TWI391094B - N-經對掌性二環基團取代之胺基-1,3,5-三嗪化合物,其製法,組成物及其用作除草劑和植物生長調節劑之用途 - Google Patents
N-經對掌性二環基團取代之胺基-1,3,5-三嗪化合物,其製法,組成物及其用作除草劑和植物生長調節劑之用途 Download PDFInfo
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- TWI391094B TWI391094B TW100101093A TW100101093A TWI391094B TW I391094 B TWI391094 B TW I391094B TW 100101093 A TW100101093 A TW 100101093A TW 100101093 A TW100101093 A TW 100101093A TW I391094 B TWI391094 B TW I391094B
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- 239000000203 mixture Substances 0.000 title description 86
- 239000004009 herbicide Substances 0.000 title description 44
- 238000000034 method Methods 0.000 title description 43
- 238000002360 preparation method Methods 0.000 title description 22
- 239000005648 plant growth regulator Substances 0.000 title description 4
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 title description 2
- 230000008569 process Effects 0.000 title description 2
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- 150000003839 salts Chemical class 0.000 claims description 43
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- 229910052731 fluorine Inorganic materials 0.000 claims description 31
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 30
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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- 125000004432 carbon atom Chemical group C* 0.000 description 20
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 235000009566 rice Nutrition 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 6
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- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000012360 testing method Methods 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- 229960002312 tolazoline Drugs 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
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical compound COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 229950001577 trimetozine Drugs 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 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
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Description
本發明係關於某些2-胺基-4-(二環基)胺基-6-(經取代之烷基)-1,3,5-三嗪衍生物之具旋光性的異構物、彼等之製法、彼等之組成物及中間物、以及彼等用作為供控制非所要之植物或草木的除草劑或植物生長調節劑的用途。
WO 97/31904及EP-A-0864567記載了2-胺基-4-二環基-胺基-1,3,5-三嗪類的製備以及彼等化合物作為除草劑及植物生長調節劑的用途。該參考資料一般性地記載了各種經某些基團所取代的胺基-1,3,5-三嗪衍生物,彼等大體上包含了一或多個對掌中心。然而,經特定揭示的衍生物係僅記載為立體異構物的混合物,諸如,鏡像異構物的消旋混合物或是呈消旋形式之非鏡像異構物的混合物。在某些情況下,已知的化合物在使用時,會有,例如,對抗有害植物的除草作用不足,與天氣、氣候及/或土壤條件有關之施用限制過於嚴格、對抗雜草的作用譜過於狹窄或是作物的選擇性過小等缺點。
出乎意料地,吾人發現到某些經取代之2-胺基-1,3,5-三嗪衍生物的特定具旋光性之異構物與先前技藝的化合物或是其對應的消旋化合物或其他光學異構物相較之下,具有有利的施用性質。例如,彼等為非常具有活性的除草劑,可用於控制廣泛的有害雜草,出乎意料地,與彼等之立體異構物或消旋混合物相較之下,具有更佳強效的除草功效。
本發明係關於式(I)所示之具旋光性的化合物或其農業上可接受之鹽類
式中:R1
為H、鹵素、(C1
-C6
)烷基、(C1
-C6
)鹵烷基、[(C1
-C4
)烷氧基](C1
-C6
)烷基、(C3
-C6
)環烷基(其係未經取代或是經一或多個選自鹵素、(C1
-C4
)烷基及(C1
-C4
)鹵烷基的基團所取代)、或為(C2
-C6
)烯基、(C2
-C6
)炔基、(C2
-C6
)鹵烯基、(C4
-C6
)環烯基、(C4
-C6
)鹵環烯基、(C1
-C6
)烷氧基或是(C1
-C6
)鹵烷氧基;R2
為H、鹵素、(C1
-C6
)烷基或(C1
-C4
)烷氧基;或是R1
及R2
可與所連接的碳原子一起形成(C3
-C6
)環烷基或(C4
-C6
)環烯基環;R3
為H、(C1
-C6
)烷基、(C1
-C4
)烷氧基或鹵素;R4
及R5
各自獨立為H、(C1
-C4
)烷基、(C1
-C4
)鹵烷基、(C3
-C4
)烯基、(C3
-C4
)鹵烯基、(C3
-C4
)炔基、(C3
-C4
)鹵炔基或是醯基基團;R6
為H、(C1
-C6
)烷基或(C1
-C6
)烷氧基;R7
、R8
、R9
及R10
各自獨立為H、(C1
-C4
)烷基、(C1
-C3
)鹵烷基、鹵素、(C1
-C3
)烷氧基、(C1
-C3
)鹵烷氧基或CN;A為CH2
、O或是直接鍵;且在標記為1之位置上的立體化學構型(R),其立體化學純度為60至100%(R)(宜為70-100%(R),尤指80-100%(R)),基於在該位置上之具有(R)-及(S)-構型的立體異構物含量。
供參照所用,在式(I)中,某些環碳原子係標記為1至3,而鍵結至三嗪環的碳原子係標記為1*。
在本發明中,在標記為1之位置上的立體化學構型,根據Cahn-Ingold-Prelog系統,係優勢地固定為(R),但是,本發明的標的亦關於式(I)所涵蓋之在其他位置的所有立體異構物及彼等之混合物。如是之式(I)化合物含有,例如,一或多個未特定標示於式(I)之其他不對稱中心或雙鍵。本發明理當亦既包括純異構物又包括多少富含彼等純異構物的混合物,其中在標記為1之位置上的不對稱碳原子係呈R-構型或是,在混合物的情況下,具有相同化學組成的化合物或多個化合物在標記為1之位置係呈R-構型或是彼等化合物的存在比例使得具有R-構型的化合物佔優勢(至少60% R-構型),然而其他不對稱碳原子則可呈消旋形式或是亦可大致已解析。倘若在標記為1之位置上的立體化學構型條件已符合,則以彼等之特定空間形式所定義的可能立體異構物,諸如,鏡像異構物、非鏡像異構物、Z-及E-異構物,皆涵蓋在式(I)的範圍內且可藉由慣用的方法,由立體異構物的混合物得到,或是可藉由採用立體選擇性反應連同立體化學上純的起始物之使用,而得到。
視基團R1
、R2
及R3
的定義而定,前文所指出之一可能的額外不對稱中心為式(I)中標記為1*的碳原子,在該情況下,依據本發明之式(I)化合物可以至少二種純立體異構型的形式存在,亦即,選自原則上存在之四種純立體異構型的(1R,1*R)及(1R,1*S)。另一個不對稱中心亦可出現在式(I)中標記為2的碳原子上,在該情況下,本發明之化合物可以至少四種純立體異構型的形式存在,此等額外的不對稱碳原子各可具有根據Cahn-Ingold-Prelog系統的(R)或(S)構型,亦即,具有構型(1R,1*R,2R)、(1R,1*R,2S)、(1R,1*S,2R)以及(1R,1*S,2S)的純異構物,彼等構型係選自原則上存在的八種純立體異構物。此外,視基團R1
、R2
、R3
、R4
、R5
、R6
、R7
、R8
、R9
及R10
的性質而定,還可有其他的不對稱碳存在。在下文所示的通式中,特定的立體化學構型係界定在任何可能的位置上(除非另有說明),例如,標記為1、2或1*的碳原子,意指在標記位置上的立體化學純度為60至100%,以70-100%較佳,尤指80-100%,最佳為100%。「立體化學純度」係指所述之立體異構物的量,以相對於具有所指定之對掌中心之立體異構物總量的百分比表示。
本發明亦涵蓋任何的酮基及烯醇互變異構物形式以及彼等之混合物及鹽類,若個別的官能基存在的話。
式(I)化合物可藉由添加適當之無機或有機酸至鹼性基(諸如,例如,胺基或烷胺基),而形成鹽類,該無機或有機酸為,諸如,例如,HCl、HBr、H2
SO4
或HNO3
,或是單-或二官能羧酸或磺酸。
某些式(I)化合物可藉由添加適當之無機或有機鹼,而形成鹽類。如是之式(I)化合物具有含有「酸性氫原子」的官能基(諸如,羧基或磺醯基),彼等官能基可為醯基定義中的取代基。此等鹽類的例子為金屬鹽類(尤指,鹼金屬鹽類或鹼土金屬鹽類,宜為鈉或鉀鹽)、或是未經取代或經取代的銨鹽類(諸如,銨鹽類或有機胺類的鹽類、或是四級銨鹽類)。
在本說明書中(包括申請專利範圍的部分),前文所提及的取代基具有下列定義:鹵素係指氟、氯、溴或碘。
在基團名稱之前接有「鹵基」係指該基團部分或完全被鹵化,換言之,被F、Cl、Br、或I以任何的組合取代。
「(C1
-C6
)烷基」一詞係指具有1、2、3、4、5或6個碳原子(在括號中以C-原子數範圍表示)之未分枝或有分枝的非環狀飽和烴類子團,諸如,例如,甲基、乙基、丙基、異丙基、1-丁基、2-丁基、2-甲基丙基或第三丁基基團。此一說明亦適用於在組合基團(諸如,烷氧基烷基)中的烷基。
烷基基團以及在組合基中者(除非另有說明)宜具有1至4個碳原子。
「(C1
-C6
)鹵烷基」係指在「(C1
-C6
)烷基」之說明部分所指出的烷基,但其中有一或多個氫原子被數目相同之相同或不同的鹵素原子所取代,諸如,單鹵烷基(例如,CH2
F、CH2
Cl、CH2
Br、CH2
Cl、CH2
CH2
F、CH2
CH2
Cl、CH2
CH2
Br、CH2
CH2
I、CHFCH3
)、或是過鹵烷基,諸如,CF3
、CCl3
、CF2
CF3
、CCl2
CCl3
、CF2
CCl3
及CCl2
CClF2
)、或是CHF2
、CF3
CH2
、CHF2
CF2
、CH2
FCHCl或CHCl2
。較佳為「(C1
-C4
)鹵烷基」,尤指單鹵烷基、過鹵烷基、CF3
、CHF2
、CH2
F、CHFCH3
、CF2
CF3
、CH2
FCHCl、CH2
Cl、CCl3
、CHCl2
或CH2
CH2
Cl。
「[(C1
-C4
)烷氧基](C1
-C6
)烷基」係指被(C1
-C4
)烷氧基所取代的(C1
-C6
)烷基。
「(C1
-C6
)烷氧基」係指碳鏈的定義如「(C1
-C6
)烷基」部分所定義之烷氧基。「鹵烷氧基」為,例如,OCF3
、OCHF2
、OCH2
F、CF3
CF2
O、OCH2
CF3
或OCH2
CH2
Cl。
「(C2
-C6
)烯基」係指具有所述範圍內之碳原子數之無分枝或有分枝的非環狀碳鏈且其含有至少一個位於個別不飽和基團之任何位置上的雙鍵。「(C2
-C6
)烯基」因此係指,例如,乙烯基、烯丙基、2-甲基-2-丙烯基、2-丁烯基、戊烯基、2-甲基戊烯基或己烯基。
「(C2
-C6
)炔基」係指具有所述範圍內之碳原子數之無分枝或有分枝的非環狀碳鏈且其含有至少一個位於個別不飽和基團之任何位置上的叁鍵。因此,「(C2
-C6
)炔基」係指,例如,炔丙基、1-甲基-2-丙炔基、2-丁炔基或3-丁炔基。
「(C3
-C6
)環烷基」係指單環的烷基基團,諸如,環丙基、環丁基、環戊基或環己基基團。
「(C4
-C6
)環烯基」係指具有4至6個碳原子之碳環、非芳族、部分不飽和的環,例如,1-環丁烯基、2-環丁烯基、1-環戊烯基、2-環戊烯基、3-環戊烯基、或1-環己烯基、2-環己烯基、3-環己烯基、1,3-環己二烯基或是1,4-環己二烯基。
廣義而言,醯基係指自有機酸去除OH基所形成的有機酸基團,例如,羧酸的基團以及由酸類所衍生得的基團(諸如,硫代羧酸、未經取代或N-經取代的亞胺基羧酸)或是碳酸單酯類、未經取代或N-經取代之胺甲酸、未經取代或N-經取代之硫代胺甲酸、磺酸類、亞磺酸類、膦酸類以及一元膦酸類的基團。醯基為,例如,甲醯基、烷羰基(諸如,[(C1
-C4
)烷基]羰基)、苯羰基、烷氧羰基、苯氧羰基、苄氧羰基、烷磺醯基、烷亞磺醯基、苯磺醯基、N-烷基-1-亞胺基烷基以及其他有機酸類的基團。在本文中,彼等基團可在各烷基或苯基的部分更進一步被取代,例如,在烷基部分,被一或多個選自鹵素、烷氧基、苯基及苯氧基的基團所取代;在苯基部分的取代基例子為單-或多取代之(宜多至三取代)相同或互異之選自下列的基團:鹵素、(C1
-C4
)烷基、(C1
-C4
)烷氧基、(C1
-C4
)鹵烷基、(C1
-C4
)鹵烷氧基及硝基,例如,鄰-、間-及對甲苯基,二甲基苯基,2-、3-及4-氯苯基,2-、3-及3-三氟-及-三氯苯基,2,4-、3,5-、2,5-及2,3-二氯苯基,鄰-、間-及對-甲氧基苯基。該醯基基團通常具有1至24個碳原子,宜為1至18,更佳為1至12,最佳為1至7,尤其為1至4。
狹義而言,醯基為,例如,烷酸的基團、烯酸的基團、炔酸的基團或芳基羧酸的基團(例如,苄醯基),或為,例如,烷氧羰基、烯氧羰基、炔氧羰基、芳氧羰基、烷磺醯基、烷亞磺醯基或苯磺醯基;更狹義而言,醯基為烷酸的基團,例如,(C1
-C24
)烷酸的基團,宜為(C1
-C18
)烷酸的基團,尤指(C1
-C12
)烷酸的基團,更特別的為(C1
-C6
)烷酸,諸如,甲醯基、乙醯基或丙醯基。
在定義中所出現之「一或多個選自下列的基團」的表現應被瞭解為在各情況下,選自所指定基團族群之一或多個相同或互異的基團係已被明確界定,除非另有特定的限制。
藉由變數的組合,該通式可能形式上地界定了不安定的官能基,例如,胺甲醯基團或羥基羰氧基,彼等在中性或酸性含水介質中不安定且因此,非為較佳者或是分別以彼等之安定鹽類或降解產物,來使用。
本發明之式(I)化合物或彼等之鹽類中,個別基團具有前述或下文所述之較佳定義者(尤其是表實施例中所列出者),或是(尤其是)其中有二或多個前述或下文所述較佳定義的組合者,乃特別重要的,這主要是因為彼等化合物具有較強效的除草作用、較佳的選擇性及/或更加容易製備。
特別重要的的式(I)化合物乃其中選自R1
、R2
、R3
、R4
、R5
、R6
、R7
、R8
、R9
、R10
及A基團中之一基團宜如下文所定義者,其中該基團的定義係取決於該族群中其中基團的定義。較佳的式(I)化合物含有包含二或多個下文所述較佳定義之該族群內之基團的組合。
較佳地,R1
為H、鹵素、(C1
-C4
)烷基、(C1
-C4
)鹵烷基、[(C1
-C4
)烷氧基](C1
-C4
)烷基、(C3
-C6
)環烷基(其為未經取代或是經一或多個(宜為一或二個)(C1
-C4
)烷基所取代)、(C3
-C4
)鹵環烷基、(C2
-C4
)烯基、(C2
-C4
)炔基、(C2
-C4
)鹵烯基、(C1
-C4
)烷氧基或是(C1
-C4
)鹵烷氧基;更佳地,R1
為H、鹵素、(C1
-C4
)烷基、(C3
-C6
)環烷基或(C1
-C4
)烷氧基;再更佳地,R1
為H或(C1
-C4
)烷基;最佳的是,R1
為H或(C1
-C3
)烷基,尤指H、甲基或乙基。
較佳地,R2
為H或(C1
-C4
)烷基;更佳的是,R2
為H。
R1
及R2
宜與所連結的碳一同形成(C3
-C6
)環烷基環,尤指(C3
-C4
)環烷基。
較佳地,R3
為H、(C1
-C4
)烷基、(C1
-C4
)烷氧基或鹵素,更佳的是,R3
為H、(C1
-C3
)烷基、(C1
-C4
)烷氧基、Cl或F;再更佳地,R3
為H、(C1
-C2
)烷基、甲氧基、氯基或氟基。
R4
宜為H、(C1
-C4
)烷基、(C1
-C4
)鹵烷基、(C3
-C4
)烯基、(C3
-C4
)炔基或是具有1至12個碳原子之醯基,該醯基宜選自CHO、-CO(C1
-C6
)烷基、-CO(C1
-C6
)鹵烷基、-CO2
(C1
-C6
)烷基、-SO2
(C1
-C6
)烷基、-CO2
-苯基或-CO-苯基,其中各苯基係未經取代或是經一或多個選自下列的基團所取代:鹵素、(C1
-C2
)烷基、(C1
-C2
)鹵烷基、(C1
-C2
)烷氧基、(C1
-C2
)鹵烷氧基及NO2
;更佳的是,R4
為H、(C1
-C3
)烷基、(C1
-C3
)鹵烷基、烯丙基、炔丙基、CHO、-CO(C1
-C3
)烷基或-CO(C1
-C3
)鹵烷基;再更佳地,R4
為H、CHO、COCH3
、COCH2
Cl、COCH(CH3
)Cl或COCF3
;最佳的是,R4
為H。
較佳地,R5
為H、(C1
-C4
)烷基或(C1
-C4
)鹵烷基,更佳地,R5
為H或(C1
-C2
)烷基;最佳的是,R5
為H。
R6
宜為H、(C1
-C3
)烷基或(C1
-C3
)烷氧基;更佳的是,R6
為H、甲基或乙基。
較佳地,R7
、R8
、R9
及R10
各自獨立為H、(C1
-C3
)烷基、鹵素或(C1
-C3
)烷氧基;更佳的是,R7
、R8
、R9
及R10
各自獨立為H、甲基、F或Cl。
A宜為CH2
或直接鍵。
較佳的式(I)化合物乃具有下列定義者:R1
為H、鹵素、(C1
-C4
)烷基(諸如,甲基、乙基、正丙基或異丙基)、(C1
-C4
)鹵烷基、[(C1
-C4
)烷氧基](C1
-C4
)烷基、(C3
-C6
)環烷基(其係未經取代或是經一或二個(C1
-C4
)烷基所取代)、(C3
-C4
)鹵環烷基、(C2
-C4
)烯基、(C2
-C4
)鹵烯基、(C2
-C4
)炔基、(C1
-C4
)烷氧基或(C1
-C4
)鹵烷氧基;R2
為H或(C1
-C4
)烷基;或是R1
及R2
與所連接的碳一起形成(C3
-C6
)環烷基環;R3
為H、(C1
-C4
)烷基、(C1
-C2
)烷氧基或鹵素(更宜為H、(C1
-C3
)烷基、甲氧基、Cl或F);R4
為H、(C1
-C4
)烷基、(C1
-C4
)鹵烷基、(C3
-C4
)烯基、(C3
-C4
)炔基或具有1至12個碳原子之醯基基團(宜為CHO、-CO(C1
-C6
)烷基、-CO(C1
-C6
)鹵烷基、-CO2
(C1
-C6
)烷基、-SO2
(C1
-C6
)烷基、-CO2
-苯基或-CO-苯基,其中各苯基係未經取代或是經一或多個選自下列的基團所取代:鹵素、(C1
-C2
)鹵烷基、(C1
-C2
)烷氧基、(C1
-C2
)鹵烷氧基以及NO2
);R5
為H、(C1
-C4
)烷基或(C1
-C4
)鹵烷基;R6
為H、(C1
-C3
)烷基或(C1
-C3
)烷氧基;R7
、R8
、R9
及R10
各自獨立為H、(C1
-C3
)烷基、鹵素或(C1
-C3
)烷氧基;且A為CH2
、O或直接鍵(較佳的是,A為CH2
或直接鍵,尤指直接鍵)。
更佳之式(I)化合物為具有下列定義者:R1
為H或(C1
-C3
)烷基;R2
為H或(C1
-C3
)烷基;或是R1
及R2
與所連結的碳原子一起形成(C3
-C4
)環烷基環;R3
為H、(C1
-C2
)烷基、甲氧基、C1或F;R4
為H、(C1
-C3
)烷基、(C1
-C3
)鹵烷基、烯丙基、炔丙基、CHO、-CO(C1
-C3
)烷基或-CO(C1
-C3
)鹵烷基;R5
為H或(C1
-C2
)烷基;R6
為H、(C1
-C3
)烷基或(C1
-C3
)烷氧基;R7
、R8
、R9
及R10
各自獨立為H、甲基、F及Cl;且A為CH2
、O或直接鍵(較佳的是,A為CH2
或直接鍵,尤指直接鍵)。
特別較佳的式(I)化合物係具有下列定義者:R1
為H或(C1
-C2
)烷基;R2
為H或(C1
-C2
)烷基;或是R1
及R2
與所連結的碳原子-起形成環丙基環;R3
為H、(C1
-C2
)烷基、C1或F;R4
為H;R5
為H;R6
為H或(C1
-C3
)烷基;R7
、R8
、R9
及R10
各自獨立為H、甲基、F及Cl;且A為CH2
、O或直接鍵。
在式(I)內,式CR1
R2
R3
所示之基團宜為選自下列的基團:(C1-C4
)烷基、(C1
-C4
)鹵烷基、(C3
-C4
)環烷基、1-(C1
-C3
)烷基-(C3
-C4
)環烷基及(C3
-C4
)鹵烷基;更宜為(C1
-C3
)烷基、(C1
-C4
)氟烷基、(C1
-C4
)氯烷基、(C3
-C4
)環烷基、1-(C1
-C3
)烷基-(C3
-C4
)-環烷基、(C3
-C4
)-氟環烷基或(C3-C4
)氯環烷基;例如,諸如下列的基團:甲基、乙基、正丙基、異丙基、正丁基、2-丁基、異丁基、第三丁基、1-氟基-乙基、1-氟基-丙基、1-氟基-異丙基、1-氟基-正丁基、1-氯基-乙基、1-氯基-丙基、1-氯基-異丙基、1-氯基-正丁基、1-甲基-環丙基、1-氯基-環丙基或1-氟基-環丙基。
本發明之一較佳體系係關於式(Ia)所示之具旋光性的化合物或其鹽類,其中,標記為1及1*的碳原子以及標記為2的碳原子係非對掌性的:
式中:R1
、R2
及R3
係如式(I)中所定義者,但是先決條件為:R1
、R2
及R3
係構造上互異的;其他之各種代號係如式(I)中所定義者,且標記為1之碳原子上的立體化學構型係如式(I)中所定義者,而在標記為1*之碳原子上的立體化學為(R)或(S)構型或是彼等之混合物,亦包括消旋混合物(R,S),較佳的是,該消旋構型或過量之(R)或(S)構型係佔(R)及(S)構型之總量的60至100%,尤其為70至100%,最佳為80至100%。
更佳者為具有下列定義的式(Ia)化合物:R1
為H、(C1
-C6
)烷基或(C1
-C6
)烷氧基;R2
為H或(C1
-C4
)烷基;R3
為H、(C1
-C4
)烷基或鹵素;R4
及R5
各為H;R6
為H;R7
、R8
、R9
及R10
各自獨立為H、(C1
-C6
)烷基或鹵素;且A為CH2
、O或直接鍵(更佳的是,A為CH2
或直接鍵,尤指直接鍵);先決條件為:R1
、R2
及R3
係構造上互異的。
又較佳者為具有下列定義的式(Ia)化合物:R1
為H、甲基或乙基;R2
為H;R3
為H、F、Cl、甲基或乙基;R4
及R5
各為H;R6
為H;R7
、R8
及R9
各自獨立選自H、甲基、Br、Cl或F;且A為CH2
、O或直接鍵(更佳的是,A為CH2
或直接鍵,尤指直接鍵);先決條件為:R1
、R2
及R3
係構造上互異的。
本發明之第二個較佳體系係關於式(Ib)所示之具旋光性的化合物或其鹽類,其中,標記為1及2的碳原子及標記為1*的碳原子係非對掌性的:
式中:R1
、R2
及R3
係如式(I)中所定義者,先決條件為:R1
、R2
及R3
中至少有二者係構造上相同的;R6
為(C1
-C6
)烷基;其他各種代號係如式(I)中所定義者;且在標記為1之碳原子上的立體化學構型係如式(I)中所定義者;而在標記為2之碳原子上的立體化學係(R)或(S)構型或是彼等之混合物,亦包括消旋構型(R,S),較佳的是,該消旋構型或過量之(R)或(S)構型係佔(R)及(S)構型之總量的60至100%,尤其為70至100%,最佳為80至100%。
亦為較佳者為具有下列定義的式(Ib)化合物:R1
為H、(C1
-C6
)烷基或(C1
-C6
)烷氧基;R2
為H或(C1
-C4
)烷基;或是R1
及R2
可與所連結的碳原子一起形成(C3
-C6
)環烷基環;R3
為H、(C1
-C4
)烷基或鹵素;R4
及R5
各為H;R6
為(C1
-C6
)烷基;R7
、R8
及R9
各自獨立為H、(C1
-C6
)烷基或鹵素;且A為CH2
、O或直接鍵(更佳的是,A為CH2
或直接鍵,尤指直接鍵);先決條件為:R1
、R2
及R3
中至少有二者係構造上相同的。
還更佳者為具有下列定義的式(Ib)化合物:R1
為H、甲基或乙基;R2
為H;R3
為H、F、Cl、甲基或乙基;R4
及R5
各為H;R6
為(C1
-C4
)烷基;R7
、R8
、R9
及R10
各自獨立選自H、甲基、Br、Cl或F;且A為CH2
、O或直接鍵(更佳的是,A為CH2
或直接鍵,尤指直接鍵);先決條件為:R1
、R2
及R3
中至少有二者係構造上相同的。
本發明之第三個較佳體系係關於式(Ic)所示之具旋光性的化合物或其鹽類,其中標記為1、2及1*的碳原子皆為對掌性的:
式中:R1
、R2
及R3
係如式(I)中所定義者,先決條件為:R1
、R2
及R3
係構造上互異的;R6
為(C1
-C6
)烷基,以(C1
-C4
)烷基較佳;其他各種代號係如式(I)中所定義者;且在標記為1之碳原子的立體化學構型係如式(I)中所定義者;而標記為2及1*之碳原子的立體化學各為(R)或(S)構型或彼等之混合物,亦包括消旋構型(R,S),較佳的是,該消旋構型或過量之(R)或(S)構型係佔(R)及(S)構型之總量的60至100%,尤其為70至100%,最佳為80至100%。
本發明之第四個較佳體系係關於其中標記為1之碳原子為對掌性而標記為2及1*的碳原子皆為非對掌性之具旋光性的式(I)化合物或其鹽類;式中:R1
、R2
及R3
係如式(I)中所定義者,先決條件為:R1
、R2
及R3
中至少有二者係構造上相同的;R6
為H;其他各種代號係如式(I)中所定義者;而在標記為1之位置上的立體化學構型係如式(I)中所定義者。
亦為較佳者係通式(Id)及(Ie)所示的化合物,彼等為通式(Ia)化合物的立體異構物,其中在標記為1*之碳原子上的構型係明確界定的(R)或(S):
式中:R1
為(C1
-C6
)烷基、(C1
-C6
)鹵烷基或(C3
-C6
)環烷基,宜為(C1
-C4
)烷基、(C1
-C4
)鹵烷基或(C3
-C6
)環烷基;R2
為H;R3
為鹵素;且其他各種代號係如式(I)中所定義者。
亦為較佳者係式(If)、(Ig)、(Ih)及(Ii)之化合物,彼等為通式(Ic)化合物的立體異構物,其中在標記為1、2及1*之碳原子上的構型係明確界定的:
式中:R1
為(C1
-C6
)烷基、(C1
-C6
)鹵烷基或(C3
-C6
)環烷基;R2
為H;R3
為(C1
-C4
)烷基或鹵素;R6
為(C1
-C6
)烷基;且其他各種代號係如式(I)中所定義者;先決條件為:R1
、R2
及R3
係構造上互異的。
更佳者係具有下列定義之式(If)、(Ig)、(Ih)及(Ii)化合物:R1
為甲基或乙基;R2
為H;R3
為甲基、乙基、F或Cl;R4
及R5
各為H;R6
為甲基或乙基;且R7
、R8
、R9
及R10
各自獨立為H、甲基、Br
、Cl或F;先決條件為:R1
、R2
及R3
係構造上互異的。
亦為較佳者係具有下列定義之式(Id)及(Ie)化合物:R1
為甲基或乙基;R2
為H;R3
為甲基、乙基、F或Cl;R4
及R5
各為H;且R7
、R8
、R9
及R10
各自獨立為H、甲基、Br、Cl或F;先決條件為:R1
、R2
及R3
係構造上互異的。
式(Ij)化合物亦為較佳的化合物,該化合物係通式(Ib)化合物的立體異構物,其中,在標記為1及2之碳原子上的構型係明確界定的:
式中:R1
為H、(C1
-C3
)烷基或(C1
-C3
)烷氧基;或是R1
及R2
可與所連接的碳原子一起形成(C3
-C6
)環烷基環;R2
為H或(C1
-C3
)烷基;R3
為H、鹵素或(C1
-C3
)烷基;R6
為(C1
-C6
)烷基;且其他各種代號係如式(I)中所定義者;先決條件為:R1
、R2
及R3
中至少有二者係構造上相同的。
具有下列定義的式(Ij)化合物亦為較佳的化合物:R1
為H、甲基、乙基、甲氧基或Cl;R2
為H或甲基;或是R1
及R2
可與所連接的碳原子一起形成環丙基環;R3
為H、甲基、F或Cl;R4
及R5
各為H;R6
為甲基;且R7
、R8
、R9
及R10
各自獨立選自H、甲基、Br、Cl或F。
式(If)及(Ih)化合物乃特別較佳的化合物。
式(If)化合物乃最佳的化合物。
另一較佳的化合物族群為式(Ia)、(Ib)、(Ic)、(Id)、(Ie)、(If)、(Ig)、(Ih)、(Ii)或(Ij)化合物,其中R1
、R2
、R3
、R4
、R5
、R6
、R7
、R8
、R9
、R10
及A係如式(I)中之較佳定義所界定者。
一特別較佳的化合物組群為具有下列定義之式(If)化合物:R1
為(C1
-C2
)烷基;R2
為H;R3
為(C1
-C2
)烷基、Cl或F;R4
及R5
各為H;R6
為(C1
-C2
)烷基;R7
、R8
、R9
及R10
各自獨立為H、甲基、F或Cl;且A為CH2
、O或直接鍵(更佳的是,A為直接鍵);先決條件為:R1
、R2
及R3
乃構造上互異的。
式(Ia-1)、(Ic-1)、(Id-1)、(Ie-1)、(If-1)、(Ig-1)、(Ih-1)、(Ii-1)及(Ij-1)化合物(如下文之表前的標題結構式所示者)亦為較佳的化合物,其中R4
及R5
各為H,而R1
、R2
、R3
、R6
、R7
、R8
、R9
、R10
及A係如前文之各基本通式(Ia)、(Ic)、(Id)、(Ie)、(If)、(Ig)、(Ih)、(Ii)及(Ij)中所定義者。
更佳之化合物為具有下列定義之式(Ia-1)、(Id-1)及(Ie-1)化合物(如下文之表前標題結構式所示者):R1
為(C1
-C6
)烷基;R2
為H;R3
為(C1
-C6
)烷基或鹵素;R4
及R5
各為H;R6
為H;且R7
、R8
、R9
及R10
各自獨立為H、(C1
-C6
)烷基或鹵素;先決條件為:R1
、R2
及R3
係構造上互異的。
具有下列定義之式(Ic-1)、(If-1)、(Ig-1)、(Ih-1)及(Ii一1)化合物(如下文之表前的標題結構式所示者)亦為更佳的化合物:R1
為(C1
-C6
)烷基;R2
為H;R3
為(C1
-C6
)烷基或鹵素;R4
及R5
各為H;R6
為(C1
-C6
)烷基;且R7
、R8
、R9
及R10
各自獨立為H、(C1
-C6
)烷基或鹵素;先決條件為:R1
、R2
及R3
係構造上互異的。
具有下列定義之式(Ij-1)化合物(如下文之表前的標題結構式所示者)亦為更佳的化合物:R1
為H、甲基、乙基、甲氧基或Cl;R2
為H或甲基;或是CR1
R2
為環丙基;R3
為H、甲基、Cl或F;R4
及R5
各為H;R6
為甲基;且R7
、R8
、R9
及R10
各自獨立為H、(C1
-C6
)烷基或鹵素;先決條件為:R1
、R2
及R3
中至少有二者係構造上相同的。
式(Ik)、(IL)、(Im)、(In)及(Ip)所示之化合物(如下文之表前的標題結構式所示者)亦為較佳的化合物,其中基團R1
至R10
及A係如對應通式之較佳定義中所界定者。
更佳之化合物為具有下列定義之式(Ik)化合物(如下文之表前的標題結構式所示者):R1
為H、(C1
-C6
)烷基、鹵素或(C1
-C6
)烷氧基;R2
為H或(C1
-C6
)烷基;或是CR1
R2
為環烷基;R3
為H、(C1
-C6
)烷基或鹵素;R4
及R5
各為H;R6
為H;R7
、R8
、R9
及R10
各自獨立為H、(C1
-C6
)烷基或鹵素;且R1
、R2
及R3
中至少有二者係構造上相同的。
具有下列定義之式(IL)、(Im)、(In)及(Ip)化合物(如下文之表前的標題結構式所示者):R1
為(C1
-C6
)烷基;R2
為H;R3
為鹵素;R4
及R5
各為H;R6
為(C1
-C6
)烷基;R7
、R8
、R9
及R10
各自獨立為H、(C1
-C6
)烷基或鹵素。
較佳的式(I)化合物為式(I)所示之具旋光性的氫茚基胺基-1,3,5-三嗪衍生物(A=直接鍵)。同樣亦為較佳之化合物者為式(I)所示之具旋光性的-4-基胺基-1,3,5-三嗪衍生物(A=氧原子)以及式(I)所示之具旋光性的四氫萘基胺基-1,3,5-三嗪衍生物(A=亞甲基)。
前文所述之式(I)化合物可藉由直接應用已知方法或使用經過改造的已知方法(所謂已知方法,亦即,習用或文獻中所記載的方法),例如,如WO 97/31904或WO 97/29095以及本文所引用的參考資料中概括性記載者,以及如下文所記載者。
在下面的敘述中,即使結構式中所出現的代號未明確界定,彼等想當然地係「如前文所定義者」(根據說明書中各代號的第一個定義),或是較佳地,係為所提到的較佳定義。
在下面之方法的敘述所提到的反應順序相當然地可依不同的次序來進行,且可能需要使用適當的保護基來獲得所企求的化合物。
依據本發明的特徵之一,式(I)化合物可藉令式(II)化合物與式(III)之二胍化合物或其酸加成鹽反應,而製得:
式中,R1
、R2
及R3
係如式(I)中所定義,且Z係選自羧酸酯、羧酸正酯、羧酸氯、羧醯胺、氰基、羧酸酐或三氯甲基的官能基,
式中,R4
、R5
、R6
、R7
、R8
、R9
、R10
及A以及在標記為1之位置上的構型係如式(I)中所定義者。該反應通常係在鹼存在下、於惰性溶劑中(諸如,四氫呋喃、二噁烷、乙腈、N,N-二甲基甲醯胺、甲醇或乙醇)、於0℃至溶劑之回流溫度之間的溫度下(宜為20℃至60℃)進行。該鹼通常為鹼金屬氫氧化物、鹼金屬氯化物、鹼金屬碳酸鹽、鹼金屬烷氧化物、鹼土金屬碳酸鹽、或為有機鹼類(諸如,三級胺,例如,三乙胺、或1,8-二氮雜二環[5.4.0]十一碳-7-烯(DBU))。
根據本發明之另一特徵,該式(I)化合物亦可藉令通式(IV)之化合物與式(V)之化合物或其酸加成鹽反應,而製得:
式中,R1
、R2
、R3
、R4
及R5
以及在標記為1*之位置上的構型係如式(I)中所定義者,且L1
為離去基(諸如,氯、三氯甲基、(C1
-C4
)-烷基磺醯基、苯磺醯基或(C1
-C4
)烷基-苯磺醯基),
式中,R6
、R7
、R8
、R9
、R10
及A以及在標記為1之位置上的構型係如式(I)中所定義者。該反應通常係在鹼存在下、於惰性溶劑(例如,極性有機溶劑,如,四氫呋喃、二噁烷、乙腈、N,N-二甲基甲醯胺、甲醇或乙醇)、於0℃至溶劑之回流溫度之間的溫度下(宜為20℃至100℃)進行。該鹼通常為鹼金屬氫氧化物、鹼金屬氫化物、鹼金屬碳酸鹽、鹼金屬烷氧化物、鹼土金屬碳酸鹽、或為有機鹼(諸如,三級胺類,例如,三乙胺或1,8-氮雜二環[5.4.0]十一碳-7-烯(DBU))。
以一般性的籠統用語而言,前述方法係已知者,例如,可見及Comprehensive Heterocyclic Chemistry,A.R. Katritzky and C.W. Rees,Pergamon Press,Oxford,New York,1984,Vol. 3;Part 2B;ISBN 0-08-030703,S. 482。
根據本發明之另一特徵,當式(I)中的R4
與R5
之中有一者為(C1
-C4
)烷基、(C1
-C4
)鹵烷基、(C3
-C4
)烯基、(C3
-C4
)鹵烯基、(C3
-C4
)炔基或(C3
-C4
)鹵炔基時,式(I)化合物可藉令對應式(I)化合物(其中,前述R4
或R5
各別為H,且其他之基團以及構型係如式(I)中所定義者)各別與式(VI)或式(VII)之烷化劑反應,而製得:
R4
-L (VI) R5
-L2
(VII)
式中,L2
為離去基,通常為鹵素(宜為氯、溴或碘)、或是烷基-或苯基磺醯氧基基團(諸如,甲基磺醯氧基或4-甲苯磺醯氧基)。該反應通常係於惰性溶劑中(諸如,四氫呋喃、二噁烷、乙腈或N,N-二甲基甲醯胺)、於0℃至溶劑之回流溫度之間的溫度下(宜為20℃至100℃)進行。
依據本發明之另一特徵,其中之R4
或R5
為醯基的式(I)化合物可藉令對應之式(I)化合物(其中之R4
或R5
各別為H且其他的基團及構型係如式(I)中所定義者)各別與式(VIII)或式(IX)之醯化劑反應,或是與甲醯化劑(諸如,甲酸-乙酸酐)反應,而製得:
R4
-L3
(VIII)R5
-L3
(IX)
式中,R4
及R5
各為如式(I)中所定義的醯基基團,且L3
為離去基(通常為鹵素,以氯較佳)。在醯化反應中,鹼的使用係非強制性的,而該鹼通常係選自鹼金屬氫氧化物、鹼金屬氫化物、鹼金屬碳酸鹽、鹼金屬烷氧化物、或為有機鹼類(諸如,三級胺類,例如,三乙胺)。該反應通常係於惰性溶劑中(諸如,四氫呋喃、二噁烷、乙腈或N,N-二甲基甲醯胺)、於0℃至溶劑之回流溫度之間的溫度下(宜為20℃至100℃)進行。
式(III)之中間物可藉由式(X)化合物與前述式(V)化合物反應而得:
該反應通常係藉由採用式(X)化合物的酸加成鹽(例如,氫氯酸鹽)、在溶劑中(諸如,1,2-二氯苯、十氫萘或白礦油)、於20℃至溶劑之回流溫度之間的溫度下(宜為50℃至200℃)進行。
式(V)之中間物可藉由已知的方法製得,例如,藉由式(XI)之酮類或對應之肟的還原胺化反應(任意之不對稱還原胺化反應):
(式中,R6
、R7
、R8
、R9
、R10
及A係如式(I)中所定義者),或是根據已知的程序,例如,專利公開案WO 97/031904所記載者,令式(XII)化合物與氨或其鹽類反應而製得:
式中,R6
、R7
、R8
、R9
、R10
及A係如式(I)中所定義者且L4
為離去基(諸如,鹵素、羥基、甲基磺醯氧基或4-甲苯磺醯氧基)。
就其中有一或多個不對稱碳以單一鏡像異構形式存在之式(I)化合物的製備而言,前述方法程序可藉由採用式(II)、(III)、(IV)、(V)、(VI)、(VII)或(XII)化合物之適當鏡像異構或非鏡像異構形式,予以調適。呈鏡像異構純形式的式(II)化合物係已知的或是可依據已知的方法程序製備得,例如,Tetrahedron Asymetry 1994,5,981,J. Chem. Soc. Perkin Trans I,1079,2248以及彼等所引証之文獻中所記載者。
呈解析形式或部分解析形式之式(I)化合物的製備可藉由,例如,依照前文所界定的方法,採用一或多種構型與所要製備之式(I)化合物者不同的中間物(II)、(III)、(IV)或(V),並依據已知的解析方法,對所得到的混合物進行解析。
通常係可使用慣用的方法來進行光學解析(參考Textbooks of Stereochemistry),例如,依循將混合物分離為非鏡像異構物的方法,例如,物理方法(諸如,結晶法)、層析法(尤指層柱層析法及高壓液體層析法)、蒸餾法(視需要,在減壓下進行)、萃取及其他方法。通常可藉由在對稱固體相所進行的層析分離法,分離剩餘的鏡像異構物混合物。適用於製備量或適用於工業規模者為諸如對非鏡像異構鹽類進行晶化的方法,該非鏡像異構鹽類可以式(I)化合物為起始物,採用具旋光性的酸類以及,視需要,當有酸基存在時,採用具旋光性的鹼類,製備而得。
適用於藉非鏡像異構鹽類之晶化所進行之光學解析的具旋光性酸類為,例如,樟腦磺酸、樟腦二酸、溴基樟腦磺酸、奎寧酸、酒石酸、二苄醯基酒石酸以及其他類似的酸類;適當之具旋光性鹼類為,例如,奎寧、辛可寧(cinchonine)、乙型奎寧、番木鰲鹼(brucine)、1-苯基乙基胺以及其他類似鹼類。
然後,在大多數的情況下,晶化係在水性或水性-有機溶劑中進行的,在彼等溶劑中,較不溶的非鏡像異構物會先沉澱析出(視情況,在撥種之後沉澱析出)。然後,藉由酸化或使用鹼,式(I)化合物之一鏡像異構物會自該沉澱的鹽釋離出,或是其他的會自晶體釋離出。
式(V)所示之鏡像異構上純的胺中間物可藉由已知的方法製備得,例如,Houben-Weyl,Methoden der Organischen Chemie,4. Auflage,Band E 21b,1833 ff. or Brand E 21e,5133所記載者。較佳的方法程序之一係以不對稱催化作用,對式(XI)同類所進行的還原性胺化反應(包括媒觸轉胺反應)。另一製備式(V)所示鏡像異構上純的胺類的方法程序為消旋物裂解方法(J. Prakt. Chem. 339,(1997),pages 381-384所記載者)或是Org. Lett. ,Vol. 3,Nr. 25,page 4101所記載的方法。在該程序中,係用醯化劑(諸如,任意經取代的脂肪酸酯,宜為氯乙酸甲酯或氯乙酸乙酯或甲氧基乙酸甲酯或甲氧乙酸乙酯),在無機酸存在下,將通式(V)所示之消旋胺鏡像異構選擇性地醯化。然後,藉由用無機酸所進行的簡單處理,將未醯化的鏡像異構物分離出來。接著,使用鹼(例如,鹼金屬氫氧化物,諸如,氫氧化鈉)或酸(例如,無機酸,諸如,氯化氫),將醯化的胺鏡像異構物裂解回對應的胺。就此目的而言,特別適合的是脂酶(生物觸媒),例如,洋蔥假單胞菌(Pseudomonas cepacia)、柱狀念球菌(Candida cyclindracea)或是南極念球菌(Candida antarctica)。此等脂酶中有些亦可自市面上購得(呈固定化形式)(商品名:”Novozym 435”)。
由前述酶促醯化方法類推,理論上,式(XIII)或(XIV)之化合物可藉由醯化與式(V)化合物對應之消旋胺類,以中間物的形式製備得,
式中,R6
、R7
、R8
、R9
、R10
及A係如式(I)中所定義者,且R11
為醯基,宜為(C1
-C6
)烷醯基(其係未經取代或經一或多個選自下列的基團所取代:鹵素、(C1
-C4
)烷氧基及(C1
-C4
)烷硫基),更佳者為甲醯基、乙醯基、丙醯基、鹵基乙醯基、鹵基丙醯基、(C1
-C4
)烷氧乙醯基或(C1
-C4
)烷氧丙醯基,最佳者為氯乙醯基或甲氧乙醯基:然後,藉由使用無機酸或直接使用未醯化的胺(V)(當醯化的化合物(XIV)係以觸媒催化所形成時),將化合物(XIII)裂解,可得到所企求的光學異構物(V)。
例如,下列所述之酸適用於製備式(I)化合物之酸加成鹽類:氫鹵酸類(諸如,氫氯酸或氫溴酸)、磷酸、硝酸、硫酸、單-或二官能基的羧酸以及羥基羧酸類(諸如,乙酸、草酸、順丁烯二酸、琥珀酸、反丁烯二酸、酒石酸、檸檬酸、水楊酸、抗壞血酸或乳酸)、還有磺酸類(諸如,對甲苯磺酸及1,5-萘二磺酸)。式(I)之酸加成化合物可藉由慣用於形成鹽類的方法,以簡單的方式獲得,例如,將式(I)化合物溶解於適當的有機溶劑(諸如,例如,甲醇、丙酮、二氯甲烷或苯),且在0至100℃的溫度下,添加酸,然後,依已知的方式,例如,過濾法,將鹽類單離出,且可視需要用惰性有機溶劑進行清洗,而予以純化。
式(I)之鹼加成鹽類宜在惰性的極性溶劑中(諸如,例如,水、甲醇或丙酮)、於0至100℃的溫度下製備。適用於製備本發明之鹽類的鹼的例子為鹼金屬碳酸鹽類(諸如,碳酸鉀)、鹼金屬及鹼土金屬氫氧化物(例如,NaOH或KOH)、鹼金屬及鹼土金屬氫化物(例如,NaH)、鹼金屬及鹼土金屬烷氧化物(例如,甲醇鈉、第三丁氧鉀)、或是氨或乙醇胺。四級銨鹽類可藉由,例如,與式[NR'R"R''']+
X-
所示之四級銨鹽類進行鹽交換反應(salt exchange)或縮合反應,而製備得,其中R'、R"及R'''各自獨立為(C1
-C4
)烷基、苯基或苄基且X-
為陰離子,例如,Cl-
或OH-
。
其中有一或多個不對稱碳原子係以單一或富旋光性鏡像異構形式存在之某些式(III)及(V)化合物乃新穎的化合物,因而形成本發明之另一特徵,且可依前文所述地製備得。下列之式(V)胺類係已知者:a)氫茚類:(1R)-1-胺基-氫茚(Chem. Abstracts Registry No. 10277-74-4);(1R)-1-胺基-7-甲氧基-氫茚(Arch. Pharm. 331(1998)59-71);(1R)-1-胺基-7-正丙基-氫茚(Arch. Pharm. 331(1998)59-71);(1R)-1-胺基-7-氰基-氫茚(Arch. Pharm. 331(1998)59-71);b)四氫萘類:(1R)-1-胺基-1,2,3,4-四氫萘(Chem. Abstracts Registry No. 23357-46-2);(1R)-1-胺基-7-甲基-1,2,3,4-四氫萘(WO-98/47877);(1R)-1-胺基-7-甲氧基-1,2,3,4-四氫萘(WO-98/47877);(1R)-1-胺基-7-異丙基-1,2,3,4-四氫萘(WO-98/47877);(1R)-1-胺基-7-第三丁基-1,2,3,4-四氫萘(WO-98/47877);後二個化合物之氫氯酸鹽類(WO-98/47877);(1R)-1-胺基-6,8-二甲基-1,2,3,4-四氫萘(J. of Chromatography 959(2002)75-83);c)色滿類(chromanes):(4R)-1-胺基-色滿(Beilstein Registry No.7687402及/或7687403)。
因此,本發明之另一特徵係關於式(III)或(V)之化合物或彼等之鹽類,其中:R6
為H、(C1
-C6
)烷基或(C1
-C6
)烷氧基;R7
、R8
、R9
及R10
各自獨立為H、(C1
-C4
)烷基、(C1
-C3
)鹵烷基、鹵素、(C1
-C3
)烷氧基、(C1
-C3
)鹵烷氧基或CN;A為CH2
、O或直接鍵;且在標記為1之位置上的立體化學構型係如式(I)中所定義,但不包括具有下列定義之式(V)化合物或彼等之鹽類:
(i)A為直接鍵,R6
、R7
、R8
及R9
各為氫,且R10
為氫、甲氧基、正丙氧基或氰基;或
(ii)A為CH2
,且R6
、R7
、R8
及R10
各為氫,且R9
為氫、甲基、甲氧基、異丙氧基或第三丁基;或是A為CH2
,且R6
、R7
及R9
各為氫,而R8
為甲基且R10
為甲基;或
(iii)A為氧原子,且R6
、R7
、R8
、R9
及R10
各為氫。
式(III)及(V)新穎中間化合物或彼等之鹽類之一較佳族群係具有下列定義的化合物:R6
、R7
及R10
各自獨立為H或甲基;R8
為H、甲基、Cl或F;R9
為H、甲基、Cl、F或Br;且A為直接鍵、CH2
或O;而在標記為1之位置上的立體化學構型係如式(I)中所定義,但是不包括具有下列定義之式(V)化合物或彼等之鹽類:
(i)A為直接鍵,R6
、R7
、R8
及R9
各為氫,且R10
為氫,或是
(ii)A為CH2
,而R6
、R7
、R8
及R10
各為氫,且R9
為氫或甲基,或是
(iii)A為氧原子,且R6
、R7
、R8
、R9
及R10
各為氫。
式(III)或(V)之新穎中間化合物或彼等之鹽類的一更佳族群為具有下列定義之化合物:A為直接鍵,R6
為H或甲基;R7
及R10
為氫;R8
為H、甲基、Cl或F;R9
為甲基、Cl、F或Br;且在標記為1之位置上的立體化學構型係如式(I)中所定義者。
另一較佳化合物族群係式(Va)及(Vb)新穎中間化合物或彼等之鹽類:
式中:R6
為甲基;R7
及R10
各自獨立為H或甲基;R8
為H、甲基、Cl或F;R9
為H、甲基、Cl、F或Br;且A為直接鍵、CH2
或O;而彼等化合物因而形成本發明之另一特徵。
某些可用作為製備具旋光性之式(V)類或式(III)二胍類(其中有一或多個不對稱碳原子係以單一或富旋光性鏡像異構形式存在)的式(XIII)化合物(醯胺類)係新穎的且因而構型本發明之另一特徵,且可如前述地製備。下文之式(XIII)醯化胺類係已知者:a)氫茚類:-(1R)-1-乙醯基胺基-氫茚(Chem. Europe 6(2000)1840-1846);-(1R)-1-甲醯基胺基-氫茚(J. Am. Chem. Soc. 88(1966)2233-2240);-(1R)-1-(三氟乙醯基胺基)-氫茚(J. Med. Chem. 45(2002)5260-5279或US-A-4948395);-(1R)-1-(溴基乙醯基胺基)-氫茚(Biochemistry 1980,2140-2144);-(1R)-1-乙醯基胺基-5-氟基-氫茚(J. Org. Chem. 1999,1774-1775);b)四氫萘類:-(1R)-1-乙醯基胺基-1,2,3,4-四氫萘(J. Org. Chem. 1999,1774-1775或Tetrahedron Lett. 43(2002)5260);-(1R)-1-乙醯基胺基-6-甲氧基-1,2,3,4-四氫萘(J. Org. Chem. 1999);-(1R)-1-乙醯基胺基-5,7-二甲基-1,2,3,4-四氫萘(J. Org. Chem. 1999,1774-1775);-(1R)-1-(氯基乙醯基胺基)-1,2,3,4-四氫萘(Farmaco. ED. Sci. Vol. 26(1971)474-486);-(1R)-1-(三氟乙醯基胺基)-1,2,3,4-四氫萘(US-A-4948395);c)色滿類(chromanes):-(4R)-4-乙醯基胺基-色滿(Org. Lett. 4(2002)1695-1668)。
因此,本發明之另一特徵係式(XIII)所示之新穎化合物或其鹽類,其中R6
為H、(C1
-C6
)烷基或(C1
-C6
)烷氧基;R7
、R8
、R9
及R10
各自獨立為H、(C1
-C4
)烷基、(C1
-C3
)鹵烷基、鹵素、(C1
-C3
)烷氧基、(C1
-C3
)鹵烷氧基或CN;R11
為醯基,宜為(C1
-C6
)烷醯基(其係未經取代或經一或多個選自鹵素、(C1
-C4
)烷氧基及(C1
-C4
)烷硫基的基團所取代),更佳者為甲醯基、乙醯基、丙醯基、鹵乙醯基、鹵丙醯基、(C1
-C4
)烷氧基乙醯基或(C1
-C4
)烷氧基丙醯基,最佳者為氯乙醯基或甲氧基乙醯基;A為CH2
、O或直接鍵;且在標記為1之位置上的立體化學構型係如式(I)中所定義者,但是不包括具有下列定義的式(XIII)化合物或其鹽類:
(i)A為直接鍵,R6
、R7
、R8
、R9
及R10
各為氫,且R11
為甲醯基、乙醯基、三氟乙醯基或溴乙醯基,或A為直接鍵,R6
為甲基;R7
、R8
、R9
及R10
各為氫,且R11
為乙醯基,或A為直接鍵,R6
、R7
、R9
及R10
各為氫,R8
為氟基,且R11
為乙醯基,或是
(ii)A為CH2
,且R6
、R7
、R8
、R9
及R10
各為氫,且R11
為乙醯基、三氟乙醯基或氯乙醯基,或A為CH2
,且R6
、R7
及R9
各為氫,且R8
為甲基,而R10
為甲基,且R11
為乙醯基,或A為CH2
,且R6
、R7
、R9
及R10
各為氫,且R8
為甲氧基,而R11
為乙醯基,或A為CH2
,且R6
為甲基、R7
、R8
、R9
及R10
各為氫,而R11
為乙醯基;或是
(iii)A為氧原子,且R6
、R7
、R8
、R9
及R10
各為氫,且R11
為乙醯基。
式(II)、(IV)、(VI)、(VII)、(VIII)、(IX)、(X)、(XI)及(XII)化合物以及消旋的式(III)及(V)化合物係已知者或式可藉由與已知方法類似的方式製備得。
可藉由前述方法程序合成的式(I)化合物集團可額外地以平行的方式,藉手動、半自動或全自動操作,而製得。在本文中,對反應程序、一般處理或產物或中間物的純化進行自動化操作係可能的。總而言之,其應理當被視為意指記載於例如,下列文獻的程序:S.H. DeWitt,“Annual Reports in Combination Chemistry and Molecular,例Diversity: Automated Synthesis”,Volume 1,published by Escom,1997,pages 69-77。
欲以平行的方式來進行反應及一般處理,可採用一系列市售的裝置,彼等可以既有的形式來使用如,Stem Corporation,Woodrolfe Road,Tollesbury,Essex,CM9 8SE,England或H+P Labortechnik GmbH,Bruckmannring 28,85764 Obserchleissheim German。在進行化合物(I)或製備過程中所得到之中間物的平行純化時,特別可採用層析裝置,例如,購自ISCO,Inc.,4700 Superior Street,Lincolin,NE 68504,USA者。前述裝置實現了可分解或組合之組成單位程序,其中各別步驟係自動化的,但是,在各步驟之間必須進行手動操作。為迴避問題,可藉由採用部分或完全統合的自動化系統,其中問題的自動化組成單位可藉由,例如,機械人來操作。如是之自動化系統可購自,例如,Zymark Corporation,Zymark Center,Hopkinton,MA 01748,USA。
除了前述方法之外,式(I)化合物還可完全或部分藉由固相載承方法來製備。為達到此目的,問題合成法或是配合問題程序之合成法的各個中間物或所有中間係結合至合成樹脂上。固相載承合成法深入地記載於專門文獻中,例如,Barry A. Bunin,“The Combinatiorial Index”,published by Academic Press,1998。固相載承合成法的採用使得一系列文獻上已知的實驗計畫的使用成為可能,彼等可以手動或自動化的方式來進行。例如,「茶包方法(teabag method)」(Houghten,US 4,631,211;Houghten et al.,Proc. Natl. Acad. Sci.,1985,82,5131-5135)可藉由採用IRORI,11149 North Torrey Pines Road,La Jolla,CA 92037,USA的產物,部分自動化。採用,例如,Argonaut Technologies,Inc.,887 Industrial Road,San Carlos, CA 94070,USA或MultiSyn Tech GmbH,Wullener Feld 4,58454 Witten,Germany的裝置,可將固相載承平行合成法成功地自動化。
根據本文所述之方法程序的製備方法所產生的式(I)化合物係呈物質聚集物或物質叢集物(libraries)的形式。因此,本發明主題物亦為式(I)化合物(其含有至少二種式(I)化合物)與彼等之前體的叢集物。
下文之非設限用的實施例係例示式(I)化合物。
A.化學實施例
在下面的實施例中,量(百分比亦同)係基於重量,除非另有說明。溶劑比係基於體積。
旋光性係在標準的條件下(c=1 g/ml,t=25℃),以589 nm波長之偏極光(偏極化的Na-D光)的旋光率測得。溶劑為氯仿,除非另有說明。
2-胺基-4-[(1R)-1-氫茚基胺基]-6-甲基-1,3,5-三嗪(表8,化合物編號8.1)
在90-100℃下,將2-胺基-4-氯基-6-甲基-1,3,5-三嗪(2.2 g,0.015 mol)、R(-)-1-胺基氫茚(2.0 g,0.015 mol)及碳酸鉀(4.6 g,2.2 mol)於N,N-二甲基甲醯胺所形成的混合物攪拌5小時。當反應完成後,於真空下,低於100℃的溫度下,將溶劑蒸發,將所得到的混合物冷卻並添加水。添加乙酸乙酯並分離出有機層,予以乾燥(硫酸鈉)並蒸發。利用層柱層析法(用乙酸乙酯洗提),將所得到的殘留物純化,可得到2-胺基-4-[(1R)-1-氫茚基胺基]-6-甲基-1,3,5-三嗪(3.5 g,產率95%,化合物編號8.1,熔點94-96℃,化學純度>95%,ee 91%(HPLC),旋光度(CHCl3
,c=1):+87.4°)。
2-胺基-4-[(4R)-4-色滿基胺基]-6-[(1R)-1-氟乙基]-1,3,5-三嗪(表1,化合物編號1.20)
a.色滿-4-酮肟
將乙酸鈉(41.53 g,0.506 mol)於水所形成之60℃混合物和色滿-4-酮(25 g,0.169 mol)及羥基胺氫氯化物(20.0 g,0.287 mol)於乙醇所形成之60℃混合物合倂在一起。將所得到的混合物加熱回流90分鐘,然後,予以冷卻及過濾。用水清洗粗製固體,可得到色滿-4-酮肟(27.9g,產率96%),熔點114-117℃,純度95%。
b.4-胺基色滿氫氯化物
在氮氣氛下,將色滿-4-酮肟(27.9 g,0.157 mol)(於乙醇中)添加至雷尼鎳觸媒(Raney-nickel catalyst)(3.0 g)(於乙醇中)。攪拌該混合物並導入氫氣,直至理論量的氫(約3.6 L)被吸收為止。過濾出該觸媒,蒸發溶劑並添加6N氫氯酸溶液(25 ml)。將溶劑蒸發並用乙醚/丙酮(10:1)清洗殘留物,再次進行過濾,可得到4-胺基色滿氫氯化物(18.3 g,產率58%),熔點220-226℃,純度95%。
c.N-[(4R)-4-色滿基]-2-甲氧基乙醯胺
用乙酸乙酯萃取4-胺基色滿氫氯化物(27.8 g,0.15 mol)與含水氫氧化鈉(2N)的混合物,將有機層乾燥(硫酸鈉)並進行蒸發,可得到消旋的4-胺基色滿(14.2 g,0.095 mol)。於該化合物中,添加2-甲氧基乙酸甲酯(10.94 g,0.105 mol)以及在第三丁基甲醚內的2.5 gNovozym 435(Aldrich Corp.),並將該混合物加熱回流2小時。再一次添加Novozym 435(0.5g)且持續加熱直到HPLC顯示反應已完全為止。添加二氯甲烷,過濾出生物觸媒並將有機層乾燥(硫酸鎂)及蒸發。將所得到的殘留物溶於最少量的二氯甲烷,並添加氫氯酸的乙醇溶液(8N),可得到(4S)-4-胺基色滿氫氯化物,將其過濾出並將濾液蒸發,可得到N-[(4R)-4-色滿基]-2-甲氧基乙醯胺(8.2g),熔點109-112℃。
d.(4R)-4-胺基色滿氫氯化物
將前述N-[(4R)-4-色滿基]-2-甲氧基乙醯胺(2.2 g,0.0325 mol)於乙醇(100 ml)所形成的溶液以及濃氫氯酸(30 ml)加熱回流12小時,然後,予以蒸發。將少量的乙酸乙酯添加至所得到的殘留物中並過濾出固體,可得到(4R)-4-胺基色滿氫氯化物(2.3 g),熔點261-263℃,化學純度>95%。
e.(4S)-4-(雙胍基)色滿氫氯化物
在140-150℃的溫度下,將氯化(4R)-3,4-二氫-2H-4-色滿基銨(2.3 g,0.0124 mol)及1-氰基胍(1.04 g,0.0124 mol)於1,3-二氯基苯所形成的均質混合物加熱150分鐘。用甲苯稀釋已冷卻的混合物並進行過濾,可得到呈固體之(4S)-4-(雙胍基)色滿氫氯化物(3.3 g,產率89.4%),純度90%。
f.2-胺基-4-[(4R)-4-色滿基胺基]-6-[(1R)-1-氟基乙基]-1,3,3-三嗪
將甲醇鈉於甲醇所形成之30%溶液(0.7 g,0.75 ml,0.004 mol)添加至(4S)-4-(雙胍基)色滿氫氯化物(1.1 g,0.004 mol)於甲醇所形成之已攪拌過的懸浮液中。然後,在室溫下,添加(2R)-2-氟基丙酸甲酯(1.08 g,0.01 mol),接著添加另外的甲醇鈉30%溶液(1.0 g,1.0 ml,0.006 mol)。於室溫下待了4小時後,將該混合物過濾,將濾液蒸發並將所得到的殘留物溶於乙酸乙酯。將有機相清洗(水)、乾燥(硫酸鈉)及蒸發。利用層柱層析法(用乙酸乙酯:庚烷之7:3混合物洗提),將殘留物純化,可得到2-胺基-4-[(4R)-4-色滿基胺基]-6-[(1R)-1-氟基乙基]-1,3,5-三嗪(0.3 g,產率25%,化合物編號1.20),熔點110-112℃,旋光度(二氯甲烷,c=1):+75.4°,純度98.35%(HPLC,Chiracel OD,250x4.6 mm,洗提劑:正己烷:2-丙醇90:10,0.6 ml/min,停留時間:21.4分鐘)。
實施例A3
2-胺基-4-[(1R,2S)-2-甲基-1-氫茚基胺基]-6-[(1R)-1-氟基乙基]-1,3,5-三嗪(表2,化合物編號2.1)
a.2-甲基-1-氫茚-1-酮肟
在60℃下,攪拌2-甲基-1-氫茚酮(10 g,0.0684 mol)及羥基胺氫氯化物(9.5 g,0.1368 mol)於乙醇所形成的混合物,且添加乙酸鈉(16.8 g,0.2052 mol)於水所形成的溶液。然後,將所得到的混合物加熱回流90分鐘,接著冷卻及過濾出固體。用水清洗所得到的粗製產物且予以過濾,可得到2-甲基-氫茚-1-酮肟(9.9 g,產率81%),熔點82-91℃,純度90%。
b.1-(RS)(+-)-1-胺基-2-甲基氫茚氫氯化物
於氮氣氛下,攪拌前述2-甲基氫茚-1-酮肟(9.5 g,0.0589 mol)以及載於碳上的鈀觸媒(10%,1.0 g)於甲醇及乙酸所形成的混合物。然後,導入氫氣直至理論量的氫被吸收為止。過濾出該觸媒並於真空中蒸發溶劑。添加氫氯酸的乙醇溶液(6N),蒸發溶劑並用乙醚/丙酮混合物(10:1)清洗所得到的殘留物,過濾後,可得到1-(RS)(+-)-1-胺基-2-甲基氫茚氫氯化物(9.7 g,產率85%),熔點241-242℃,純度95%。
c.反式-1-胺基-2-甲基氫茚
將1-(RS)(+-)-1-胺基-2-甲基氫茚氫氯化物(19.7 g,0.1073 mol)與含水的氫氧化鈉(2N)混合在一起並用乙酸乙酯萃取。將有機層乾燥(硫酸鈉)、蒸發並利用層柱層析法(用乙酸乙酯/三乙胺(100:1)洗提),將殘留物純化,可得到下列化合物:
i) 反式-1-胺基-2-甲基氫茚(6.6 g),1
H-NMR(CDCl3
):1.25(3H,d),1.90-2.05(1H,m),2.5(1H,dd),3.05(1H,dd),3.78(1H,d,8,1Hz),7.1-7.3(4H,m);
ii) 反式-1-胺基-2-甲基氫茚及順式-1-胺基-2-甲基氫茚的混合物(2.7 g);以及
iii) 順式-1-胺基-2-甲基氫氫茚(4.0 g),1
H-NMR(CDCl3
):0.95(3H,d),2.40-2.60(2H,m),2.80-2.95(1H,m),4.20(1H,d,6.2 Hz),7.1-7.3(4H,m)。
d.N-[(1R,2S)-2-甲基-2-氫茚基]-2-甲氧基乙醯胺,以及(1S,2R)-1-胺基-2-甲基氫茚氫氯化物
將Novozym 435(Aldrich Corp.,1.0 g)添加至反式-1-胺基-2-甲基氫茚(6.6 g,0.0448 g)與2-甲氧基乙酸甲酯(5.04 g,0.0484 mol)於第三丁基甲基醚所形成的混合物中。將該混合物加熱回流2小時,再加入另一份的Novozym 435(0.5 g)且再持續加熱2小時。將二氯甲烷添加至已冷卻的混合物中並過濾掉生物觸媒。將有機層乾燥(硫酸鈉)、蒸發並將所得到的殘留物溶解於最少量的二氯甲烷中。添加氫氯酸的乙醇溶液(8N)並過濾出固體,可得到(1S,2R)-1-胺基-2-甲基氫茚氫氯化物,而將濾液蒸發,則可得到N-[(1R,2S)-2-甲基-1-氫茚基]-2-甲氧基乙醯胺(5.9g),熔點78-79℃。
e.(1R,2S)-1-胺基-2-甲基氫茚氫氯化物
將濃氫氯酸(8 ml)添加至N-[(1R,2S)-2-甲基-1-氫茚]-2-甲氧基乙醯胺(5.9 g,0.0269 mol)於乙醇及水所形成的溶液中,並將所得到的混合物加熱回流12小時。將溶劑蒸發並添加少量的乙酸乙酯。過濾出為溶解的固體,可得到呈固態之(1R,2S)-1-胺基-2-甲基氫茚氫氯化物(1.0 g),化學純度>95%。
f.(1R,2S)-1-(雙胍基)-2-甲基氫茚單氫氯化物
在140-150℃下,將(1R,2S)-1-胺基-2-甲基氫茚氫氯化物(1.0 g,0.0054 mol)及1-氰基胍(0.46 g,0.0054 mol)於1,3-二氯苯所形成的均質混合物加熱15分鐘。用甲苯稀釋已冷卻的混合物並過濾出固體,可得到呈固體之(1R,2S)-1-(雙胍基)-2-甲基氫茚單氫氯化物(1.1 g,產率67.7%),熔點172-178℃,純度90%。
g.2-胺基-4-[(1R,2S)-2-甲基-1-氫茚基胺基]-6-[(1R)-1-氟基乙基]-1,3,5-三嗪
將甲醇鈉(0.39,0.4 ml,0.0022 mol)於甲醇所形成之30%溶液添加至(1R,2S)-1-(雙胍基)-2-甲基氫茚氫氯化物(0.550 g,0.0021 mol)於甲醇所形成之已攪拌過的懸浮液中。在室溫下,添加(2R)-2-氟基丙酸甲酯(0.55 g,0.0051 mol),接著,添加追加量之甲醇鈉(0.59 g,0.6 ml,0.0033 mol)的30%溶液。在室溫下待了4小時後,對混合物進行過濾,並將濾液蒸發。將所得到的殘留物溶於乙酸乙酯,予以清洗(水)、乾燥(硫酸鈉)及蒸發。利用層柱層析法(用乙酸乙酯:庚烷(7:3)混合物作為洗提劑),將所得到的殘留物純化,可得到2-胺基-4-[(1R,2S)-2-甲基-1-氫茚基胺基]-6-[(1R-1-氟基乙基)-1,3,5-三嗪(0.09g,產率15%,化合物編號2.1),熔點146-150℃,旋光度(氯仿,c=1):+104.4°,純度95.25%(HPLC,Chiralcel OD,250x4.6 mm,洗提劑正己烷:2-丙醇90:10,0.6 ml/分鐘,室溫,17.93分鐘)。
下列表1至14所示之較佳的式(I)化合物亦構成本發明之一部分,且係藉由前述實施例A1、A2及A3或前文所述之通用方法或與彼等類似的方法製得的。
在表中,化合物的結構係以佔優勢的立體化學異構物的結構式表示,除非另有特別說明(例如,對掌化合物的消旋混合物)。
下列的縮寫用於表1至14中:「Me」示甲基,「Et」示乙基,且「Pr」示正丙基。「Cpd」示化合物編號。化合物編號僅供參考用。
在某些表之最後面,就各個表之某些化合物,提供了額外的物理數據。
旋光度係如前述實施例A1至A3所測量及定義者。1
H-NMR光譜係在含氘氯仿中紀錄得的,除非另有說明,化學位移係以ppm表示。使用了下列記號:s=單峰,d=雙峰,t=三峰,m=多重峰。
表1內之物理數據的註解(參照表1內之化合物編號):化合物編號1.1:熔點176-178℃,旋光度+116.7°;化合物編號1.2:旋光度+113.5°;化合物編號1.3:旋光度+112.7°;化合物編號1.11:熔點151-154℃,旋光度+111.1°;化合物編號1.12:熔點68-72℃,旋光度+76.8°;化合物編號1.15:熔點163-165℃,旋光度+70.1°;化合物編號1.20:熔點110-112℃,旋光度+75.4°;化合物編號1.21:熔點127-130℃,旋光度+52.3°;化合物編號1.24:熔點153-155℃,旋光度+82.5°;化合物編號1.28:熔點140-144℃,旋光度+79.9°;化合物編號1.31:熔點99-100℃,旋光度+69.2°;化合物編號1.66:旋光度+112.7°;化合物編號1.67:熔點88-95℃,旋光度+66.5°;化合物編號1.68:熔點145-146℃,旋光度+79.3°;化合物編號1.69:熔點149-150℃,旋光度+84.0°。
表2內之物理數據的註解(參照表2內的化合物編號):化合物編號2.1:熔點146-140℃,旋光度+104。;化合物編號2.11:旋光度+168.9。;化合物編號2.25:熔點68-70℃,旋光度+140.9。;化合物編號2.28:熔點127-128℃,旋光度+49.6。。
表3內之物理數據的註解(參照表3內的化合物編號)化合物編號3.1:熔點149-150℃,旋光度+74.4°;化合物編號3.2:旋光度+113.5°;化合物編號3.11:熔點147-149℃,旋光度84.4°;化合物編號3.15:熔點167-171℃,旋光度+36.5°;化合物編號3.20:熔點183-185℃,旋光度+54.5°;化合物編號3.24:熔點151-152℃,旋光度+71.8°。
表4內之物理數據的註解(參照表4內的化合物編號):化合物編號4.1:熔點146-150℃,旋光度+77.9°。
表7內之物理數據的註解(參照表7內的化合物編號):化合物編號7.1:熔點163.5℃;化合物編號7.2:熔點90-92℃,旋光度+179.4°;化合物編號7.72:熔點58-60℃;化合物編號7.203:旋光度+83.4°;化合物編號7.239:熔點180-183℃,旋光度+153.4°化合物編號7.240:熔點80-83℃;化合物編號7.241:熔點50-52℃,旋光度+109.6°;化合物編號7.242:旋光度+116.2°;化合物編號7.243:熔點64-66℃,旋光度+135.0°;化合物編號7.244:熔點72-76℃。
表8內物理數據的註解(參照表8內的化合物編號):化合物編號8.1:熔點94-96℃,旋光度+87.4°;化合物編號8.2:熔點100-102℃;化合物編號8.3:熔點87-89℃,旋光度+97.2°;化合物編號8.11:旋光度+78.7°;化合物編號8.12:熔點95-98℃,旋光度+73.5°;化合物編號8.15:熔點100-103℃,旋光度+92.1°;化合物編號8.21:熔點95-97℃,旋光度+44.3°;化合物編號8.24:熔點65-70℃,旋光度+95.7°;化合物編號8.26:熔點77-78℃,旋光度+80.0°;化合物編號8.34:旋光度+98.5°;化合物編號8.35:熔點77-80℃,旋光度+79.3°;化合物編號8.38:熔點172-174℃;化合物編號8.44:熔點75-79℃,旋光度+56.3°;化合物編號8.49:熔點138-139℃,旋光度+122.1°;化合物編號8.58:熔點135-138℃,旋光度+69.0。
;化合物編號8.61:熔點178-180℃;化合物編號8.67:熔點83-84℃;化合物編號8.68:熔點67-68℃,旋光度+74.2。
;化合物編號8.71:熔點73-75℃,旋光度+77.7。
;化合物編號8.75:熔點75-78℃,旋光度+59.4。
;化合物編號8.79:熔點149-151℃;化合物編號8.90:熔點163-165℃,旋光度+91.6。
;化合物編號8.100:熔點114-117℃,旋光度+94.1。
;化合物編號8.113:熔點63-68℃,旋光度+77.6。
;化合物編號8.117:旋光度+64.0。
;化合物編號8.152:旋光度+75.3。
;化合物編號8.160:熔點70-75℃,旋光度+75.0;化合物編號8.195:熔點125-126℃,旋光度+87.7℃;化合物編號8.196:熔點87-89℃;化合物編號8.197:熔點87-89℃,旋光度+68.8。
;化合物編號8.205:熔點165-167℃;化合物編號8.206:熔點87-90℃,旋光度+60.5。
;化合物編號8.209:熔點90-93℃;化合物編號8.215:熔點100-108℃,旋光度+42.0。
;化合物編號8.219:熔點136-138℃;化合物編號8.231:熔點70-75℃,旋光度+49.3°;化合物編號8.233:熔點148-155℃,旋光度+86.9°;化合物編號8.234:熔點135-140℃,旋光度+81.8°;化合物編號8.237:熔點87-95℃,旋光度+68.0°;化合物編號8.239:旋光度+52.7℃;化合物編號8.240:熔點87-88℃,旋光度+55.5°;化合物編號8.243:旋光度+63.0°;化合物編號8.245:熔點136-139℃,旋光度+66.7°;化合物編號8.246:熔點73-75℃,旋光度+75.0°;化合物編號8.247:熔點63-70℃,旋光度+75.0°;化合物編號8.248:熔點63-70℃,旋光度+71.2°;化合物編號8.252:熔點70-75℃;化合物編號8.254:熔點170-173℃,旋光度+109.6°;化合物編號8.256:熔點72-76℃;化合物編號8.257:熔點63-65℃;在下面的表9至14中,詳記了一或多個對掌中心的立體化學,而在表實施例中,1R位置上的光學純度則當然為至少90%。
表10內之物理數據的註解(參照表10內的化合物編號):化合物編號10.1:溶點147-151℃,旋光度+91.5°;化合物編號10.2:熔點92-94℃;化合物編號10.37:熔點82.84℃;化合物編號10.38:熔點76-77℃;化合物編號10.47:熔點85-88℃;化合物編號10.57:熔點90-93℃;化合物編號10.67:熔點80-85℃;化合物編號10.68:熔點90-93℃,旋光度+77.0°;
下面的表15例示通示(V)所示之中間物,彼等係用來製備前述式(Ia-1)、(Ib)、(Ic)、(Ic-1)、(Id)、(Id-1)、(Ie)、(Ie-1)、(Ik)、(In)及(Ip)化合物。就其中之R6
為甲基的化合物而言,在標記為2之碳原子上的構型為消旋,亦即(2RS)。
表15內之參閱符號的註解:(a)1
H-NMR(DMSO)8.8(br,3H),7.5(m,1H),7.3(m,1H),7.1(m,1H),4.7(m,1H),3.0(m,1H),2.8(m,1H),2.5(m,1H),2.0(m,1H);(b)7.14(s,1H),6.98(s,1H),4.30(t,1H),2.87(ddd,1H),2.72(m,1H),2.45(m,1H),2,25(s,3H),2.24(s,3H),1.62(m,1H);(c)7.03(d,1H),6.99(d,1H),4.50(dd,1H),3.12(m,1H),2.79(ddd,1H),2.38(m,1H),2.30(s,3H),2.25(s,3H),1.88(m,1H);(d)7.12(d,1H),6.83(d,1H),4.30(t,1H),2.90(ddd,1H),2.75(m,1H),2.50(m,1H),2.24(s,3H),1.64(m,1H);(e)(DMSO)8.5(br,3H),7.4(s,1H),7.1(m,2H),4.3(t,1H),2.7(m,2H),2.25(s,3H),2.1-1.6(m,4H);(f)(DMSO)8.4(br,3H),7.15(s,1H),6.95(s,1H),4.3(br,1H),2.5(m,2H),2.25(s,3H),2.15(s,3H),2.0-1.6(m,4H);(g)(DMSO)8.8(br,3H),7.4(d,1H),7.05(dd,1H),6.75(d,1H),4.4(br,1H),4.2(m,2H),2.25(s,3H),2.3-2.0(m,2H);(h)(DMSO)8.6(br,3H),7.5(s,1H),7.2(dd,2H),4.7(t,1H),3.0(m,1H),2.8(m,1H),2.6(q,2H),2.5(m,1H),2.0(m,1H),1.2(t,3H);(i)(DMSO)8.9(br,3H),7.4(d,1H),7.2(m,1H),6.95(m,1H),4.5(t,1H),4.3(m,2H),2.4-2.1(m,2H);(j)(DMSO)8.7(br,3H),7.3(d,1H),6.75(d,1H),4.4(t,1H),4.3(m,2H),2.2(s,3H),2.3-2.1(m,2H),2.0(s,3H)。
下面的表16例示前述通式(Va)所示之中間胺類,彼等係用來製備前述式(If)、(If-1)、(Ig)、(Ig-1)、(Ij)、(Ij-1)及(IL)化合物。
表16內之參閱符號的註解:(a) (DMSO)8.8(br,3H),7.7(d,1H),7.3(m,3H),4.3(br,1H),3.2(m,1H),2.5(m,2H),1.2(d,3H);(b) (DMSO)8.8(br,3H),7.4(s,1H),7.15(m,2H),4.2(br,1H),3.2(m,1H),2.5(m,2H),2.3(s,3H),1.2(d,3H);(c) (DMSO)8.5(br,3H),7.6(dd,1H),7.2(m,3H),4.1(br,1H),2.8(m,1H),2.2(m,1H),2.0(m,1H),1.5(m,1H),1.1(d,3H)。
下面的表17例示前述通式(Vb)所示之中間胺類,彼等係用來製備前述式(Ih)、(Ih-1)、(Ii)、(Ii-1)及(Im)化合物。
表18及19:式(XIII)化合物
式中R11
為氯乙醯基[化合物編號18.1至18.63]或甲氧乙醯基[化合物編號19.1至19.63],且在其中之R6
為甲基之化合物的情況下,在標記為2之碳原子上的構型為消旋,亦即(2RS)。
表20及21:式(XIIIa)化合物
式中,R11
為氯乙醯基[化合物編號20.1至20.30]或甲氧乙醯基[化合物編號21.1至21.30]
表22及23:式(XIIIb)化合物
式中,R11
為氯乙醯基[化合物編號22.1至22.30]或甲氧乙醯基[化合物編號23.1至23.30]
本發明之另一特徵係提供用作除草劑和植物生長調節劑的用途,其特徵係在於將可有效控制雜草或調節植物生長之量的式(I)化合物或其鹽類,施用於植物所在地。就此目的而言,前述化合物通常係以除草組成物的形式(亦即,與相容的稀釋劑或載體及/或適用於除草組成物之表面活性劑聯合在一起),來使用,例如,下文所述者。
所謂施用於「植物所在地」係指,例如,施用於植物生長介質,諸如,土壤,還有種子、出土的幼苗、根、莖、葉或其他植物部分。
式(I)化合物及彼等之鹽類(在下文中皆簡稱為式(I)化合物)具有極佳的除草活性,以對抗廣範圍之在經濟上具重要性的單子葉及雙子葉有害植物。式(I)化合物亦可有效地作用於多年生雜草,其自種子或地下莖、根莖或其他多年生器官產生嫩枝且難以控制。在本文中,該化合物不論在種植前、萌前或萌後,皆可施用。可被式(I)化合物所控制之某些具代表性單子葉及雙子葉植物區系的例子係如下所述,但是下文之列舉非為對於某些雜草屬類的限制。
在單子葉雜草屬中,可被活性化合物有效控制者為,例如,在一年生的雜草中有:翦股穎屬、看麥娘屬、Apera、水楊梅屬、背形草屬、雀麥屬、指梳茅屬、指草屬、野稗屬、荸薺屬、穇屬、羊茅屬、飄拂草屬、鴨嘴草屬、黑麥草屬、壓舌草屬、匍黍屬、雀稗屬、金絲雀草屬、梯牧草屬、早熟禾屬、慈菇屬、螢藺屬、狗尾草屬、尖瓣花屬以及莎草屬;而在多年生的雜草中有:鵝觀草屬、狗牙根屬、白茅屬以及高梁屬,還有多年生的莎草屬。
在雙子葉雜草屬的情況下,作用譜擴展至,諸如,例如,在一年生中有:豬殃殃屬、堇菜屬、婆婆納屬、芫麻屬、繁縷屬、莧屬、芥屬、薯屬、母菊屬、苣蔴屬及金時花屬,而多年生的雜草有:旋花屬、薊屬、殼菜屬及黃花蒿屬。
在諸如下列之雙子葉有害植物的情況下,亦可達到除草作用:豚草屬、黃春菊屬、薊屬、矢車菊屬、藜屬、曼陀羅屬、Emex、黃鼬瓣花屬、小米菊屬、地膚屬、獨行菜屬、母草屬、罌粟屬、馬齒莧屬、蓼屬、毛良屬、葶藶屬、水松葉屬、千里光屬、菁屬、茄屬、苣實屬、蒲公英屬、三葉草屬、蕁麻屬及蒼耳屬。
發生在稻米之特定耕作條件下的有害植物為,諸如,例如,慈菇屬、澤瀉屬、荸薺屬、莞屬及莎草屬,亦可被依據本發明之化合物控制得極佳。
若本發明之化合物係在發芽前(雜草的萌前)施用至土壤表面,則可完全防止雜草幼苗的出土,或是雜草只會生長到子葉的階段,然後即停止生長且最後,在經過三至四星期後,會完全死亡。
當本發明之化合物係在萌後施用至植物的綠色部分(green part),則在施用後的非常短時間內,生長會徹底地停止且雜草植物會停留在施用時點的發育階段,或是在某段時間後(多少有些快速),彼等雜草會完全死亡,因此,依此方式,對於農作物有害之雜草的競爭會在非常早期的時點且以緩釋的方式被除去。
雖然依據本發明之化合物對於雙子葉及單子葉植物具有極佳的除草活性,但是,若施藥的劑量適當,則對於具有經濟價值的農作物,諸如,例如,小麥、大麥、裸麥、黑小麥、稻米、玉米、甜菜、棉花或大豆(尤指小麥、大麥、稻米或玉米)僅有不顯著程度的損害或完全沒有損害。基於此等理由,本發明之化合物在某些情況下,適用於選擇性控制農業上有用之植物群叢或觀賞用植物群叢中的非所欲之植物。
前述活性使得本發明之化合物可作為有效的除草活性成分,以相對較低的劑量,以選擇性除草劑的形式用於某些作物(在多數情況下,宜為雜草的萌前階段),在萌前及萌後用於控制闊葉雜草及禾本科雜草。另外,本發明之化合物可在較高的劑量下,藉由特地的施用技術,有效地用於控制種植農作物之廣範圍雙子葉雜草及單子葉雜草,亦可用於農業行間作物(諸如,玉米、棉花等等)之行間處理。
依據本發明之組成物可用於選擇性地控制種植作物(諸如,油椰、椰子樹、印度橡樹、柑桔類、鳳梨、仁果、棉花、咖啡、可可等等),還有水果生產及葡萄栽培之一年生及多年生有害植物。同樣地,根據本發明之組合可用於採用無耕種或零耕種方法之可耕作物生產。
因此,本發明之另一標的係藉由施用作為除草劑之本發明化合物來選擇性控制種植作物之雜草的方法。
另外,本發明之化合物可以非選擇性的方式作為非常有效的除草劑,用於人行道、開放空間以及工業用地等等,使得此等區域免於非所要的植物生長。
依據本發明之除草組成物具有傑出之作用開始快速之長效除草作用。
亦可能使用式(I)化合物與其他具有農藥活性之物質或營養素(諸如,例如,殺蟲劑、殺蟎劑、除草劑、殺菌劑、保護劑、肥料及/或生長調節劑)的組合。
因此,本發明係關於控制非所要之植物生長的方法,其包含將一或多種A類除草劑連同一或多種B類除草劑以及C類界面活性劑施用於有害植物、此等植物之部分或耕作的區域。A類除草劑為式(I)化合物或彼等之鹽類;B類除草劑為可與式(I)化合物倂用以達擴展可控制雜草譜或增加除草效果之目的的除草劑(某些可能使用之B類除草劑說明於下文)。
此外,依據本發明之化合物還對於農作物具有優異的生長調節性質。彼等以調節的方式介入植物的新陳代謝,因此可用於植物組成的標的控制(targeted control)及促進收穫,諸如,例如,引起乾燥以及阻礙生長。此外,彼等亦適用於一般性地控制及抑制非所要的營養生長,而不至於在過程中,損傷農作物。營養生長之抑制在許多單子葉以及雙子葉作物的耕作中,扮演著重要角色,因為倒伏會減少或是因而完全避免。
由於具有除草及植物生長調節性質,式(I)化合物亦可用於控制已知植物或尚待開發之基因改良植物之農作物中的有害植物。一般而言,轉基因的植物係以具有特別有利的性質為特徵,例如,對於某些農藥的抗性(尤指對於某些除草劑的抗性)、對於植物病害或植物病害之致病有機體(諸如,某些害蟲或微生物,例如,真菌、細菌或病毒)的抗性。其他之特性性質係,例如,與收穫產物之品質、量、儲存安定性、組成及特殊成份有關者。因此,澱粉含量增加或澱粉的品質獲改變之轉基因的植物或收穫產物的脂肪酸組成不同之轉基因植物係已知者。
式(I)化合物宜施用於有用及觀賞植物之具經濟價值的轉基因農作物,例如,穀類(諸如,小麥、大麥、裸麥、燕麥、粟、稻米、木薯及玉米)或甜菜、棉花、大豆、油菜、馬鈴薯、蕃茄、豌豆及其他蔬菜類的農作物。式(I)化合物宜作為對於除草劑之植物毒性具有抗性或經基因改良而具有抗性之有用植物農作物的除草劑。
供產生具有改良性質(與既存之植物相較之下)之新穎植物的傳統方式包含,例如,傳統的育種方法及突變種的分生。然而,具有改變性質之新穎植物亦可藉助重組法來產生(參見,例如,EP-A-0221044、EP-A-0131624)。例如,已發表者有下列幾種情形:對農作物植物進行重組改良,以改良植物內所-合成的澱粉(例如,WO 92/11376、WO 92/14827、WO 91/19806),對於下列種類之除草劑具有抗性的轉基因農作物植物:固殺草(glufosinate)類(參見,例如,EP-A-0242236、EP- A-242246)或嘉磷塞(glyphosate)類(WO 92/00377)或磺醯脲類(EP-A-0257993、US-A-5013659),-具有產生蘇力菌毒素(Bt毒素)之能力而賦予植物對抗某些害蟲之抗性的轉基因農作物植物,例如,棉花(EP-A-0142924、EP-A-0193259),-具有改良之脂肪酸組成的轉基因農作物(WO 91/13972)。
在分子生物領域中,有多種可用於製備具有改良性質之新穎轉基因植物的技術在理論上係已知者;參見,例如,Sambrook et al.,Molecular Cloning,A Laboratory Manual,2nd
Ed.,Cold Spring Harbor LabOratory Press,Cold Spring Harbor,NY,或Winnacker“(Genesand Clones]”
,VCH Weinheim 2nd
Edition 1996或Christou,“Trendsin Plant Science” 1(1996)423-431。
為了進行如是之重組操作,可將核酸分子導入細胞質,在細胞質內藉由DNA序列的重組而發生突變或序列的改變。藉助前述標準程序,可能進行,例如,鹼基的交換、部份序列的去除或是天然或合成序列的添加。可將接合子或連接子附接在DNA片段上,以將DNA片段相互連接。
例如,具有基因產物之降低活性的植物細胞可藉由表現至少一個反義RNA、順義RNA以達到共抑制(cosupression)的效果,或是表現至少一個專門裂解前述基因產物之轉錄本的經適當構築的地下莖。
為達該目的,可採用包含了基因產物之全部編碼序列(包括任何可能存在的周圍序列(flanking sequences))的DNA分子,或是採用僅包含了部分編碼基序列的DNA分子(該部分序列必須有足夠的長度,俾能在細胞中產生反義效果)。亦可採用與基因產物之編碼序列具有高度同質性但卻非完全相同的DNA序列。
當核酸分子在植物內表現時,合成出來的但蛋白質可集中於植物細胞內之任何所企求的區間內。然而,為了達到在特定區間內的集中化,例如,可將編碼區域與DNA序列連接以確保在某一特定區間內的集中化。如是之序列係習於此藝之士所熟知的(參見,例如,Braun et al.,EMBO J. 11(1992),3219-3227;Wolter et al.,Proc. Natl. Aca. Sci. USA 85(1988),846-850;Sonnewald et al.,Plant J. 1(1991),95-106)。
採用已知的技術,可在整個植物內再產生出轉基因的植物細胞。該轉基因的植物理論上可為任何所企求的植物種類,即不論是單子葉或雙子葉植物皆可。
這使得可藉由同質(天然)基因或基因序列之過度表現、壓抑或抑制或異質(外來)基因或基因序列之表現,而得到具有改變性質的轉基因植物。
較佳地,式(I)化合物可用於對於選自磺醯脲類、固殺草-銨或嘉磷塞-異丙基銨之除草劑以及類似活性物質具有抗性之轉基因作物。
當將式(I)化合物用於轉基因作物時,除了對於可在其他農作物發現到之有害植物的對抗效果外,還可觀察到施用於成為問題之轉基因農作物時所特有的效果,例如,可被控制之雜草的範圍獲變更或特別地擴大了;可用於施用之噴佈量獲變更;較佳的是,與轉基因農作物所對抗之除草劑的溶混性或可組合性良好;以及對於轉基因農作物植物之生長及產量的影響。
因此,本發明亦關於式(I)化合物作為控制轉基因作物之有害植物的除草劑的用途。
依據本發明之控制有害植物或調節植物生長的用途還包括式(I)化合物在施用於植物後,在植物或土壤類,目前驅體(“前藥”)形成的情況。
式(I)化合物可以可潤濕的散劑、可乳化濃體、可噴灑的溶液、粉劑或粒劑的形式用於習用製劑。
因此,本發明亦關於包含式(I)化合物之除草及植物生長調節組成物。
本發明之另一特徵係在於提供除草或植物生長調節組成物,其包含有效量之如前文所定義之式(I)化合物或其農業上可接受的鹽類,連同較佳之均勻分散於其中的一或多種相容之農業上可接受的溪唑基或載體及/或界面活性劑[亦即,在技藝上通常被接受為適用於除草組成物且與本發明隻化合物相容隻種類的溪式雞或載體及/或界面活性劑]。「均勻地分散」一詞係用來包括式(I)化合物溶於其他組成分所形成的組成物。就廣義而言,「除草組成物」一詞係用來不僅僅包括立即可用作為除草劑的組成物,還包括在使用前必須先稀釋之濃體(包括槽混合物)。
取決於佔優勢之生物及/或化學-物理參數,式(I)化合物可以各種方式來調配。可能之適用製劑的例子有:可潤濕的散劑(WP)、水溶性散劑(SP)、基於油或水的懸浮濃體(SC)、水溶性濃體(SL)、可乳化濃體(EC)、乳劑(EW)(諸如,水包油式及油包水式乳劑)、可噴灑的溶液、懸浮濃體(SC)、油基或水基分散劑、油可溶混的溶液、膠囊懸浮劑(CS)、粉劑(DP)、浸種組成物、供撒播及土壤施用的粒劑、呈微粒劑形式的粒劑(GR)、噴灑粒劑、包衣粒劑及吸附粒劑、水可分散性粒劑(WG)、水溶性粒劑(SG)、ULV製劑、微囊劑及蠟製劑。
此等各別的製劑類型在原理上係已知的且已記載於,例如,Winnacker-Kchler,“Chemische Technologie”[Chemical Technology],Volume 7,C. Hanser Verlag Munich,4th
Edition,1986;Wade van Valkenburg,“Pesticide Formulations”,Marcel Dekker,N.Y.,1973;K. Martens,“Spray Drying” Handbood,3rd
Ed. 1979,G. Goodwin Ltd. London。
必需之調配佐劑,諸如,惰性物質、界面活性劑、溶劑及其他添加劑同樣係為已知者且已記述於,例如,Watkins,“Handbook of Insecticide Dust Diluents and Carriers”,2nd
Ed.,Darland Books;Caldwell N.J.,H.V. Olphen,“Introduction to Clay Colloid Chemistry”,2nd
Ed.,J. Wiley & Sons,N.Y.;C. Mardsen,“Solvents Guid”,2nd
Ed.,Interscience,N.Y. 1963;McCutcheon's “Detergents and Emulsifiers Annual”,MC Publ. COrp.,Ridgewood N.J.;Sisley and Wood,“Encyclopedia of Surface Active Agents”,Chem. Publ. Co. Inc.,N.Y.1964;Schnfeldt,“Grenzflchenaktivethylenoxidaddukte [Surface-Active Ethylene Oxide Adducts]”,Wiss. Verlagsgesell.,Stuttgart 1976;Winnacker-Kchler,“Chemische Technologie”,Volume 7,C. Hanser Verlag Munich,4th
Edition 1986.
基於此等製劑,亦可能製備此等製劑與其他具農藥活性物質(諸如,例如,殺蟲劑、殺滿劑、除草劑、殺菌劑)以及保護劑、肥料及/或生長調劑的倂合物,其例如,係呈現呈混合物或槽混合物的形式。
可潤濕的散劑係均勻分散於水中的製劑且除了式(I)化合物、稀釋劑或惰性物質之外,還含有離子性及/或非離子性的界面活性劑(潤濕劑、分散劑),例如,聚乙氧基化烷基酚類、聚乙氧基化脂肪醇類、聚乙氧基化脂肪胺類、脂肪醇聚乙醇醚硫酸鹽類、烷磺酸類、烷基苯磺酸類、木質素磺酸鹽類、2,2'-二萘基甲烷-6,6'-二磺酸鈉、二丁基萘磺酸鈉或油基甲基胺乙磺酸鈉。為製備可潤濕散劑,式(I)化合物係,例如,於習用的裝置(諸如,錘磨機、扇式研磨機或噴氣式研磨機)中,被磨碎,並同時或依序先後與調配佐劑混合。
可乳化濃體係藉由,例如,下列方法製得:將式(I)化合物溶於有機溶劑中,例如,丁醇、環己酮、二甲基甲醯胺、二甲苯或沸點相對較高的芳族化合物或烴類或有機溶劑的混合物,並添加一或多種離子性及/或非離子性的界面活性劑(乳化劑)。可採用之乳化劑的例子有:烷基芳基磺酸類,諸如,十二碳烷基苯磺酸鈣,或非離子性乳化劑,諸如,烷基芳基聚乙二醇醚(不同於乙氧基化對-烷基酚)、脂肪酸聚乙二醇酯類、脂肪酸聚乙二醇醚類、環氧丙烷-環氧乙烷縮合產物、烷基聚醚類、山梨聚糖酯類(例如,山梨聚糖脂肪酸酯類)或聚氧乙烯山梨聚糖酯類(例如,聚氧乙烯山梨聚糖脂肪酸酯類)。
粉劑係藉由以下方法得到:將活性化合物與細碎的固體物質,例如,滑石、天然石膏(諸如,高嶺土、膨潤土及皂石[pyrophillite])或矽藻土,一同研磨。
懸浮濃體可為水基或油基者。彼等可,例如,藉由使用工業上習用的珠粒式研磨機(bead mills),在有或無添加其他製劑類型部分已提到之界面活性劑的情況下,進行濕式研磨而製得。
乳劑(例如,水包油式乳劑(EW))可,例如,藉助攪拌機、膠體研磨機及/或靜態混合器,使用含水溶劑及視需要使用的界面活性劑(例如,在其他製劑類型部分已提及者)而製得。
粒劑可藉由下列二方法之製得:將式(I)化合物噴灑至吸附性、粒化的惰性物質上;或是藉由黏合劑,例如,糖類(諸如,戊醣及己醣)及礦油類,將該活性化合物塗覆在載體的表面上,諸如,砂、高嶺土或粒化的惰性物質。適當活性化合物亦可依照肥料粒劑製備所習用的方式(視需要,可以與肥料所形成之混合物的形式),進行粒化。
水可分散的粒劑通常係藉由習用的程序,諸如噴霧乾燥法、流化床成粒法、圓盤成粒法、採用高速混合機的混合法以及未使用固體惰性物質的擠壓法。關於圓盤狀、流化床、擠壓及噴霧粒劑的製備,可參見,例如,”Spray-Drying Handbook”3rd
Ed. 1979,G. Goodwin Ltd,London;J.E. Browning,“Agglomeration”,Chemical and Engineering 1967,pages 147 ff.;“Perry's Chemical Engineer's Handbook”,5th
Ed.,McGraw-Hill,New York 1973,pp. 8-57的方法。
作物保護產物之製劑的更進一步詳細資料可參見,例如,G.C. Klingman,“Weed Control as a Science”,John Wiley and Sons,Inc.,New York,1961,pages 81-96 and J.D. Freyer,S.A. Evans,“Weed Control Handbook”,5th
Ed.,Blackwell Scientific Publications,Oxford,1968,pages 101-103。
一般而言,農化製劑包含0.1至99重量%之式(I)活性化合物,尤其為0.1至95重量%。在可潤濕之散劑中,活性物質的濃度為,例如,大約10至90重量%,100重量%之剩餘部份係由習用的製劑組成份所構成。在可乳化濃體的情況下,活性物質的濃度可達到大約1至90重量%,以5至80重量%較佳。呈粉劑形式的製劑通常包含1至30重量%之活性物質,而在大多數的情況下,以5至20重量%較佳;而可噴灑的溶液包含0.05至80重量%活性物質,宜為2至50重量%。在水可分散性粒劑的情況下,活性物質的含量乃部份取決於活性化合物係呈液態或固態並且取決於所使用之粒化助劑、填料等等。在水可分散性粒劑的情況下,例如,活性物質之含量係在1至95重量%之間,宜在10至80重量%之間。
此外,所提及之式(I)化合物的製劑,視需要,可包含增黏劑、潤濕劑、分散劑、乳化劑、滲透劑、防腐劑、防凍劑、溶劑、填料、載體、色料、防泡劑、蒸發抑制劑以及pH及黏度調節劑,彼等在各情況下皆為習用者。
式(I)化合物或彼等之鹽類可以彼等本身的形式或是以彼等與其他具農藥活性物質(諸如,例如,殺蟲劑、殺蟎劑、殺線蟲劑、除草劑、殺菌劑、保護劑、肥料及/或生長調節劑)之倂合物所形成之製劑(調配劑)的形式(例如,預混合物或槽混合物)來使用。
可與本發明之活性物質組合而以混合製劑或槽混合物之形式使用的活性物質為,例如,基於彼等對於,例如,乙醯乳酸合成酶、乙醯基-輔酶A羧酸酶、PS I、PS II、HPPDD、八氫番茄紅素去飽和酶、原卟啉原(protoporphyrinogen)氧化酶、榖胺醯胺合成酶、纖維素生物合成、5-烯醇丙酮醯基莽草酸酶-3-磷酸酯合成酶之抑制作用的已知活性化合物。如是化合物以及其他亦可使用之化合物(彼等之作用機轉在某種程度上係未知或互異的)係記載於,例如,Weed Research 26,441-445(1986)或”The Pesticide Manual”,12th
edition 2000(下文中簡稱為”PM”),The British Crop Protection Council and the Royal Soc. of Chemistry(editors),包括the e-Pesticide Manual Version 2.2(2002)以及其所引用之文獻。可與式(I)化合物倂用且自文獻已知而可提及之除草劑為,例如,下列活性物質(註:彼等化合物係以根據International Organization for Standardization(ISO)所定之俗名或化學名表示,或是,視需要,還加上慣用代號);有俗名之化合物還可參見可得自網際網路之”Compendium of Pesticide Common Names”以及其中所引用的文獻:乙草胺(acetochlor);三氟羧草醯(acifluorfen)(-鈉);阿克龍呢分(aclonifen);AKH 7088,亦即,[[[1-[5-[2-氯基-4-(三氟甲基)-苯氧基]-2-硝基苯基]-2-甲氧基亞乙基]胺基]氧基]乙酸及其甲酯;拉草(alachlor);阿落西頂(alloxydim)(-鈉);草殺淨(ametryn);阿米咔唑(amicarbazone);醯胺基拉草(amidochlor);醯胺基舒福隆(amidosulfuron);草脫淨(amitrol);AMS,亦即,胺基磺酸銨;阿尼羅佛(anilofos);亞速爛(asulam);莠去津(atrazine);草芬定(azafenidin);阿秦舒福隆(azimsulfurone)(DPX-A8947);阿秦普洛碎(aziprotryn);巴般(barban);BAS 516H,亦即,5-氟基-2-苯基-4H-3,1-苯并噁嗪-4-酮;倍伏盧米(beflubutamid);草除靈乙酯(benazolin)(-乙基);倍尼芬(benfluralin);倍伏莎(benfuresate);免速隆(bensulfuron)(-甲基);倍蘇里(bensulide);滅草松(bentazone)(-鈉);倍塞同(benzobicyclone);倍費納(benzofenap);倍若伏(benzofluro);倍若普(benzoylprop)(-乙基);倍塞隆(benzthiazuron);畢拉草(bialaphos,bilanafos);必芬諾(bifenox);必派巴(bispyribac);克草(bromacil);溴布得(bromobutide);溴芬西(bromofenoxim);溴苯腈(bromoxynil);博木隆(bromuron);布納伏(buminafos);布辛酮(busoxinone);丁基拉草(butachlor);布芬希(butafenacil);布明伏(butamifos);丁烯基拉草(butenachlor);布塞宗(buthidazole);比達寧(butralin);拔敵草(butylate);唑草胺(CH-900);卡它明(carbetamide);卡措蹤(cafentrazone)(-乙基)(ICI-A0051);CDAA,亦即,2-氯基-N,N-二-2-丙烯基乙醯胺;CDEC,亦即,二乙基二硫基胺基甲酸2-氯基烯丙基酯;甲氧基護谷(chlomethoxyfen);克攔本(chloramben);克瑞伏(chlorazifop)(-丁基);氯溴隆(chlorbromuron);克布繁(chlorbufam);克芬那(chlorfenac);克芮可-甲基(chlorflurecol-methyl);克達宗(chloridazon);氯嘧黃隆(chlorimuron)(-乙基);全滅草(chlornitrofen);氯麥隆(chlorotoluron);克秀隆(chloroxuron);克普凡(chlorpropham);氯速隆(chlorsulfuron);大克草-二甲基(chlorthal-dimethyl);克塞明(chlorthiamide);克盧隆(chlortoluron);西尼同(cinidon)(-甲基或-乙基);辛沒淋(cinmethylin);西速隆(cinosulfuron);剋草同(clethodim);剋第伏(clodinafop)以及其酯類衍生物(例如,剋第伏-炔丙基);可滅蹤(clomazone);克草普(clomeprop);克普敵(cloproxydim);畢克草(clopyralid);克派舒福隆(clopyrasulfuron)(-甲基);克蘭速爛(cloransulam)(-甲基);庫陸隆(cumyluron)(JC 940);氰乃淨(cyanazine);賽克得(cycloate);賽發隆(cyclosulfamuron)(AC 104);環殺草(cycloxydim);賽陸隆(cycluron);賽伏草(cyhalofop)以及其酯類衍生物(例如,丁基酯,DEH-112);賽沛葵(cyperquat);賽拉秦(cyprazine);賽拉柔(cyprazole);戴木隆(daimuron);2,4-D;2,4-DB;得拉草;邁隆(dazomet);德第凡(desmedipham);德沒翠(desmetryn);地阿拉(di-allate);麥草畏(dicamba);二氯苯(dichlobenil);地克羅普(dichlorprop);地克伏(diclofop)以及其酯類(諸如,地克伏-甲基);地克速爛(diclosulam);地撒提(dithatyl);地芬隆(difenoxuron);野麥枯(difenzoquat);地芬坎(diflufenican);地沒隆(dimefuron);二甲基拉草(dimethachlor);地撒翠(dimethametryn);汰草滅(dimethenamid)(SAN-582H);汰草滅(-P);地沒蹤(dimethazone);穫萎得(dimethipin);地沒西攔(dimexyflam);地速隆(dimetrasulfuron);撻乃安(dinitramine);達諾殺(dinoseb);敵特博(dinoterb);大芬滅(diphenamid);大普翠(dipropetryn);地刈(diquat);汰硫草(dithiopyr);達有龍(diuron);DNOC;依那秦-乙基(eglinazine-ethyl);EL 77,亦即,5-氰基-1-(1,1-二甲基乙基)-N-甲基-1H-吡唑-4-甲醯胺;艾達殺(endothal);艾普丹(Iepoprodan);EPTC;艾普卡(esprocarb);艾殺淋(ethalfluralin);艾殺速龍(ethametsulfuron-ethyl);艾西隆(ethidimuron);艾西秦(ethiozin);艾梭特(ethofumesate);艾梭芬(ethoxyfen)及其酯類(例如,乙酯,HC-252);乙氧基舒福隆(ethoxysulfuron);依妥芬妮(etobenzanid)(HW 52);F5231,亦即,N-[2-氯基-4-氟基-5-[4-(3-氟基丙基)-4,5-二氫-5-酮基-1H-四唑-1-基]苯基]乙烷磺醯胺;芬諾普(fenoprop);芬諾山(fenoxan);芬殺草(fenoxaprop)以及芬殺草-P(fenoxaprop-P)及彼等之酯類,例如,芬殺草-P-乙基以及芬殺草-乙基;芬諾定(fenoxydim);芬特拉米(fentrazamide);芬有龍(fenuron);伏拉普(flamprop)(-甲基或-異丙機或-異丙基-L);伏速達(flazasulfuron);伏拉速爛(florasulam);伏寄普(fluazifop)以及伏寄普-P及彼等之酯類,例如,伏寄普-丁基(fluazifop-butyl)及伏寄普-P-丁基(fluazifop-P-butyl);伏若拉(fluazolate);伏咔唑(flucarbazone)(-鈉);伏克淋(fluchloralin);伏芬瑟(flufenacet)(FOE 5043);伏芬派(flufenpyr);伏速爛(flumetsulam);伏土隆(flumeturon);伏克剌(flumiclorac)(-戊基);伏山秦(flumioxazin)(S-482);伏普平(flumipropyn);伏滅隆(fluometuron);伏克動(flurochloridone);伏地芬(fluorodifen);伏利可芬(fluoroglycofen)(-乙基);伏珀擅(flupoxam)(KNW-739);伏普西(flupropacil)(UBIC-4243);伏帕西(flupropacil)(UBIC-4243);伏普納特(fluproanate);伏派舒福隆(flupyrsulfuron)(-甲基或-鈉);伏瑞諾(flurenol)(-甲基);伏立動(fluridone);氟氯比(fluroxypyr)(-甲基);伏皮密朵(flurprimidol);伏他蒙(flurtamone);伏賽瑟(fluthiacet)(-甲基);伏塞密(fluthiamide)(亦稱作為伏芬瑟(flufenacet));福草醚(fomesafen);福拉舒福隆(foramsulfuron);福殺明(fosamine);伏拉措(furilazole)(MON 13900);福西芬(furyloxyfen);固殺草(glufosinate)(-銨);嘉磷塞(glyphosate)(-異丙基-銨);哈殺芬(halosafen);哈速龍(halosulfuron)(-甲基)以及其酯類(例如,甲酯,NC-319);合氯氟(haloxyfop)以及其酯類;合氯氟-P(=R-合氯氟)及其酯類;HC-252;菲殺淨(hexazinone);依殺本(imazamethabenz)(-甲基);依殺必(imazamethapyr);依殺摩(imazamox);依殺皮(imazapic);依滅草(imazapyr);依馬奎(imazaquin)及其鹽類(諸如,銨鹽);依射必(imazethamethapyr);依射殺必(imazethapyr);依若舒福隆(imazofulfuron);印達汎(indanofan);碘基舒福隆(iodosulfuron)-(-甲基)-(鈉);碘苯腈(ioxynil);;咪草煙(imazethapyr);依速隆(imazosulfuron);異卡密(isocarbamid);異普淋(isopropalin);綠黃隆(isoproturon);愛速隆(isouron);異殺本(isoxaben);異立凡(isoxapyrifop);卡靈草(karbutilate);拉太芬(lactofen);聯納西(lenacil);理有龍(linuron);MCPA;MCPB;滅可普(mecoprop);滅芬草(mefenacet);滅伏地(mefluidid);美索舒福隆(-甲基);美索淬同(mesotrione);斯美地(metam);美他普(metamifop);苯草酮(metamitron);滅草胺(metazachlor);美賽龍(methabenzthiazuron);美殺蹤(methazole);甲氧基苯酮(methoxyphenone);甲基戴隆(methyldymron);美索本龍(methobenzuron);撲奪草(metobromuron);(S-)克草胺(metolachlor);美陀速攔(metosulam)(XRD 511);美陀隆(metoxuron);滅必淨(metribuzin);美速隆-甲基(metsulfuron-methyl);MK-616;稻得壯(molinate);莫納德(monalide);二氫硫酸單甲醯胺;莫淋隆(monolinuron);莫如隆(monuron);MT 128,亦即,6-氯基-N-(3-氯基-2-丙烯基)-5-甲基-N-苯基-3-嗒嗪胺;MT 5950,亦即,N-[3-氯基-4-(1-甲基乙基)苯基]-2-甲基戊醯胺;納安得(naproanilide);滅落脫(napropamide);納德爛(naptalam);NC 310,亦即,4-(2,4-二氯苯甲醯基)-1-甲基-5-苯氧基吡唑;內布隆(neburon);尼速隆(nicosulfuron);尼克芬(nipyraclophen);尼特淋(nitralin);護谷(nitrofen);尼伏芬(nitrofluorfen);諾伏蹤(norflurazon);奧本卡(orbencarb);奧札淋(oryzalin);奧迪幾(oxadiargyl)(RP-020630);樂滅草(oxadiazon);奧殺舒福隆(oxasulfuron);奧殺滅封(oxaziclomefone);復祿芬(oxyfluorfen);巴拉刈(paraquat);沛布拉(pebulate);壬酸;施得圃(pendimethalin);布舒爛(penoxulam);戊基拉草(pentanochlor);佈殺松(pentoxazone);佈福松(perfluidone);佈殺密(pethoxamid);菲異凡(phenisopham);菲地凡(phenmedipham);畢克攔(picloram);畢淋芬(picolinafen);派若凡(piperophos);畢布卡(piributicarb);畢芬諾-丁基(pirifenop-butyl);普拉草(pretilachlor);沛密黃隆-甲基(primisulfuron-methyl);普咔唑(procarbazone)(-鈉);普西淨(procyazine);普戴明(prodiamine);普伏挫(profluazole);四氯硝基苯(profluralin);普淋淨-乙基(proglinazine-ethyl);普滅陀(prometon);佈殺丹(prometryn);雷蒙得(propachlor);除草靈(propanil);普拔草(propaquizafop)以及其酯類;普帕淨(propazine);普凡(propham);普索克(propisochlor);丙氧基咔唑(propoxycarbazone)(-鈉);普查滅(propyzamide);普蘇淋(prosulfalin);普蘇卡(prosulfocarb);普速隆(prosulfuron)(CGA-152005);派那克(prynachlor);百克寧(pyraclonil);百伏芬(pyraflufen)(-乙基);百若淋(pyrazolinate);百拉蹤(pyrazon);百速隆-乙基(pyrazosulfuron-ethyl);百西芬(pyrazoxyfen);必本辛(pyribenzoxim);必佈卡(pyributicarb);必達伏(pyridafol);必汰草(pyridate);必他里(pyriftalid);密朵巴(pyrimidobac)(-甲基);必塞巴(pyrithiobac)(-鈉)(KIH-2031);必索伏(pyroxofop)以及其酯類(例如,炔丙酯);快克草(quinclorac);快美拉(quinmerac);快卡敏(quinoclamine);快諾伏(quinifop)及其酯類;快伏草(quizalofop)以及快伏草-P(quizalofop-P)及彼等之酯衍生物(例如,快伏草-乙基;快伏草-呋喃基以及-乙基);瑞杜隆(renriduron);淋黃隆(rimsulfuron)(DPX-E 9636);S 275,亦即,2-[4-氯基-2-氟基-5-(2-丙炔氧基)苯基]-4,5,6,7-四氫-2H-吲唑;色布陀(secbumeton);西殺草(sethoxydim);西杜隆(siduron);草滅淨(simazine);西滅翠(simetryn);SN 106279,亦即,2-[[7-[2-氯基-4-(三氟甲基)苯氧基]-2-萘基]氧基]丙酸以及其甲酯;蘇翠同(sulcotrione);蘇措蹤(sulfentrazon)(FMC-97285,F-6285);蘇入隆(sulfazuron);密黃隆(sulfometuron)(-甲基);硫復松(sulfosate)(ICI-A0224);磺酸基舒福隆(sulfosulfuron);TCA;特布譚(tebutam)(GCP-5544);得殺草(tepraloxydim);特巴西(terbacil);特布卡(terbucarb);特布克(terbuchlor);特滅陀(terbumeton);特布淨(terbuthylazine);特布翠(terbutryn);TFH 450,亦即,N,N-二乙基-3-[(2-乙基-6-甲基苯基)磺醯基]-1H-1,2,4-三唑-1-甲醯胺;仙克(thenylchlor)(NSK-850);賽伏米(thiafluamide);賽伏隆(thiazafluron);賽若比(thiazopyr)(Mon-13200);塞戴明(thidiazimin)(SN-24085);塞速隆(thifensulfuron)(-甲基);殺丹(thiobencarb);提巴幾(tiocarbazil);翠克西定(trialkoxydim);曲阿拉(tri-allate);曲速隆(triasulfuron);翠攔(triaziflam);曲芬明(triazofenamide);胺苯黃隆(tribenuron)(-甲基);2,3,6-三氯苯甲酸(2,3,6-TBA);三氯比(triclopyr);三地芬(tridiphane);三他淨(trietazine);三氟氧基舒福隆(trifloxysulfuron)(-鈉);三福林(trifluralin);三氟黃隆(triflusulfuron)以及其酯類(例如,甲酯,DPX-66037);三滅隆(trimeturon);翠陀舒福隆(tritosulfuron);其托得(tsitodef);畏挪拉(vernolate);WL 110547,亦即,5-苯氧基-1-[3-(三氟甲基)苯基]-1H-四唑;UBH-509;D-489;LS 82-556;KPP-300;NC-324;NC-330;KH-218;DPX-N8189;SC-0774;DOWCO-535;DK-8910;V-53482;PP-600;MBH-001;KIH-9201;ET-751;KIH-6127以及KIH-2023。
就有用植物及觀賞用植物之作物而言,選擇性地控制有害植物係特別具有重要性的。即使式(I)化合物對於許多作物,已呈現出非常佳至充分的選擇性,在理論上,在某些作物的耕種植物上還是可能發生植物毒性的症狀,且尤其在使用與其他選擇性較小之其他除草劑的混合物的情況下。就此方面而言,具重要性之依據本發明之式(I)化合物的倂合物為含有式(I)化合物或式(I)化合物與其他除草劑或殺蟲劑及保護劑之倂合物者。保護劑(彼等係以可使彼等呈現解毒作用的量來使用)可降低發生於,例如,具經濟價值之作物,諸如,穀類(大麥、小麥、裸麥、玉米、稻米、高梁以及粟)、甜菜、甘蔗、含油種子之油菜、棉花及大豆(宜為穀類)之所使用除草劑/殺蟲劑的植物毒性副作用。下文之化合物族群乃適用於式(I)化合物以及彼等與其他殺蟲劑之倂合物的保護劑例子;
a)二氯苯基吡唑啉-3-羧酸類型的化合物,較佳化合物為,諸如,1-(2,4-二氯苯基)-5-(乙氧羰基)-5-甲基-2-吡唑啉-3-羧酸乙酯(S1-1)(「美芬必-乙基(Mefenpyr-ethyl)」,PM,pp. 594-595)以及相關的化合物,如WO 91/07874所記載者;
b)二氯苯基吡唑羧酸衍生物,較佳化合物為,諸如,1-(2,4-二氯苯基)-5-甲基吡唑-3-羧酸乙酯(S1-2)、1-(2,4-二氯苯基)-5-異丙基吡唑-3-羧酸乙酯(S1-3)、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)吡唑-3-羧酸乙酯(S1-4)、1-(2,4-二氯苯基)-5-苯基吡唑-3-羧酸乙酯(S1-5)以及相關的化合物,如EP-A-333131以及EP-A-269 806所記載者;
c)三唑羧酸類型的化合物,較佳化合物為,諸如,芬克措(fenchlorazol)(以及其乙酯),亦即,1-(2,4-二氯苯基)-5-三氯甲基-(1H)-1,2,4-三唑-3-羧酸乙酯(S1-6),以及相關的化合物(參見EP-A-174 562以及EP-A-346 620);
d)5-苄基-或5-苯基-2-異噁唑啉-3-羧酸類型或5,5-二苯基-2-異噁唑啉-3-羧酸類型的化合物,較佳化合物為,諸如,5-(2,4-二氯苄基)-2-異噁唑啉-3-羧酸乙酯(S1-7)或5-苯基-2-異噁唑啉-3-羧酸乙酯(S1-8)以及相關的化合物(如WO 91/08202所記載者)、或5,5-二苯基-2-異噁唑啉羧酸乙酯(S1-9)[艾殺地芬-乙基(isoxadifen-ethyl)]或5,5-二苯基-2-異噁唑啉羧酸正丙酯(S1-10)或5-(4-氟苯基)-5-苯基-2-異噁唑啉-3-羧酸乙酯(S1-11)(如德國專利申請案(WO-A-95/07897)所記載者);
e)8-喹啉氧基乙酸類型(S2)的化合物,宜為(5-氯基-8-喹啉氧基)乙酸1-甲基己-1-基酯(俗名「克揆瑟-甲基(cloquinotcet-methyl)」(S2-1)(參見PM,pp. 195-196)(5-氯基-8-喹啉氧基)乙酸1,3-二甲基丁-1-基酯(S2-2),(5-氯基-8-喹啉氧基)乙酸4-烯丙基丁酯(S2-3),(5-氯基-8-喹啉氧基)乙酸1-烯丙基丙-2-基酯(S2-4),(5-氯基-8-喹啉氧基)乙酸乙酯(S2-5),(5-氯基-8-喹啉氧基)乙酸甲酯(S2-6),(5-氯基-8-喹啉氧基)乙酸烯丙酯(S2-7),(5-氯基-8-喹啉氧基)乙酸2-(2-亞丙基亞胺基氧基)-1-乙酯(S2-8),(5-氯基-8-喹啉氧基)乙酸2-酮基丙-1-基酯(S2-9),以及相關化合物,如EP-A-86 750、EP-A-94 349以及EP-A-191 736或EP-A-0 492 366所記載者;
f)(5-氯基-8-喹啉氧基)丙二酸類型的化合物,較佳的化合物為,諸如,(5-氯基-8-喹啉氧基)丙二酸二乙酯、(5-氯基-8-喹啉氧基)丙二酸二烯丙酯、(5-氯基-8-喹啉氧基)丙二酸甲酯乙酯以及相關的化合物,如EP-A-0 582 198所記載者;
g)苯氧基乙酸或苯氧基丙酸衍生物類型或芳族羧酸類型的活性物質,諸如,例如,2,4-二氯苯氧基乙酸類(及彼等之酯類)(2,4-D),4-氯基-2-甲基苯氧基丙酸酯類[滅可普(mecoprop)],MCPA或3,6-二氯基-2-甲氧基苯甲酸(及其酯類)[麥草畏(dicamba)];
h)嘧啶類型的活性化合物,彼等係用於稻米,作為作用於土壤的保護劑,諸如,例如,「芬克淋(fenclorim)」(PM,pp. 386-387)(=4,6-二氯基-2-苯基嘧啶),其亦已知可用於稻苗,作為對於普拉草(pretilachlor)的保護劑;
i)二氯乙醯胺類型的活性物質,彼等常用作為萌前保護劑(作用於土壤的保護劑),諸如,例如,「代剋密(dichlormid)」(PM,pp. 270-271)(=N,N-二烯丙基-2,2-二氯乙醯胺),「R-29148」(=3-二氯乙醯基-2,2,5-三甲基-1,3-噁唑啶,Stauffer的產品),「本殺可(benoxacor)」(PM,pp. 74-74)(=4-二氯乙醯基-3,4-二氫-3-甲基-2H-1,4-苯並噁嗪),「PPG-1292」(=N-烯丙基-N-[(1,3-二氧戊環-2-基)甲基]二氯乙醯胺,PPG Industries的產品),「DK-24」(=N-烯丙基-N-[(烯丙基胺基羰基)甲基]二氯乙醯胺,Sagro-Chem的產品),「AD-67」或「MON 4660」(=3-二氯乙醯基-1-氧雜-3-氮雜螺[4,5]癸烷,分別為Nitrokemia及Monsanto的產品),「代剋農(diclonon)」或「BAS 145138」或「LAB145138」(=3-二氯乙醯基-2,5,5-三甲基-1,3-二氮雜二環[4.3.0]壬烷,BASF的產品)以及「伏拉措(furilazol)」或「MON 13900」(參見PM,482-483)(=(RS)-3-二氯乙醯基-5-(2-呋喃基)-2,2-二甲基噁唑啉);
j)二氯丙酮類型的活性物質,諸如,例如,「MG 191」(CAS登記編號96420-72-3)(=2-二氯甲基-2-甲基-1,3-二氧戊環,Nitrokemia的產品),其乃已知可作為玉米的保護劑;
k)氧基亞胺基化合物類型的活性物質,彼等已知為種子處理產物,諸如,例如,「奧殺翠尼(oxabetrinil)」(PM,pp. 689)(=(Z)-1,3-二氧戊環-2-基甲氧基亞胺基(苯基)乙腈),其已知為高梁及粟的種子處理保護劑,用以對抗克草胺(metolachlor)損害,「伏索芬寧(fluxofenim)」(PM,pp. 467-468)(=1-(4-氯苯基)-2,2,2-三氟基-1-乙酮O-(1,3-二氧戊環-2-基甲基)肟,其已知為高梁及粟的浸種保護劑,用以對抗克草胺(metolachlor)損害,以及「塞美翠尼(cyometrinil)」或「CGA-43089」(PM,p. 1170)(=(Z)-氰基甲氧基亞胺基(苯基)乙腈),其已知為高梁及粟之種子處理保護劑,用以對抗克草胺(metolachlor)損害;
l)噻唑羧酸酯類型的活性物質,彼等已知為種子處理產品,諸如,例如,「伏拉措(flurazole)」(PM,pp. 450-451)(=2-氯基-4-三氟甲基-1,3-噻唑-5-羧酸苄酯),其已知為高梁及粟的種子處理保護劑,用以對抗拉草(alachlor)及克草胺(metolachlor)損害;
m)萘二羧酸衍生物類型的活性物質,彼等已知為種子處理產品,諸如,例如,「萘酸酐」(PM,p. 1009-1010)(=1,8-萘二羧酸酐),其已知為玉米之種子處理保護劑,用以對抗硫代胺甲酸酯類除草劑的損害;
n)色滿乙酸衍生物類型的活性物質,諸如,例如,「CL 304415」(CAS登記號31541-57-8)(=2-(4-羧基色滿-4-基)乙酸,American Cyanamid的產品),其已知為保護玉米以對抗咪唑啉酮類之損害的保護劑;
o)除了對抗有害植物之除草作用之外,亦呈現出對於作物植物(諸如,稻米)之保護劑作用的活性物質,諸如,例如,「代美沛拉(dimepiperate)」或「MY-93」(PM,pp. 302-303)(=六氫吡啶-1-硫代羧酸S-1-甲基-1-苯基乙酯),其已知為保護稻米以對抗除草劑稻得壯(molinate)之損害的保護劑;「戴木隆(daimuron)」或「SK 23」(PM,p. 247)(=1-甲基-1-苯乙基)-3-甲苯基脲),其已知為保護稻米以對抗除草劑依速隆(imazosulfuron)之損害的保護劑,「庫陸隆(cumyluron)」=「JC-940」(=3-(2-氯苯基甲基)-1-(1-甲基-1-苯乙基)脲,參見JP-A-60087254),其已知為保護稻米對抗多種除草劑之損害的保護劑,「甲氧基苯基酮」或「NK 049」(=3,3'-二甲基-4-甲氧基苯並苯基酮),其已知為保護稻米以對抗多種除草劑之損害的保護劑,「CSB」(=1-溴基-4-(氯甲基磺醯基)苯)(CAS登記號54091-06-4,Kumiai的產品),其已知為保護稻米對抗多種除草劑之損害的保護劑,
p)式(S3)所示之N-醯基磺醯胺類及彼等之鹽類,如WO-A-97/45016所記載者
q)式(S4)所示之醯基胺磺醯基苯甲醯胺,視需要,亦包括彼等之鹽形式,如國際專利申請案PCT/EP98/06097所記載者;
以及
r)式(S5)所示之化合物,如WO-A-98/13 361所記載者,
包括立體異構物以及農業上習用的鹽類。
在前述保護劑中,特別重要的為(S1-1)及(S1-9)與(S2-1),尤其是(S1-1)及(S1-9)。某些保護劑已知可作為除草劑,因此除了對於有害植物有除草作用之外,同時對於作物植物亦呈現出保護作用。
除草劑(混合物)相對於保護劑的重量比通常係取決於除草劑的噴佈量以及所用之保護劑的功效,該比例可在寬廣的限制內變動,例如,在200:1至1:200的範圍內,宜為100:1至1:100,尤指20:1至1:20。彼等保護劑可與其他的除草劑/殺蟲劑調配在一起,與式(I)化合物或彼等之混合物類似地,且與除草劑一起以預混合物或槽混合物的形式提供及使用。
使用時,以習用之市販形式存在之除草劑或除草劑/保護劑製劑,視需要,係以習用的方式進行稀釋,例如,使用水(在可潤濕的散劑、可乳化的濃體、分散劑及水可分散粒劑的情況下)。呈散劑、土壤用粒劑、噴灑粒劑以及可噴灑的溶液在使用前,通常係不用其他的惰性物質進一步稀釋的。
所需要之式(I)化合物的噴佈量係隨著,尤其是,外部條件,諸如,溫度、溼度及所採用之除草劑的類型而改變的。該噴佈量可在寬廣的限制內變化,例如,0.001至10.0 kg(活性物質)/ha之間或更多,但是宜在0.002至3 kg/ha之間,尤指在0.005至1 kg/ha之間。
B.製劑實施例
a)粉劑可藉由下列方法製得:將10重量份之式(I)化合物及90重量份之滑石(作為惰性物質)混合在一起並於錘磨機內,將所得到的混合物磨碎。
b)易於分散於水的可潤濕粉劑係藉由下列方法得到的:將25重量份之式(I)化合物、64重量份之含高嶺土的石英(作為惰性物質)、10重量份木質素磺酸鉀以及1重量份之油醯基甲基牛膽素鈉(作為潤濕劑及分散劑)並於閉合式圓盤磨碎機內研磨該混合物。
c)易分散於水中之分散濃體係藉由下列方式得到的:將20重量份之式(I)化合物、6重量份之烷基酚多二醇醚(X 207)、3重量份之異十三烷醇多二醇醚(8EO)以及71重量份之石蠟系礦油(沸點範圍為,例如,約255至277℃以上),並於球磨機內,將該混合物研磨至粒度小於5μ。
d)可乳化的濃體可由15重量份式(I)化合物、75重量份環己酮(作為溶劑)以及10重量份氧乙基化壬基酚(作為乳化劑)得到。
e)水可分散的粒劑係藉由將下列方式得到:將下列成分混合在一起
75重量份 式(I)化合物
10重量份 木質素磺酸鈣
5重量份 月桂基硫酸鈉
3重量份 聚乙烯基醇以及
7重量份 高嶺土,
在閉合式圓盤磨碎機內,研磨該混合物,並於流化床內,將所得到的粉末噴灑於水(作為粒化液)上,而予以粒化。
f)另外,水可分散的粒劑亦可藉由下列方式得到:於膠體磨碎機內,將下列成分均化及預研磨,
25重量份 式(I)化合物
5重量份 2,2'-二萘基甲烷-6,6'-二磺酸鈉
2重量份 油醯基甲基牛膽素鈉
1重量份 聚乙烯醇
17重量份 碳酸鈉以及
50重量份 水
接著,在珠粒磨碎機內,研磨該混合物,並於噴淋塔中,藉助單一物質噴嘴(single-substance nozzle),將所得到的懸浮液霧化以及乾燥。
C.生物實施例
生物實施例1:對於雜草的萌前效果
將單子葉以及雙子葉雜草植物的種子或地下莖的片段置於塑膠缽的砂壤土中,蓋上土壤。以各種不同的劑量,將本發明之化合物(其係調配為可潤濕的散劑或乳化濃體的形式),以水懸浮液或乳液的形式,噴灑至土壤表面,噴佈量為600至800 L(水)/ha(已經過轉化)。
在處理過後,將塑膠缽置於溫室中並將彼等保持在良好的生長條件下數星期。在3至4星期後,於受試植物已發芽後,藉由與未經處理的對照組的比較之下,以肉眼來評估植物或出苗的損害。
當以每公畝施用1kg或更少之活性成分的噴佈量來施用時,本發明之化合物編號1.1、1.2、1.3、1.7、1.11、1.12、1.15、1.20、1.21、1.24、1.28、1.31、1.66、1.67、1.68、1.69、2.1、2.2、2.4、2.11、2.25、2.28、3.1、3.2、3.7、3.11、3.15、3.20、3.24、4.1、4.2、5.1、5.2、6.1、6.2、7.1、7.2、7.3、7.4、7.11、7.24、7.47、7.48、7.57、7.70、7.72、7.74、7.75、7.78、7.203、7.228、7.229、7.238、7.239、7.240、7.241、7.242、7.243、7.244、7.245、8.1、8.2、8.3、8.7、8.11、8.12、8.15、8.21、8.24、8.25、8.26、8.34、8.35、8.38、8.44、8.48、8.49、8.58、8.61、8.67、8.68、8.71、8.75、8.79、8.90、8.100、8.113、8.117、8.148、8.152、8.160、8.170、8.183、8.187、8.195、8.196、8.197、8.201、8.205、8.206、8.209、8.215、8.219、8.231、8.233、8.234、8.237、8.238、8.239、8.240、8.241、8.242、8.243、8.244、8.245、8.246、8.247、8.248、8.249、8.250、8.251、8.252、8.253、8.254、8.255、8.256、8.257、9.36、9.37、9.66、10.1、10.2、10.37、10.38、10.47、10.57、10.66、10.67以及10.68對於有害植物,諸如,小花繁縷(Stellaria media)、多花黑麥草(Lolium multiforum)、野莧(Amaranthus reftroflexus)、白芥子(Sinapis alba)、野燕麥(Avena sativa)及青狗尾草(Setaria viridis),呈現出非常佳的萌前控制。
將單子葉以及雙子葉有害植物的種子或地下莖的片段置於塑膠缽的砂壤土中,蓋上土壤,並於溫室中,在良好的生長條件下生長。在播種2至3星期後,於三葉階段,對受試植物進行處理。以各種不同的劑量,將本發明之化合物(其係調配為可潤濕的散劑或乳化濃體的形式),噴灑至植物的綠色部分,噴佈量為600至800 L(水)/ha(已經過轉化)。在受試植物於最佳生長條件下之溫室中待了3至4星期後,藉由與未處理的對照組比較,以肉眼來評估製劑的效果。當以每公畝施用2 kg或更少之活性成分的噴佈量來施用時,本發明之化合物編號1.1、1.2、1.3、1.7、1.11、1.12、1.15、1.20、1.21、1.24、1.28、1.31、1.66、1.67、1.68、1.69、2.1、2.2、2.4、2.11、2.25、2.28、3.1、3.2、3.7、3.11、3.15、3.20、3.24、4.1、4.2、5.1、5.2、6.1、6.2、7.1、7.2、7.3、7.4、7.11、7.24、7.47、7.48、7.57、7.70、7.72、7.74、7.75、7.78、7.203、7.228、7.229、7.238、7.239、7.240、7.241、7.242、7.243、7.244、7.245、8.1、8.2、8.3、8.7、8.11、8.12、8.15、8.21、8.24、8.25、8.26、8.34、8.35、8.38、8.44、8.48、8.49、8.58、8.61、8.67、8.68、8.71、8.75、8.79、8.90、8.100、8.113、8.117、8.148、8.152、8.160、8.170、8.183、8.187、8.195、8.196、8.197、8.201、8.205、8.206、8.209、8.215、8.219、8.231、8.233、8.234、8.237、8.238、8.239、8.240、8.241、8.242、8.243、8.244、8.245、8.246、8.247、8.248、8.249、8.250、8.251、8.252、8.253、8.254、8.255、8.256、8.257、9.36、9.37、9.66、10.1、10.2、10.37、10.38、10.47、10.57、10.66、10.67以及10.68對於有害植物,諸如,白芥子(Sinapis alba)、台灣野稗(Echinochloa crus-galli)、多花黑麥草(Lolium multiflorum)、小花繁縷(Stellaria media)、碎米莎草(Cyperus iria)、野莧(Amaranthus retroflexus)、青狗尾草(Setaria viridis)、野燕麥(Avena sativa)、Lamium purpureum、無香味母菊(Matricaria inodora)、虞美人(Papaver rhoeas)、大婆婆納(Veronica persica)、堇菜(Viola trocolor)、地膚(Kochia spp)以及小葉藜(Chenopodium album),呈現出非常佳的萌後除草活性。
在另外的田地試驗中,於長滿天然雜草的條件下,讓種植作物生長並噴灑各種不同劑量之依據本發明的式(I)化合物。在噴佈後,於各種不同的間隔,藉由視覺評估,可發現到依據本發明之化合物即使在高活性物質噴佈量下,並不會損害種植作物,諸如,例如,油椰、椰子樹、印度橡樹、柑桔類、鳳梨、仁果、棉花、咖啡、可可及葡萄。與先前技藝相較之下,式(I)化合物呈現出改良程度的選擇性,因此適用於控制種植作物中之不想要的草木。此外,當將本發明之化合物於雜草的萌前階段施用時,對於雜草的控制特別地極佳。
Claims (2)
- 一種式(Va)所示之化合物或其鹽類,
- 一種式(XIII)所示之化合物或其鹽類,
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP03002438 | 2003-02-05 | ||
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TW093102423A TWI357411B (en) | 2003-02-05 | 2004-02-03 | Amino-1,3,5-triazines n-substituted with chiral bi |
TW100101093A TWI391094B (zh) | 2003-02-05 | 2004-02-03 | N-經對掌性二環基團取代之胺基-1,3,5-三嗪化合物,其製法,組成物及其用作除草劑和植物生長調節劑之用途 |
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US (2) | US8114991B2 (zh) |
EP (2) | EP1592674B1 (zh) |
JP (2) | JP4753258B2 (zh) |
KR (2) | KR101224300B1 (zh) |
CN (1) | CN100448850C (zh) |
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Families Citing this family (49)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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TW200837064A (en) | 2006-10-04 | 2008-09-16 | Pharmacopeia Inc | 8-substituted 2-(benzimidazolyl)purine derivatives for immunosuppression |
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JP2023521343A (ja) | 2020-04-09 | 2023-05-24 | バイエル・アクチエンゲゼルシヤフト | 優れた除草活性を有する化合物組合せ |
IL297163A (en) | 2020-04-09 | 2022-12-01 | Bayer Ag | Combination of compounds with excellent herbicidal activity |
WO2022165402A1 (en) | 2021-02-01 | 2022-08-04 | Blueprint Medicines Corporation | Inhibitors of protein kinase a |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996021640A1 (en) * | 1995-01-12 | 1996-07-18 | Teva Pharmaceutical Industries, Ltd. | Optically active aminoindane derivatives and preparation thereof |
EP0864567A1 (en) * | 1995-11-27 | 1998-09-16 | Idemitsu Kosan Company Limited | Triazine derivatives |
WO1998047877A1 (en) * | 1997-04-22 | 1998-10-29 | Glaxo Group Limited | 2-benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide derivatives and their use as inhibitors of hepatic production of apob-100 |
US6069114A (en) * | 1996-02-28 | 2000-05-30 | Hoechst Schering Agrevo Gmbh | 2-amino-4-bicycloamino-1,3,5-Triazines, their preparation, and their use as herbicide and plant growth regulators |
JP2002065286A (ja) * | 2000-08-29 | 2002-03-05 | Nippon Steel Chem Co Ltd | 光学活性(r)‐1‐インダンアミド誘導体およびその製造方法 |
Family Cites Families (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3637740A (en) * | 1969-04-21 | 1972-01-25 | Pfizer | Aminobenzocycloalkane compounds |
US4096173A (en) * | 1977-03-28 | 1978-06-20 | Eli Lilly And Company | Chlorinated 1-aminoindane N-methyl transferase inhibitors |
US4132737A (en) * | 1978-02-27 | 1979-01-02 | Eli Lilly And Company | Trifluoromethyl substituted 1-aminoindanes |
MA19709A1 (fr) | 1982-02-17 | 1983-10-01 | Ciba Geigy Ag | Application de derives de quinoleine a la protection des plantes cultivees . |
EP0094349B1 (de) | 1982-05-07 | 1994-04-06 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
EP0131624B1 (en) | 1983-01-17 | 1992-09-16 | Monsanto Company | Plasmids for transforming plant cells |
BR8404834A (pt) | 1983-09-26 | 1985-08-13 | Agrigenetics Res Ass | Metodo para modificar geneticamente uma celula vegetal |
JPS6087254A (ja) | 1983-10-19 | 1985-05-16 | Japan Carlit Co Ltd:The | 新規尿素化合物及びそれを含有する除草剤 |
DE3525205A1 (de) | 1984-09-11 | 1986-03-20 | Hoechst Ag, 6230 Frankfurt | Pflanzenschuetzende mittel auf basis von 1,2,4-triazolderivaten sowie neue derivate des 1,2,4-triazols |
BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
EP0191736B1 (de) | 1985-02-14 | 1991-07-17 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
US4631211A (en) | 1985-03-25 | 1986-12-23 | Scripps Clinic & Research Foundation | Means for sequential solid phase organic synthesis and methods using the same |
ATE80182T1 (de) | 1985-10-25 | 1992-09-15 | Monsanto Co | Pflanzenvektoren. |
EP0242236B2 (en) | 1986-03-11 | 1996-08-21 | Plant Genetic Systems N.V. | Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering |
IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
DE3633840A1 (de) | 1986-10-04 | 1988-04-14 | Hoechst Ag | Phenylpyrazolcarbonsaeurederivate, ihre herstellung und verwendung als pflanzenwachstumsregulatoren und safener |
DE3808896A1 (de) | 1988-03-17 | 1989-09-28 | Hoechst Ag | Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten |
DE3817192A1 (de) | 1988-05-20 | 1989-11-30 | Hoechst Ag | 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols |
US4948395A (en) * | 1989-09-12 | 1990-08-14 | Advanced Separations Technologies Inc. | Chiral separation media |
DE3939010A1 (de) | 1989-11-25 | 1991-05-29 | Hoechst Ag | Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschuetzende mittel |
DE3939503A1 (de) | 1989-11-30 | 1991-06-06 | Hoechst Ag | Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden |
ATE241007T1 (de) | 1990-03-16 | 2003-06-15 | Calgene Llc | Dnas, die für pflanzliche desaturasen kodieren und deren anwendungen |
EP0536293B1 (en) | 1990-06-18 | 2002-01-30 | Monsanto Technology LLC | Increased starch content in plants |
DK0536330T3 (da) | 1990-06-25 | 2002-04-22 | Monsanto Technology Llc | Glyphosattolerante planter |
DE59108636D1 (de) | 1990-12-21 | 1997-04-30 | Hoechst Schering Agrevo Gmbh | Neue 5-Chlorchinolin-8-oxyalkancarbonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antidots von Herbiziden |
SE467358B (sv) | 1990-12-21 | 1992-07-06 | Amylogene Hb | Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp |
DE4104782B4 (de) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide |
TW259690B (zh) | 1992-08-01 | 1995-10-11 | Hoechst Ag | |
DE4331448A1 (de) | 1993-09-16 | 1995-03-23 | Hoechst Schering Agrevo Gmbh | Substituierte Isoxazoline, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener |
US5914349A (en) * | 1994-01-10 | 1999-06-22 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
DE69535315T2 (de) * | 1994-01-10 | 2007-06-28 | Teva Pharmaceutical Industries Ltd. | 1-aminoindanderivate und zusammensetzungen hiervon |
JPH08183781A (ja) * | 1994-12-28 | 1996-07-16 | Idemitsu Kosan Co Ltd | トリアジン誘導体およびそれを有効成分とする除草剤 |
DE19604191A1 (de) | 1996-02-06 | 1997-08-07 | Hoechst Schering Agrevo Gmbh | 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE19614718A1 (de) * | 1996-04-15 | 1997-10-16 | Hoechst Schering Agrevo Gmbh | Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung, und ihre Verwendung als Schädlingsbekämpfungsmittel |
DE19621522A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Schering Agrevo Gmbh | Neue N-Acylsulfonamide, neue Mischungen aus Herbiziden und Antidots und deren Verwendung |
EP0929543B1 (en) | 1996-09-26 | 2001-10-31 | Syngenta Participations AG | Herbicidal composition |
DE10207037A1 (de) * | 2002-02-20 | 2003-08-28 | Bayer Cropscience Gmbh | 2-Amino-4-bicyclyamino-6H-1,3.5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
WO2003099266A2 (en) * | 2002-05-23 | 2003-12-04 | Abbott Laboratories | Acetamides and benzamides that are useful in treating sexual dysfunction |
-
2004
- 2004-01-23 EA EA200501161A patent/EA012406B1/ru not_active IP Right Cessation
- 2004-01-23 AP AP2005003386A patent/AP1960A/xx active
- 2004-01-23 PL PL378410A patent/PL222483B1/pl unknown
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- 2004-01-23 EP EP04704591.9A patent/EP1592674B1/en not_active Expired - Lifetime
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- 2004-01-23 KR KR1020057014463A patent/KR101213248B1/ko active IP Right Grant
- 2004-01-23 EP EP10185534A patent/EP2305655A3/en not_active Withdrawn
- 2004-01-23 DK DK04704591.9T patent/DK1592674T3/da active
- 2004-01-23 JP JP2006501582A patent/JP4753258B2/ja not_active Expired - Lifetime
- 2004-01-23 PT PT47045919T patent/PT1592674E/pt unknown
- 2004-02-03 AR ARP040100332A patent/AR043014A1/es not_active Application Discontinuation
- 2004-02-03 US US10/771,649 patent/US8114991B2/en not_active Expired - Lifetime
- 2004-02-03 TW TW093102423A patent/TWI357411B/zh not_active IP Right Cessation
- 2004-02-03 TW TW100101093A patent/TWI391094B/zh not_active IP Right Cessation
- 2004-02-05 MY MYPI20040350A patent/MY140171A/en unknown
-
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- 2005-07-13 ZA ZA200505626A patent/ZA200505626B/xx unknown
- 2005-07-22 CR CR7920A patent/CR7920A/es unknown
- 2005-07-25 IL IL169877A patent/IL169877A/en active IP Right Grant
- 2005-07-27 EC EC2005005934A patent/ECSP055934A/es unknown
- 2005-08-03 CO CO05076616A patent/CO5590957A2/es not_active Application Discontinuation
- 2005-08-04 HR HRP20050702AA patent/HRP20050702B1/hr not_active IP Right Cessation
-
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- 2010-09-30 JP JP2010220690A patent/JP2011037870A/ja active Pending
-
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- 2011-04-21 AU AU2011201831A patent/AU2011201831B2/en not_active Expired
- 2011-12-28 US US13/338,351 patent/US20120101287A1/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996021640A1 (en) * | 1995-01-12 | 1996-07-18 | Teva Pharmaceutical Industries, Ltd. | Optically active aminoindane derivatives and preparation thereof |
EP0864567A1 (en) * | 1995-11-27 | 1998-09-16 | Idemitsu Kosan Company Limited | Triazine derivatives |
US6069114A (en) * | 1996-02-28 | 2000-05-30 | Hoechst Schering Agrevo Gmbh | 2-amino-4-bicycloamino-1,3,5-Triazines, their preparation, and their use as herbicide and plant growth regulators |
WO1998047877A1 (en) * | 1997-04-22 | 1998-10-29 | Glaxo Group Limited | 2-benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide derivatives and their use as inhibitors of hepatic production of apob-100 |
JP2002065286A (ja) * | 2000-08-29 | 2002-03-05 | Nippon Steel Chem Co Ltd | 光学活性(r)‐1‐インダンアミド誘導体およびその製造方法 |
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