 | H | H | CH3 | CH3 | H | H | O | H | 油状物 |
I-1-a-12 | O | 3,5-(CF3)2 | 1 | H | H | C2H5 | H | H | H | O | H | 油状物 |
化合物编号 | K | A | m | Y1 | Y2 | Y3 | Y4 | Y5 | Y6 | V | Z | m.p.℃ |
I-1-a-13 | O | 3,5-(CF3)2 | 1 | CH3 | H | C2H5 | H | H | H | O | H | 72 |
I-1-a-14 | O | 3,5-(CF3)2 | 1 | CH3 | H | H | H | H | H | O | H | 142 |
I-1-a-15 | O | 3,5-(CF3)2 | 1 | CH3 | H | H | H | H | H | SO2 | H | 224-226 |
I-1-a-16 | O | 4-Cl | 1 | H | H | CH3 | CH3 | H | H | O | H | 102 |
I-1-a-17 | O | 4-Cl | 1 | H | H | H | H | CH3 | H | O | H | 235 |
I-1-a-18 | O | 3,5-(CF3)2 | 1 | H | H | H | H | CH3 | H | O | H | 157 |
I-1-a-19 | O | 3,5-(CF3)2 | 1 | CH3 | H | H | H | CH3 | H | O | H | 142 |
I-1-a-20 | O | 4-Cl | 1 | CH3 | H | H | H | CH3 | H | O | H | 179 |
I-1-a-21 | O | 4-Me | 1 | CH3 | H | H | H | H | H | O | H | 油状物 |
I-1-a-22 | O | 4-Cl | 1 | H | H | H | H | H | H | S | H | 182-184 |
I-1-a-23 | O | 3-(3-Cl-C6H4-O),5-NO2 | 1 | CH3 | H | H | H | H | H | O | H | |
I-1-a-24 | O | 3-Br,5-CF3 | 1 | CH3 | H | H | H | H | H | O | H | 126 |
I-1-a-25 | O | 3,5-(CH3)2 | 1 | CH3 | H | H | H | H | H | O | H | 油状物 |
I-1-a-26 | O | 3,5-Br2 | 1 | CH3 | H | H | H | H | H | O | H | 211 |
I-1-a-27 | O | 3,5-Br2 | 1 | H | H | H | H | H | H | O | H | 226 |
I-1-a-28 | O | 4-Br,2-F | 1 | H | H | H | H | H | H | O | H | 192 |
I-1-a-29 | O | 4-Cl | 1 | CH3 | H | H | H | H | H | O | H | 194 |
I-1-a-30 | S | 4-Cl | 1 | H | H | H | H | H | H | O | H | 194 |
I-1-a-31 | S | 3,5(CF3)2 | 1 | H | H | H | H | H | H | O | H | 217 |
I-1-a-32 | O | 4-Cl | 1 | CH3 | CH3 | H | H | H | H | S | H | 191 |
I-1-a-33 | O | 3,5-(CF3)2 | 1 | CH3 | CH3 | H | H | H | H | S | H | 142 |
I-1-a-34 | O | 4-Cl | 1 | -(CH2)3- | H | H | H | H | S | H | 171 | |
I-1-a-35 | O | 3,5-(CF3)2 | 1 | -(CH2)3- | H | H | H | H | S | H | 156 | |
I-1-a-36 | O | 3-CF3,5-(4-CF3-C6H4) | 1 | CH3 | H | H | H | H | H | O | H | 146 |
I-1-a-37 | O | 3-CF3,5-(4-Cl-C6H4) | 1 | CH3 | H | H | H | H | H | O | H | 119 |
类似于实施例5并按照式(I-1-a)化合物制备方法的一般描述,得到了下列式(I-2-a)化合物:
化合物编号 | K | A | m | Y1 | Y2 | Y3 | Y4 | Y5 | Y6 | V | m.p.℃ |
I-2-A-a-2 | O | 4,6-Cl2 | 1 | H | H | H | H | H | H | O | 140 |
I-2-A-a-2 | O | 2-Cl | 1 | H | H | H | H | H | H | O | 164 |
I-2-A-a-4 | O | 6-Cl | 1 | H | H | CH3 | CH3 | H | H | O | |
I-2-A-a-5 | O | 2-Cl | 1 | CH3 | H | H | H | H | H | O | 140 |
I-2-A-a-6 | O | 4,6-Cl | 1 | CH3 | H | H | H | H | H | O | 108 |
I-2-A-a-7 | O | 6-Cl | 1 | CH3 | H | H | H | H | H | O | 189 |
I-2-B-a-1 | O | 2,6-Cl2 | 1 | CH3 | H | H | H | H | H | O | 174 |
实施例
辣根猿叶甲幼虫试验
溶剂: 31份重量二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将此乳油稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片浸入所需浓度的活性化合物制剂,在叶片仍湿润时,移接辣根猿叶甲(Phaedon cochleariae)幼虫。
在所需的一段时间后,测定死亡百分率。100%指甲虫幼虫均被杀死;0%指没有甲虫幼虫被杀死。
在此试验中,例如,制备实施例I-1-a-10化合物显示出好的活性。
实施例
斜纹夜蛾试验
溶剂: 31份重量二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂和所述量的乳化剂混合,并用含乳化剂的水将此乳油稀释至所需浓度。
将所述量的所需浓度的活性化合物制剂吸移到标准化量的合成食物中。重复6次后,在每种情况下将一只斜纹夜蛾(Spodopterafrugiperda)幼虫(L3)置于食物上。
在所需的一段时间后,测定死亡百分率。100%指动物均被杀死;0%指没有动物被杀死。
在此试验中,例如,制备实施例I-1-a-14化合物显示出好的活性。
实施例
烟芽夜蛾试验
溶剂: 30份重量二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将此乳油稀释至所需浓度。
将大豆新芽(Glycine max)浸入所需浓度的活性化合物制剂,在叶片仍湿润时,移接烟芽夜蛾(Heliothis virescens)毛虫。
在所需的一段时间后,测定死亡百分率。100%指毛虫均被杀死;0%指没有毛虫被杀死。
在此试验中,例如,制备实施例I-1-a-14化合物显示出好的活性。
实施例
叶螨试验(抗OP/浸蘸处理)
溶剂: 30份重量二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并用含乳化剂的水将此乳油稀释至所需浓度。
将长满所有发育虫期二点叶螨(Tetranychus urticae)的菜豆(Phaseolus vulgaris)植株浸入所需浓度的活性化合物制剂。
在所需的一段时间后,测定死亡百分率。100%指叶螨均被杀死;0%指没有叶螨被杀死。
在此试验中,例如,制备实施例I-1-a-10和I-1-a-7化合物显示出好的活性。
实施例
芽后试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。
三周后,将植物的损害程度与未处理对照相比较,计算损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,制备实施例I-1-a-7、I-1-a-8和I-1-a-9的化合物对杂草显示出非常强的活性,它们中的一些能被作物如小麦很好地耐受。
实施例
芽前试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中,24小时后,土壤用活性化合物制剂浇水,有利的是保持单位面积上的水量恒定。活性化合物在制剂中的浓度并不重要。只有单位面积上活性化合物的施用率是重要的。三周后,将植物的损害程度与未处理对照的发育相比较,计算损害%。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全损害
在此试验中,制备实施例I-1-a-3、I-1-a-7、I-1-a-8和I-1-a-9的化合物对杂草显示出非常强的活性,它们中的一些能被作物如小麦和大豆很好地耐受。
Claims (6)
1.通式(I)的化合物,
其中
K代表氧或硫,
Ar代表Ar1,该Ar1代表被卤素、C1-C8-烷基、C1-C8-卤代烷基、氰基或硝基单-至五取代的苯基;或者代表Ar2,该Ar2代表Ar1,该Ar1还被苯基或苯氧基取代,其中所述的苯基或苯氧基取代基本身被卤素或C1-C4-卤代烷基单-至四取代;或代表被卤素单-至五取代的吡啶基,
V代表-O-、-S-或-SO2-,
X代表CN,
Y1和Y3代表氢或C1-C6-烷基,
Y2、Y4、Y5和Y6代表氢或C1-C4-烷基,
或
Y1和Y2与它们所连的碳原子一起代表C3-C6-环烷基环,
Z代表氢,和
m代表1。
2.根据权利要求1的化合物,其特征在于:
K代表氧或硫,
Ar代表Ar1,该Ar1代表被氟、氯、溴、甲基、乙基、丙基、异丙基、正-、异-、仲-或叔丁基、三氟甲基、氰基或硝基单-至三取代的苯基;或代表Ar2,该Ar2代表Ar1,该Ar1还被苯基或苯氧基取代,其中所述的苯基或苯氧基取代基本身被氟、氯、溴或三氟甲基单-或二取代;或者代表被氟、氯或溴单-至三取代的吡啶基,
V代表-O-或-S-,
X代表CN,
Y1和Y3代表氢、甲基、乙基或丙基,
Y2、Y4、Y5、Y6代表氢、甲基或乙基,
Z代表氢,和
m代表1。
3.制备权利要求1的化合物的方法,其特征在于:
(A)如果K代表氧和Z代表氢,则任选地在稀释剂存在下,任选地在碱或酸和/或式(IIIa)的金属化合物存在下,
Me(Q)2 (IIIa)
其中,
Me代表二价过渡金属原子,和
Q代表螯合物配体,
使式(II)化合物与式(III)化合物反应,
其中
Ar和X如权利要求1中所定义,
其中
V、Y1、Y2、Y3、Y4、Y5、Y6和m如权利要求1中所定义,和
A代表O或S(O)q,其中q代表0或2,
R11代表C1-C6烷基或苄基,或
(B)如果K代表氧和Z代表氢,则任选地在稀释剂存在下,使式(IV)化合物与式(V)化合物反应,得到了式(VI)化合物,
其中
Ar和X如权利要求1中所定义,和
Hal代表卤素,
其中
V、Y1、Y2、Y3、Y4、Y5、Y6和m如权利要求1中所定义,
其中
V、Ar、X、Y1、Y2、Y3、Y4、Y5、Y6和m如权利要求1中所定义,任选地在碱存在下和任选地在三价磷化合物存在下使式(VI)化合物进一步反应消除硫和卤化氢,得到其中K代表氧和Z代表氢的权利要求1的化合物,或
(E)如果K代表氧,则在溶剂存在下,任选地在碱和贵金属配合物存在下,使式(I1)化合物与式(X)的硼酸反应,
其中
Ar1、V、X、Y1、Y2、Y3、Y4、Y5、Y6、Z和m如权利要求1中所定义,和
Hal代表卤素,
Ar2’-B(OH)2 (X)
其中
Ar2’代表苯基或苯氧基,该苯基或苯氧基本身被卤素或C1-C4-卤代烷基单-至四取代,或
(F)如果K代表硫,则在溶剂存在下,在硫化剂存在下,使下列式(I)化合物反应,
其中
Ar、Z、V、X、Y1、Y2、Y3、Y4、Y5、Y6和m如权利要求1中所定义,
和
K代表氧,或
(G)如果V代表S(O)n和n代表2,则在过酸或过氧化氢存在下在钼酸盐或钨酸盐存在下氧化下式(I)化合物,
其中
Ar、Z、K、X、Y1、Y2、Y3、Y4、Y5、Y6和m如权利要求1中所定义,和
V代表硫原子。
4.防治不希望的植物和/或动物害虫的方法,其特征在于,使至少一种权利要求1-2任一项中定义的化合物作用于不希望的植物和/或动物害虫和/或其环境。
5.至少一种权利要求1-2任一项中定义的化合物防治不希望的植物和/或动物害虫的用途。
6.除草、杀螨或杀虫组合物,其特征在于它包含权利要求1-2任一项中定义的化合物和常规的扩充剂和/或表面活性剂。
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JP2004137270A (ja) * | 2002-09-26 | 2004-05-13 | Nippon Nohyaku Co Ltd | 新規除草剤、その使用方法、新規置換チエノピリミジン誘導体及びその中間体並びにそれらの製造方法 |
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US7812163B2 (en) | 2003-07-16 | 2010-10-12 | Hatchtech Pty Ltd. | Methods and compositions for controlling ectoparasites |
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EA031732B1 (ru) | 2013-12-17 | 2019-02-28 | Др. Редди'С Лабораторис, С.А. | Педикулицидная композиция |
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FR2688781B1 (fr) | 1992-03-23 | 1994-07-01 | Sanofi Elf | Imidazolines n-substituees par un groupement biphenylmethyle, leur preparation, les compositions pharmaceutiques en contenant. |
US5891897A (en) | 1995-04-27 | 1999-04-06 | Nissan Chemical Industries, Ltd. | Oxopropionitrile derivative and vermin controlling agent |
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- 2000-11-21 KR KR1020027005878A patent/KR100762442B1/ko not_active IP Right Cessation
- 2000-11-21 WO PCT/EP2000/011838 patent/WO2001040202A1/de active IP Right Grant
- 2000-11-21 EP EP00977587A patent/EP1259496A1/de not_active Withdrawn
- 2000-11-21 US US10/130,891 patent/US7186829B1/en not_active Expired - Fee Related
- 2000-11-21 JP JP2001541887A patent/JP2003515596A/ja not_active Withdrawn
- 2000-11-21 PL PL00355678A patent/PL355678A1/xx not_active Application Discontinuation
- 2000-11-21 CN CN008166757A patent/CN1216874C/zh not_active Expired - Fee Related
- 2000-11-21 CA CA002394002A patent/CA2394002A1/en not_active Abandoned
- 2000-11-30 AR ARP000106318A patent/AR035020A1/es not_active Application Discontinuation
- 2000-12-01 TW TW089125532A patent/TW542828B/zh active
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Also Published As
Publication number | Publication date |
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CN1407977A (zh) | 2003-04-02 |
TW542828B (en) | 2003-07-21 |
MXPA02005398A (es) | 2003-02-12 |
CO5231185A1 (es) | 2002-12-27 |
KR100762442B1 (ko) | 2007-10-04 |
PL355678A1 (en) | 2004-05-04 |
CA2394002A1 (en) | 2001-06-07 |
US20060069253A1 (en) | 2006-03-30 |
AU775400B2 (en) | 2004-07-29 |
BR0016151A (pt) | 2002-08-13 |
KR20020059699A (ko) | 2002-07-13 |
AR035020A1 (es) | 2004-04-14 |
WO2001040202A1 (de) | 2001-06-07 |
JP2003515596A (ja) | 2003-05-07 |
DE19958164A1 (de) | 2001-06-07 |
US7186829B1 (en) | 2007-03-06 |
AU1524501A (en) | 2001-06-12 |
EP1259496A1 (de) | 2002-11-27 |
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