CN1194638A - 取代的氰基苯基尿嘧啶 - Google Patents
取代的氰基苯基尿嘧啶 Download PDFInfo
- Publication number
- CN1194638A CN1194638A CN96196652A CN96196652A CN1194638A CN 1194638 A CN1194638 A CN 1194638A CN 96196652 A CN96196652 A CN 96196652A CN 96196652 A CN96196652 A CN 96196652A CN 1194638 A CN1194638 A CN 1194638A
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- CN
- China
- Prior art keywords
- group
- methyl
- fluoro
- alkyl
- phenyl
- Prior art date
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- 125000004802 cyanophenyl group Chemical group 0.000 title claims description 18
- 238000000034 method Methods 0.000 claims abstract description 33
- -1 cyano- Chemical class 0.000 claims description 301
- 150000001875 compounds Chemical class 0.000 claims description 94
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 239000011737 fluorine Substances 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 241000238631 Hexapoda Species 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000001345 alkine derivatives Chemical class 0.000 claims description 10
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003566 oxetanyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052728 basic metal Inorganic materials 0.000 claims description 4
- 150000003818 basic metals Chemical class 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- JDYGHOOLHQSNTK-UHFFFAOYSA-N 4-(1,3-thiazol-2-yl)oxadiazole Chemical compound C1=CSC(C=2N=NOC=2)=N1 JDYGHOOLHQSNTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000005981 pentynyl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000002053 thietanyl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 10
- JGWWBSUUFGBHCH-UHFFFAOYSA-N 2-phenylpyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC(C=2C=CC=CC=2)=N1 JGWWBSUUFGBHCH-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 39
- 239000002917 insecticide Substances 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000003795 chemical substances by application Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000003995 emulsifying agent Substances 0.000 description 13
- 239000003999 initiator Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000003851 azoles Chemical class 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 238000009835 boiling Methods 0.000 description 7
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
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- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
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Abstract
本发明涉及通式(Ⅰ)新的取代的氰基苯基尿嘧啶,其中R1、R2、R3、R4、R5和Q各自在说明书中定义,它们的制备方法,涉及新的中间体,并涉及它们作为除草剂和杀虫剂的用途。
Description
本发明涉及一种新的取代的氰基苯基尿嘧啶,其制备方法,以及其作为农作物处理剂,特别是作为除草剂和杀虫剂的用途。
已知一些取代的苯基尿嘧啶具有除草剂性质(参见EP-408 382/US-5 084 084/US-5 127 935/US-5 154 755,EP-563 384,EP-648 749,WO 91/00278,US-4 979 982,US-5 169 430)。但是到目前为止,这些化合物还没有获得任何重要性。
本发明提供通式(I)新的取代的氰基苯基尿嘧啶:
其中:Q代表O、S、SO或SO2,R1代表氢、氰或卤原子,R2代表氢,或者代表选自下组的各自可有可无地被取代的残基:烷基、链烯基、炔烃基、环烷基、环烷基烷基、芳基、芳基烷基、杂环基和杂环基烷基,R3代表氢、卤原子或者代表选自下组的各自可有可无地被取代的残基:烷基和烷氧基,R4代表可有可无地被取代的烷基,和R5代表氢,或者代表选自下组的各自可有可无地被取代的残基:烷基、烷氧基、链烯基和炔烃基,但是排除已知的化合物1-(4-氰基-2-氟-5-甲基硫基-苯基)-3,6-二氢-2,6-二氧-3-甲基-4-三氟甲基-1(2H)-嘧啶,1-(4-氰基-2-氟-5-甲氧基羰基甲基硫-苯基)-3,6-二氢-2,6-二氧-3-甲基-4-三氟甲基-1(2H)-嘧啶和1-〔4-氰基-2-氟-5-(1-乙氧基羰基-乙基硫)-苯基〕-3,6-二氢-2,6-二氧-3-甲基-4-三氟甲基-1(2H)-嘧啶(参见EP-408382,p.85和U.S.-5084084,Col.76)。
当发生下面反应时得到通式(I)新的取代的氰基苯基尿嘧啶。(a)如果适当,存在一种反应助剂,和如果适当,存在一种稀释剂,通式(II)取代的卤代苯基尿嘧啶其中:R1、R3、R4和R5各自如上定义,和X代表卤原子,与通式(III)亲核化合物反应
M-Q-R2 (III)其中Q和R2各自如上定义,和M代表氢或碱金属,或者(b)如果适当,存在一种反应助剂和如果适当,存在一种稀释剂,通式(Ia)取代的氰基苯基尿嘧啶其中Q、R1、R2、R3和R4各自如上定义,与一种烷基化试剂反应。
通式(I)新的取代的氰基苯基尿嘧啶具有强的除草活性和杀虫活性。
在这些定义中,饱和或不饱和的烃链,例如烷基、链烯基或炔烃基,在各种情况下是直链或支链的。
卤原子一般代表氟、氯、溴或碘,优选氟、氯、溴,特别是氟或氯。
本发明优选提供式(I)化合物。其中Q代表O、S、SO或SO2,R1代表氢、氰基、氟或氯,R2代表氢,代表分别可有可无地被氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷氧基-、C1-C4-烷基-羰基-、C1-C4-烷氧基-羰基-、二(C1-C4-烷基)-氨基-羰基-或N-C1-C4-烷基-N-苯基-氨基-羰基-(其中苯基可有可无地被氟、氯、溴、氰基、硝基、甲基或甲氧基取代)取代的、各种情况下至多有10个碳原子的烷基、链烯或炔烃基,代表分别可有可无地被氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基取代的、在环烷基部分有3-8个碳原子且可有可无地在烷基部分最多有4个碳原子的环烷基或环烷基烷基,代表分别可有可无地被氰基-、羧基-、硝基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-,或C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基硫基-、C1-C4-烷基亚磺酰基-、C1-C4-烷基磺酰基-、C1-C4-烷基羰基-或C1-C4-烷氧基-羰基-(各自可有可无地被氟和/或氯取代),或苯基-、苯氧基-或苯基硫-(各自可有可无地被氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代的、在芳基部分有6或10个碳原子和可有可无地在烷基部分至多有4个碳原子的芳基或芳基烷基,R2进一步代表各自可有可无地被氰基-、羧基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-或C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基硫基-、C1-C4-烷基亚磺酰基-、C1-C4-烷基磺酰基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基-(各基团可有可无地被氟和/或氯取代),或苯基-、苯氧基-或苯基硫基-(各基团可有可无地被氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代的取代呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、氧杂环丁烷基(oxetanyl)、thietanyl、噁唑基、异噁唑基、噻唑基、噁二唑基、噻二唑基、吡唑基、吡啶基、嘧啶基、三嗪基、吲哚基、喹啉基或喹喔啉基,R3代表氢、氟、氯、溴或代表各自可有可无地被氟-和/或氯取代的、每种情况下有1至4个碳原子的烷基或烷氧基,R4代表可有可无地被氟和/或氯-取代的、有1-4个碳原子的烷基,和R5代表氢或代表各自可有可无地被氟-、氯-或C1-C4-烷氧基取代的、各种情况下最多有6个碳原子的烷基、烷氧基、链烯基或炔烃基,但是排除已知化合物1-(4-氰基-2-氟-5-甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1-(4-氰基-2-氟-5-甲氧基羰基甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和1-〔4-氰基-2-氟-5-(1-乙氧基羰基-乙基硫)-苯基〕-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶(参见EP-408 382,p.85和US-5 084 084,Col.76)。
本发明特别提供式(I)化合物,其中Q代表O、S、SO或SO2,R1代表氢、氟或氯,R2代表氢,代表各自可有可无地被氰基-、羧基-、氟-、氯-、甲氧基-、乙氧基-、正-或异-丙氧基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或异-丙氧基羰基-、二甲基氨基羰基-或二乙基氨基羰基-取代的甲基、乙基、正-或异-丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、丙烯基、丁烯基、戊烯基、丙炔基、丁炔基或戊炔基,R2进一步代表各自可有可无地被氰基-、羧基-、氟-、氯-、溴-、甲基-、乙基-、正-或异-丙基-、甲氧基-、乙氧基-、正-或异-丙氧基-、乙酰基-或丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或异-丙氧基羰基-取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,R2进一步代表各自可有可无地被氰基-、羧基-、硝基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正-或异-丙基-、正-、异-、仲-或叔丁基-、三氟甲基-、甲氧基-、乙氧基-、正-或异-丙氧基-、甲基硫基-、乙基硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或异-丙氧基羰基-取代的苯基、苄基或苯基乙基,或R2进一步代表各自可有可无地被氰基-、羧基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正-或异-丙基-、甲氧基-、乙氧基-、正-或异-丙氧基-、甲基硫基-、乙基硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或异-丙氧基羰基-或苯基-、苯氧基-或苯基硫基-取代的呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、氧杂环丁烷基(oxetanyl)、thietanyl、噁唑基、异噁唑基、噻唑基、噁二唑基、噻二唑基、吡唑基、吡啶基、嘧啶基、三嗪基、吲哚基、喹啉基或喹喔啉基,R3代表氢、氟、氯、溴或甲基,R4代表甲基、乙基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯代二氟甲基、氟代二氯甲基、氯乙基、氟乙基、二氯乙基、氯代氟代乙基、氯代二氟乙基、氟代二氯乙基、三氟乙基、四氟乙基、氯代三氟乙基或五氟乙基和R5代表氢或代表各自可有可无地被氟-、氯-、甲氧基-或乙氧基-取代的甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-或仲丁氧基、丙烯基、丁烯基、丙炔基或丁炔基,但是排除已知化合物1-(4-氰基-2-氟-5-甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1-(4-氰基-2-氟-5-甲氧基羰基甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和1-〔4-氰基-2-氟-5-(1-乙氧基羰基-乙基硫基)-苯基〕-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶(参见EP-408 382,p.85和US-5 084 084,Col.76)。
上文概括或优选残基定义适用于式(I)终产物,而且以相对应方式也适用于在各种情况下制备时所需要的起始物或中间体。这些残基定义可以随意相互结合,即也可能在给定的优选范围之间结合。
本发明式(I)化合物的实施例在下面的组中列出。第1组R2 例如具有下面列出的定义:氢、甲基、乙基、正-或异-丙基、正-、异-、仲-或叔丁基、正异-、仲-或叔戊基、二氟甲基、三氟甲基。、氯代二氟甲基、氟代二氯甲基、氟乙基、氯乙基、氯代氟代乙基、二氟乙基、二氯乙基、三氟乙基、三氯乙基、氯代二氟乙基、四氟乙基、氯代三氟乙基、五氟乙基、氟代丙基、氯丙基、二氟丙基、二氯丙基、三氟丙基、三氯丙基、氰基甲基、氰基乙基、氰基丙基、氰基丁基、羧基甲基、羧基乙基、羧基丙基、羧基丁基、甲氧基甲基、乙氧基甲基、丙氧基甲基、甲氧基乙基、乙氧基乙基、丙氧基乙基、甲氧基丙基、乙氧基丙基、丙氧基丙基、甲氧基羰基甲基、乙氧基羰基甲基、丙氧基羰基甲基、甲氧基羰基乙基、乙氧基羰基乙基、丙氧基羰基乙基、甲氧基羰基丙基、乙氧基羰基丙基、丙氧基羰基丙基、1-丙烯-3-基(烯丙基)、3-甲基-1-丙烯-3-基、2-丁烯-4-基(丁烯基)、1-丙炔-3-基(炔丙基)、3-甲基-1-丙炔-3-基、2-丁炔-4-基、环丙基、氰基环丙基、羧基环丙基、二氟环丙基、二氯环丙基、甲基环丙基、甲氧基羰基环丙基、乙氧基羰基环丙基、环丁基、氰基环丁基、羧基环丁基、二氟环丙基、三氟环丁基、四氟环丁基、氯代三氟环丁基、甲基环丁基、环戊基、氰基环戊基、羧基环戊基、氟代环戊基、氯代环戊基、二氟环戊基、二氯环戊基、甲基环戊基、甲氧基羰基环戊基、乙氧基羰基环戊基、环己基、氰基环己基、羧基环己基、氟代环己基、氯代环己基、二氟环己基、二氯环己基、甲基环己基、三氟甲基环己基、甲氧基羰基环己基、乙氧基羰基环己基、环丙基甲基、二氟环丙基甲基、二氯环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、氰基环己基甲基、羧基环己基甲基、氟代环己基甲基、氯代环己基甲基、甲基环己基甲基、三氟甲基环己基甲基、苯基、氰基苯基、羧基苯基、硝基苯基、氟代苯基、氯代苯基、溴代苯基、甲基苯基、三氟甲基苯基、甲氧基苯基、二氟甲氧基苯基、三氟甲氧基苯基、甲氧基羰基苯基。乙氧基羰基苯基、苄基、氰基苄基、羧基苄基、氟代苄基、氯代苄基、甲基苄基、三氟甲基苄基、甲氧基苄基、二氟甲氧基苄基、三氟甲氧基苄基、甲氧基羰基苄基、乙氧基羰基苄基、苯乙基、呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、氧杂环丁烷基(oxetanyl)、噁唑基、异噁唑基。第2组R2 具有例如上文第1组中列出的定义。第3组R2 具有例如上文第1组中列出的定义。第4组R2 具有例如上文第1组中列出的定义。第5组R2 具有例如上文第1组中列出的定义。第6组R2 具有例如上文第1组中列出的定义。第7组R2 具有例如上文第1组中列出的定义。第8组R2 具有例如上文第1组中列出的定义。第9组R2 具有例如上文第1组中列出的定义。第10组R2 具有例如上文第1组中列出的定义。第11组R2 具有例如上文第1组中列出的定义。第12组R2 具有例如上文第1组中列出的定义。第13组R2 具有例如上文第1组中列出的定义。第14组R2 具有例如上文第1组中列出的定义。第15组R2 具有例如上文第1组中列出的定义。第16组R2 具有例如上文第1组中列出的定义。第17组R2 具有例如上文第1组中列出的定义。第18组R2 具有例如上文第1组中列出的定义。第19组R2 具有例如上文第1组中列出的定义。第20组R2 具有例如上文第1组中列出的定义。
例如,使用1-(4-氰基-2,5-二氟-苯基)-3,6-二氢-2,6-二氧代-5-氯-4-二氟甲基-3-甲基-1(2H)-嘧啶和乙醇钾为起始物,用下面的反应式可以详细说明本发明方法(a)的反应过程:
例如,使用1-(2-氯代-4-氰基-5-甲基硫基-苯基)-3,6-二氢-2,6-二氧代-4-氯代二氟甲基-5-甲基-1(2H)-嘧啶和溴甲烷作起始物,用下面的反应式可以详细说明本发明方法(b)的反应过程:
式(II)提供了在制备式(I)化合物的本发明方法中要用作起始物的取代的卤代苯基尿嘧啶的通式定义。在式(II)中,R1、R3、R4和R5各优选或特别具有上文描述要制备的本发明式(I)化合物中已经指明的优选或特别优选的R1、R3、R4和R5的定义;X优选代表氟、氯或溴,特别是氟。
式(II)起始物是已知的和/或可以通过实质上已知的方法制备(EP-648749,制备实施例)。
式(III)提供了在本发明方法中制备式(I)化合物也是用作起始物的亲核化合物的通式定义。在式(III)中,Q和R2各优选或特别具有上文在描述要制备的本发明式(I)化合物中已经指明的优选的或特别优选的的Q和R2的定义;M优选代表氢、锂、钠或钾,特别是氢、钠或钾。
式(III)的起始物是用于合成的已知的化合物。
制备式(I)化合物的本发明方法(a)优选在合适的反应助剂的存在下进行。合适的反应助剂一般是常规的无机或有机碱或酸受体。这样的助剂优选包括碱金属或碱土金属的乙酸盐、氨基化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇化物,例如乙酸钠、乙酸钾或乙酸钙,氨基锂、氨基钠、氨基化钾或氨基化钙、碳酸钠、碳酸钾或碳酸钙、碳酸氢钠、碳酸氢钾或碳酸氢钙,氢化锂、氢化钠、氢化钾或氢化钙、氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙、甲醇钠或甲醇钾、乙醇钠或乙醇钾,正-或异-丙醇钠或正-或异-丙醇钾、正-、异-、仲-或叔丁醇钠或正-、异-、仲-或叔丁醇钾;还进一步包括碱性有机氮化合物,例如,三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙基胺、N,N-二甲基-环己基胺、二环己基胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基-苯甲胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基和3,5-二甲基-吡啶、5-乙基-2-甲基-吡啶、4-二甲基氨基吡啶、N-甲基哌啶、1,4-二氮杂双环〔2,2,2〕-辛烷(DABCO)、1,5-二氮杂双环〔4,3,0〕-壬-5-烯(DBN)和1,8-二氮杂双环〔5,4,0〕-十一-7-烯(DBU)。
本发明制备式(I)化合物的方法(a)优选在一种稀释剂的存在时进行。合适的稀释剂一般是常规有机溶剂。这样的稀释剂优选包括脂肪族、 脂环族或芳香族,可有可无地被卤化的烃,例如戊烷、己烷、庚烷、石油醚、粗汽油、苯、甲苯、二甲苯、氯苯、二氯苯、环己烷、甲基环己烷、二氯甲烷、三氯甲烷(氯仿)或四氯化碳;二烷基醚,例如,二乙醚、二异丙基醚、甲基叔丁基醚(MTBE)、乙基叔丁基醚、甲基叔戊基醚(TAME)、乙基叔戊基醚、四氢呋喃(THF)、1,4-二噁烷、乙二醇二甲基醚或乙二醇二乙基醚、二乙二醇二甲基醚或二乙二醇二乙基醚;二烷基酮,例如丙酮、丁酮(甲基乙基酮)、甲基异丙基酮或甲基异丁基酮;腈,例如乙腈、丙腈、丁腈或苄腈;酰胺,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-N-甲酰苯胺、N-甲基-吡咯烷酮或六甲基磷酰三胺;酯,例如乙酸甲酯、乙酸乙酯、乙酸正-或异-丙酯、乙酸正-、异-或仲丁酯;亚砜,例如,二甲亚砜;醇,例如甲醇、乙醇、正-或异-丙醇、正-、异-、仲-或叔丁醇、乙二醇一甲基醚或乙二醇一乙基醚、二乙二醇一甲基醚或二乙二醇一乙基醚;或它们与水或纯水的混合物。
当进行本发明方法(a)时,反应温度可以在相当宽的范围内变化。一般情况下,使用的温度在0℃和200℃之间,优选在10℃和150℃之间。
本发明方法(a)一般在大气压下进行,但是本发明方法也可以在高压或低压下进行-一般在0.1巴和10巴之间。
为了进行本发明方法(a),一般以大约等摩尔量使用起始物。但是其中一种起始物也可以以相当大的过量使用。反应一般在反应助剂的存在下在合适的稀释剂中进行,反应混合物一般在所需温度下搅拌几小时。根据常规方法(参见制备实施例)进行后处理。
式(Ia)提供了在用于制备式(I)化合物的本发明方法(b)中用作起始物的取代的氰基苯基尿嘧啶的通式定义。在式(Ia)中,Q、R1、R2、R3和R4各优选或特别具有上文在描述本发明制备的式(I)化合物中已指明的优选的或特别优选的的Q、R1、R2、R3和R4的定义。
式(Ia)的起始物是本发明新的化合物,其可以用本发明方法(a)制备。
本发明方法(b)使用一种烷基化试剂进行。本说明书中烷基化试剂优选是可有可无地被氟-、氯-或C1-C4-烷氧基-取代的、各种情况下最多具有6个碳原子的烷基卤化物,链烯基卤化或炔烃基卤化物(特别是氯化物、溴化物或碘化物),或者是在烷基部分最多有6个碳原子的硫酸二烷基酯。这些化合物从合成方面讲是已知的化合物。
用于制备式(I)化合物的本发明方法(b)优选在一种合适的反应助剂的存在下进行。合适的反应助剂一般是常规的无机或有机碱或酸受体。这样的助剂优选包括碱金属或碱土金属的乙酸盐、氨基化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇化物,例如乙酸钠、乙酸钾或乙酸钙,氨基化锂、氨基化钠、氨基化钾或氨基化钙、碳酸钠、碳酸钾或碳酸钙、碳酸氢钠、碳酸氢钾或碳酸氢钙,氢化锂、氢化钠、氢化钾或氢化钙、氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙、甲醇钠或甲醇钾、乙醇钠或乙醇钾,正-或异-丙醇钠或正-或异-丙醇钾、正-、异-、仲-或叔丁醇钠或正-、异-、仲-或叔丁醇钾;还进一步包括碱性有机氮化合物,例如,三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙基胺、N,N-二甲基-环己基胺、二环己基胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基-苯甲胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基和3,5-二甲基-吡啶、5-乙基-2-甲基-吡啶、4-二甲基氨基吡啶、N-甲基哌啶、1,4-二氮杂双环〔2,2,2〕-辛烷(DABCO)、1,5-二氮杂双环〔4,3,0〕-壬-5-烯(DBN)和1,8-二氮杂双环〔5,4,0〕-十一-7-烯(DBU)。
制备式(I)化合物的本发明方法(b)优选在一种稀释剂的存在下进行。合适的稀释剂一般是常规有机溶剂。这样的稀释剂优选包括脂肪族、脂环族或芳香族的、可有可无地被卤化的烃,例如戊烷、己烷、庚烷、石油醚、粗汽油、苯、甲苯、二甲苯、氯苯、二氯苯、环己烷、甲基环己烷、二氯甲烷、三氯甲烷(氯仿)或四氯化碳;二烷基醚,例如,二乙醚、二异丙基醚、甲基叔丁基醚(MTBE)、乙基叔丁基醚、甲基叔戊基醚(TAME)、乙基叔戊基醚、四氢呋喃(THF)、1,4-二噁烷、乙二醇二甲基醚或乙二醇二乙基醚、二乙二醇二甲基醚或二乙二醚二乙基醚;二烷基酮,例如丙酮、丁酮(甲基乙基酮)、甲基异丙基酮或甲基异丁基酮;腈,例如乙腈、丙腈、丁腈或苄腈;酰胺,例如N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N-甲基-N-甲酰苯胺、N-甲基-吡咯烷酮或六甲基磷酰三胺;酯,例如乙酸甲酯、乙酸乙酯、乙酸正-或异-丙酯、乙酸正-、异-或仲丁酯;亚砜,例如,二甲亚砜;醇,例如甲醇、乙醇、正-或异-丙醇、正-、异-、仲-或叔丁醇、乙二醇一甲基醚或乙二醇一乙基醚、二乙二醇一甲基醚或二乙二醇一乙基醚;或它们与水或纯水的混合物。
当进行本发明方法(b)时,反应温度可以在相当宽的范围内变化。一般情况下使用的温度在0℃和150℃之间,优选在10℃和120℃之间。
本发明方法(b)一般在大气压下进行,但是也可以在高压或减压下进行该方法-一般在0.1巴和10巴之间。
为了进行本发明方法(b),一般以大约等摩尔量使用起始物。但是也可以以相当大的过量使用其中一种起始物。反应一般在反应助剂的存在下在一种合适的稀释剂中进行,反应混合物一般在所需温度下搅拌几小时。根据常规方法(参见制备实施例)进行处理。
本发明活性化合物可以用作脱叶剂、干燥剂、茎叶杀伤剂、特别是作为杂草杀伤剂。从广义上来说,所谓杂草被理解为在不期望其生长的地点生长的所有植物。本发明物质是作为共除草剂还是作为选择性除草剂主要取决于所使用的量。
例如与下面的植物相关可以使用本发明活性化合物:双子叶杂草种类:芥属(Sinapis)、独行菜属(Lepidium)、猪殃殃属(Galium)、繁缕属(Stellaria)、母菊属(Matricaria)、春黄菊属(Anthemis)、辣子属(Galinsoga)、黎属(Chenopodium)、荨麻属(Urtica)、千里光属(Senecio)、苋属(Amaranthus)、马齿苋属(Portulaca)苍耳属(Xanthium)、旋芯属(Convolvulus)、甘薯属(Ipomoea)、蓼属(Polygonum)、田菁(Sesbania)、豚草属(Ambrosia)、蓟属(Cirsium)、飞廉属(Carduus)、苦苣菜属(Sonchus)、茄属(Solanum)、焊菜属(Rorippa)、水松叶属(Rotala)、母草属(Lindernia)、野芝麻属(Lamium)、婆婆纳属(Veronica)、苘麻属(Abutilon)、刺果(Einex)、曼陀罗属(Patura)堇菜属(Viola)、鼬瓣芯属(Galeopsis)、罂粟属(Papaver)、矢车菊属(Centaurea)、车轴草属(Trifolium)、毛茛属(Ranunculus)和蒲公英属(Taraxacum)。双子叶作物种类:棉属(Gossypium)、Glycine、Beta、胡萝卜属(Daucus)、菜豆属(Phaseolus)、Pisum、茄属(Solanum)、亚麻属(Linum)、甘薯属(Ipomoea)、巢菜属(Vicia)、烟草属(Nicotiana)、番茄(Lycopersicon)、花生(Arachis)、芥属(Brassica)莴苣属(Lactuca)、cucumis,和臭瓜(Cucurbita)。单子叶杂草种类:稗属(Echinochloa)、狗尾草属(Setaria)、黍属(Panicum)、马唐属(Digitaria)、梯牧草(Phleum)、早熟禾属(Poa)、羊茅属(Festuca)、蟋蟀草属(Eleusine)、臂形草属(Brachiaria)、黑麦草属(Lolium)、雀麦属(Bromus)、燕麦属(Avena)、莎草属(Cyperus)、蜀黍属(Sorghum)、冰草属(Agropyron)、Cycnodon、雨久花属(Monochoria)、飘拂草属(Fimbristylis)、慈姑(Sayittaria)、荸荠属(Eleocharis)、草(Scirpus)、雀稗草(Paspalum)、Ischaemum、尖瓣芯属(Sphenoclea)、龙爪茅属(Dactyloctenium)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)和Apera。单子叶作用种类:稻属(Oryza)、Zea、Triticum、大麦属(Hordeum)、燕麦属(Avena)、黑麦属(Secale)、蜀黍属(Sorghum)、黍属(Panicum)、甘蔗(Saccharum)、波罗(Ananas)、Asparagus和葱属(Allium)。
但是,本发明活性化合物的用途无论如何不受这些种类的限制,也以相同方式扩展到其它植物。
根据浓度,本发明化合物适于例如在工业领域和铁路轨道,跑道上,以及有或没有种植树的广场上完全控制杂草。同样,本发明化合物可以用来控制多年生耕作中的杂草,例如森林、装饰性种植的树、果园、葡萄园、柑桔林、坚果园、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油棕种植园、可可种植园、软果种植和蛇麻草田、草坪、赛马场和牧场,并用来选择性控制年生作物中的杂草。
本发明式(I)化合物特别适用于通过出苗前和出苗后方法选择性控制单子叶或双子叶作物中单子叶和双子叶杂草。
而且,本发明式(I)化合物还具有强的杀虫活性,特别是杀甲虫幼虫,例如辣根猿叶甲幼虫(Phaedon cochleariae)和杀蝶的躅,例如小菜蛾(Plutella xylostella)。
在某种程度上,式(I)化合物也具有杀真菌活性,例如杀稻上的豆黄夜蛾(Pyricularia oryzae)。
具有好的作物耐受性和恒温动物安全性的本发明活性化合物适于控制动物害虫,特别是昆虫、螨和线虫,这些害虫在农业、林业、贮存产品和材料的保护,以及卫生保健部门会碰到。这些化合物优选用作农作物保护剂。它们对一般敏感性和抗性物种有活性,而且对生长的全部阶段或部分阶段有用。上述害虫包括:等足目,例如Onixcus aselluse,鼠妇和porcellio scaber。多足纲的目,例如Blaniulus guttulatus。唇足亚纲的目,例如Geophilus carpophagus和蚰蜒目的种(Scutigeraspec)。综合纲的目,例如Scutigerella immaculata。缨尾目,例如西洋衣鱼(Lepisma saccharina)。弹尾目,例如Onychiurus armatus。
直翅目,例如东方蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、马德拉蠊(Leucophaea maderae)、德国小蠊(Blattellagermanica)、灶马(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoria migratoriordes)、长额负蝗(Melanoplusdifferentialis)和Schistocerca gregaria。革翅目:例如欧洲球螋(Forficula auricularia)。等翅目,例如白蚁属(Reti culitermes spp.)。虱目,例如头虱(Pediculus humanus corporis)、盲虱属(Haematopinus spp.)和长颚虱(Linognathus spp.)。食毛目,例如羽虱属(Trichodectes spp.)和Damalinea spp.。缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Tripstabaci)。异翅亚目,例如褐盾蝽属(Eurygaster spp.)、Dysdercusintermedius、甜菜拟网蝽(Piesma quadrata)、臭虫(Cimexlectularius)、Rhodnius prolixus和吸血猎蝽属(Triatoma spp.)。同翅亚目,例如Aleurodes brassicae、棉粉虱(Bemisia tabaci)、温室白粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevecoryne brassicae)、茶隐瘤额蚜(Cryptomyzusribis)、蚕豆蚜(Aphis fabae)、苹果蚜(Aphis pomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterus arundinis)、Phylloxera vastatrix、瘿绵蚜属(Pemphigus spp.)、Macrosiphumavenae、瘤额蚜(Myzus spp.)、忽布瘤额蚜(Phorodon humuli)、粟缢管蚜(Rhopalosiphum padi)、叶蝉属(Empoasca spp.)、Euscelisbilobatus、黑尾叶蝉(Nephotettix cincticeps)、李蜡蚧(Lecaniumcorni)、油橄榄盔蚧(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(Pslla spp.)。鳞翅目,例如,红铃虫(Pectinophora gossypiella)、松尺蠖(Bupaluspiniarius)、Cheimatobia brumata、Lithocolletis blancardella、樱桃巢蛾(Hyponomeuta padella)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosoma neustria)、Euproctis chrysorrhoea、毒蛾属(Lymantria spp.)、棉叶穿孔潜蛾(Bucculatrix thurberiella)、Phyllocnistis citrella、地老虎(Agrotis spp.)、切根虫(Euxoa spp.)、褐夜蛾(Feltia spp.)、埃及金铜钻(Earias insulana)、夜蛾属(Heliothis spp.)、甜菜夜蛾(Spodoptera exigua)、甘蓝夜蛾(Mamestra brassicae)、Panolis flammea、斜纹夜蛾(Spodopteralitura)、夜蛾属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹果蠹蛾(Carpocapsa pomonella)、粉蝶属(Pieris spp.)、螟属(Chilo spp.)、Pyrausta nubilalis、Ephestia kuehniella、大黄螟(Galleria mellonella)、袋衣蛾(Tineola bisselliella)、衣蛾(Tineapellionella)、褐织叶蛾(Hofmannophila pseudospretella)、Cacoeciapodana、Capua reticulana、云杉卷叶蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶黄卷叶蛾(Homonamaynanima)和栎绿卷叶蛾(Tortrix viridana)。鞘翅目,例如家贝窃蠹(Amobium punctatum)、Rhizoperthadominica、Bruchidius obtectus、大豆象(Acanthoscelidesobtectus)、家天牛(Hylotrupes bajulus)、Ayelastica alni、甲铃薯甲虫(Leptinotarsa decemlineata)、Phaedon cochleariae、叶甲属(Diobrotica spp.)、油菜兰跳甲(Psylliodes chrysocephala)、墨西哥豆瓢虫(Epilachna varivestis)、Atomaria spp.,锯胸谷盗(Oryzaephilus surinamensis)、象甲属(Anthonomus spp.)、米象属(Sitophilus spp)、Otiorrhynchus sulcatus、香蕉蛀基象甲(Cosmopolites sordidus)、Ceuthorrhynchus assimilis、苜蓿叶象甲(Hypera postica)、皮蠹属(Permestes spp.)、皮蠹属(Trogodermaspp.)、皮蠹属(Anthrenus spp.)、黑皮蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、Meligethes aeneus、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptus hdoleucus)、麦蛛甲(Gibbium psylloides)、拟谷盗属(Tribolium spp)、黄粉甲(Tenebrio molitor)、叩甲属(Agriotes spp.)、金针虫属(Conoderus spp.)、Melolonthamelolontha、六月金龟子(Amphiniallon solstitialis)和Costelytrazealandica。膜翅目,例如锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampaspp.)、蚁(Lasius spp.)厨蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。双翅目,例如伊蚊(Aedes spp.)、斑按蚊属(Anopheles spp.)、库蚊(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、家蝇(Musca spp.)、厩蝇(Fannia spp)、红头丽蝇(Calliphoraerythrocephala)、丝光绿蝇属(Lucilia spp.)、Chrysomyia spp.、疽蝇属(Cuterebra spp.)、Gastrophilus spp、Hyppobosca spp.,、来螯蝇属(Stomoxys spp.)、鼻蝇属(Oestrus spp.)、皮蝇属(Hydoderma spp.)、牛虻(Tabanus spp.)、Tannia spp.,Bibiohortulonus、瑞黄麦杆蝇(Oscinella frit)、麦蝇(Phorbia spp.)、甜菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitiscapitata)、油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipulapaludosa)。蚤目,例如东方鼠蚤(Xenopsylla cheopis)和角叶蚤属(Ceratophyllusspp.)。蛛形纲的目,例如,Scorpio maurus和黑寡妇球腹蛛(Latrodectusmactans)。蜱螨目,例如粗脚粉螨(Acarus siro)、隐喙蜱(Argas spp.)、喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、Eriophyes ribis、桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilusspp.)、头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、Hyalomma spp.、硬蜱(Ixodes spp.)、痒螨属(Psoroptes spp.)、羔螨属(Chorioptes spp.)、疥螨(Sarcoptes spp.)、线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、红蜘蜂(Panonychus spp.),和红叶螨属(Tetranychus spp.)。寄生植物线虫包括,短体线虫属(Pratylenchus spp)、Radopholussimilis、起绒草茎线虫(Ditylenchus dipsasi)、半穿刺线虫(Tylenchussemipenetrans)、异皮线虫属(Heterodera spp.)、球异皮线虫属(Globodera spp.)、根结线虫属(Meloidogyne spp.)、渭刃线虫属(Aphelenchoides spp.)、长针线虫属(Longidorus spp.)、剑线虫(Xiphinema spp.),和毛刺线虫属(Trichodorus spp.)。
合适的化合物是例如下面列出的化合物:杀真菌剂:2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟-甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚胺基-N-甲基-2-(2-苯氧基苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-〔6-(2-氰基苯氧基)嘧啶-4-基氧基〕-苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚胺基〔α-(邻甲苯基氧基)-邻-甲苯基〕乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑,苯霜灵、邻碘酰苯胺、苯菌灵、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、敌菌丹、克菌丹、多菌灵、萎锈灵、灭螨猛、地茂散、氯化苦、百菌消、乙菌利、代森盐、霜尿氰、环唑醇、酯菌胺,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、二硝巴豆酸酯、二苯胺、吡菌硫、灭菌磷、二噻农、多果定、联氨噁唑酮,克瘟散、epoxyconazole、乙嘧酚、土菌灵,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、fludioxonil、氟氯菌核利、fluquinconazole、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯钛、麦穗宁、呋霜灵、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、异稻瘟净、(IBP)、异菌脲、稻瘟灵,春雷霉素、铜制剂、例如:氢氧化铜、环烷酸酮、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、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、呋菌胺、代森联、嘧菌胺、腈菌唑,二甲基二硫氨基甲酸镍、nitrothal-isopropyl、氟苯嘧啶醇、甲呋酰胺、噁霜灵、oxamocarb、氧化萎锈灵,稻瘟酯、戊菌唑、戊菌隆、稻病磷、四氯苯酞、多马霉素、病花灵、聚氨基甲酸酯、多氧霉素、烯丙异噻唑、味鲜安、腐霉利、丙酰胺、环丙唑、丙森锌、吡嘧磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯(PCNB),硫和硫制剂,戊唑醇、叶枯酞、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基硫菌灵、福美双、甲苯氟磺胺、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、十三吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核利、代森锌、福美锌、杀细菌剂:bronopol、双氯酚、氯甲基吡啶、二甲基二硫氨基甲酸镍、春雷霉素、异噻菌酮、呋喃羧酸、oxyteracycline、烯异丙噻唑、链霉素、叶枯酞、硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:墩螨素、AC 303 630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双虫脒、Avermectin、AZ 60541、azadirachtin、保棉磷、三唑锡,苏云金杆菌、噁虫威、丙硫克百威、杀虫磺、氟氯氰菊酯、氟氯菊酯、BPMC、brofenprox、溴硫磷、合杀威、噻嗪酮、丁酮威、butylpyridaben,硫线磷、甲萘威、克百威、三硫磷、丁硫克百威、杀螟丹、CGA 157419、CGA 184699、chloethocarb、chlorethoxyfos、毒虫畏、定虫隆、氯甲硫磷、甲基毒死蜱、毒死蜱、顺式-苄呋菊酯、clocythrin、四螨嗪、杀螟腈、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、酚线磷、敌敌畏、dicliphos、百治磷。、乙硫磷、除虫脲、乐果、甲基毒虫畏、敌噁磷、乙拌磷,克瘟散、emamectin、高氰戊菊酯、乙硫苯威、乙硫磷、醚菊酯、灭线磷、乙嘧硫磷,虫胺磷、硅螨醚、苯乙锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、fipronil、吡氟禾草灵、氟螨脲、氟氰戊菊酯、氟虫脲、氟胺氰菊酯、地虫硫、安果、噻唑磷、fubfenprox、呋线威、HCH、庚烯磷、氟铃脲、噻螨酮,吡虫啉、异稻瘟净、氯唑磷、异丙胺磷、叶蝉散、噁唑磷、ivermectin、氯氟氰菊酯、lufenuron、马拉硫磷、灭蚜蜱、速灭磷、mesulfenphos、螨牛故、虫螨畏、甲胺磷、杀扑磷、灭梭威、灭多威、速灭威、milbemectin、久效磷、moxidectin,二溴磷、MC184、NI25、nitenpyram,氧乐果、杀线威、亚砜吸磷、异砜磷,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、抗蚜威、甲基嘧啶磷、嘧啶磷A、丙溴磷、猛杀威、丙虫磷、残杀威、丙磷磷、发果、pymerozin、吡唑硫磷、pyradaphenthion、pyresmethrin、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH5992,蔬果磷、sebufos、silafluofen、治螟磷、甲丙硫磷,tebufenozid、tebufenpyrad、tebupirimiphos、伏虫隆、七氟菊酯、双硫磷、持灭威、特丁磷、杀虫畏、thiafenox、硫双威、久效威、二甲硫吸磷、虫线磷、thuringiensin、四溴菊酯、苯噻螨、三唑磷、triazuron、敌百虫、杀虫隆、混灭威,蚜灭多、XMC、灭杀威、YI5301/5302、zetamethrin。
也可能是与其它已知的活性化合物例如除草剂或者与肥料和生长调节剂的混合物。
本发明活性化合物另外可以以商售制剂和以由这些制剂制备的使用形式存在,作为与增效剂的混合物。增效剂是增强活性化合物作用的化合物,要加入的增效剂其自身不需要是活性的。
由商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。该使用形式的活性化合物浓度是0.0000001至95%重量的活性化合物,优选0.0001至1%重量比。
本发明化合物以适合于使用形式的常规方式使用。
当用来杀灭卫生保健领域的害虫和贮存产品的害虫时,本发明化合物对木材和粘土有极好的残留作用以及好的对用石灰处理过的底物上的碱性的稳定性。
本发明活性化合物不只具有杀植物和卫生领域害虫和贮存产品的害虫的作用,而且在兽药领域也有杀动物寄生物(外寄生虫)的作用,所述寄生虫例如硬蜱、软蜱、疥螨、秋蟑、蝇(叮和吮),寄生的蝇幼虫、虱、头虱和皮革虱和蚤。这些寄生虫包括:虱目(Anoplurida),例如血虱属(Haematopinus spp.)、长颚虱(Linognathus spp.)、虱属(pediculus spp.)阴虱属(Phtirus spp.)管虱属(Solenopotes spp.)。食毛目咬虱(Mallophagida)和Amblycerina及Ischnocerina亚目,例如毛羽虱属(Trimenopon spp.)、Menopon spp.、巨羽虱属(Trinotonspp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentronspp.、Damalina spp.、Trichodectes spp.、Felicola spp.。双翅目和长角亚目(Nematocerina)和Brachycerina亚目,例如伊蚊、斑按蚊属、库蚊、蚋属(Simulium spp.)、全毛真蚋(Eusimuliumspp.)、白蛉(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓(Culicoides spp.)、斑虻(Chrysops spp.)、瘤虻(Hybomitraspp.)、Atyltus spp.、虻(Tabanus spp.)、麻虻(Haematopota spp.)Philipomyia spp.、Braula spp.、Musca spp.、齿股蝇属(Hydrotaeaspp.)、螫蝇(Stomoxys spp.)、Haematobia spp.、Morellia spp.、厕蝇(Fannia spp.)、Glossina spp.、Calliphora spp.、Luciliaspp.、Chrysomyia spp.、Wohlfahrtia spp.、别麻蝇(Sarcophayaspp.)、Oestrus spp.、皮蝇(Hypoderma spp.)、Gasterophilus spp.、虱蝇(Hippobosca spp.)、Lipoptena spp.和Melophayus spp.。蚤目,例如蚤属(Pulox spp.)、Ctenocephalides spp.、鼠蚤(Xenopsylla spp.)和角叶蚤(Ceratophyllus spp.)。异翅亚目,例如臭虫属(Cimex spp.)、吸血猪蝽属(Triatoma spp.)、Rhodnius spp.和全圆蝽属(Panstrongylus spp.)。蠊目(Blattarida),例如东方蠊、美洲大蠊、德国小蠊、蠊属(Supella spp.)。螨亚类(Acarida)和后胸气门目(Metastigmata)和中胸气门目(Mesostigmata),例如隐喙蜱属、喙蜱属、耳残喙蜱(Otobius spp.)、硬蜱、花蜱属、牛蜱属、矩头蜱(Dermacentor spp.)、Haemophysalisspp.、璃眼蜱(Hyalomma spp.)、头蜱属、鸡皮刺螨、瑞立绦虫(Raillietiaspp.)、Pneumonyssus spp.、Sternostoma spp.和Varroa spp.。Actinedida(恙螨亚目,Prostigmata)和Acaridida(Astigmata),例如Acarapis spp.、姬螯螨属(Cheyletiella spp.)、Ornithocheyletiaspp.、Myobia spp.、疥螨(Psorergates spp.)、蠕形螨(Demodoxspp.)、恙螨(Trombicula spp.)、牦螨(Listrophorus spp.)、粗脚粉螨(Acarus spp.)、酪螨(Tyrophagus spp.)、嗜木螨(Caloglyphusspp.)Hypodectes spp.、翼衣螨属(Pterolichus spp.)、痒螨(Psoroptesspp.)、痒螨(Chorioptes spp.)、Octodectes spp.、疥螨(Sarcoptesspp.)、Notoedres spp.、足螨(Knemidocoptes spp.)、Cytodites spp.和Laminosioptes spp.。
本发明式(I)化合物也适于杀死侵染农业生产家畜的节肢动物门,所述家畜例如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂,其它宠物,例如狗、猫、鸶养鸟和鱼缸养殖鱼和试验用动物,例如,仓鼠、豚鼠、大鼠和小鼠。通过杀死这些节肢动物,可以避免家畜死亡并避免产品量的减少(产品例如肉、奶、羊毛、皮革、蛋、蜂蜜等),因此通过使用本发明活性化合物可能实现更经济更简单的动物的科学管理。
在兽医领域本发明活性化合物以已知方式通过肠给药,例如以片剂、胶囊、顿服水剂、顿服药、颗粒剂、糊剂、巨丸剂、通过进食方法和栓剂的形式,通过肠胃外给药,例如通过注射(肌内、皮下、静脉内、腹膜内等)、埋入,通过鼻给药,通过以例如浸渍或浸浴、喷洒、倒施和点施、洗用和撒粉的形式皮肤使用,也可以借助于含有活性化合物的用模子做的物品,例如颈圈、耳饰、尾饰、腿带、笼头、标记物等,而使用。
当对牲畜、家禽、宠物等使用时,本发明式(I)活性化合物可以作为以1至80%重量比的量含有活性化合物的制剂(例如粉末剂、乳剂、可流动的组合物)而被使用,直接使用或者稀释100至1000倍之后使用,或者可以用作化学浴。
另外还发现本发明式(I)化合物还具有杀破坏工业物质的昆虫的有潜力的杀虫作用。
优选作为例子可以提到下面的昆虫-但不受此限制:甲虫,例如家天牛(Hylotrupes bajulus)、Chlorophorus pilosis、家具窃蠹(Anobium punctatum)、Xestobium rufovillosum、Ptilinuspecticornis、Dendrobium pertinox、Ernobius mollis、Priobiumcarpini、欧洲竹粉蠹(Lyctus brunneus)、Lyctus africanus、平颈粉蠹(Lyctus planucollis)、Lyctus linearis、Lyctus pubescens、Trogoxylon aequale、Minthes rugicollis、小蠹虫种(Xyleborusspec.)、Tryptodendron spec.、Apate monachus、Boserychuscapucins、Heterobostrychus branneus、Sinoxylon spec和竹长蠹(Dinoderus minutus)。膜翅目(Hymen opterans),例如钢青小树蜂(Sirex juvencus)、枞大树蜂(Urocerus gigas)、Urocerusgigas和Urocerus augur。白蚁,例如Kalotermes flavicollis、Cryptotermes brevis、Heterotermesindicola、Retioulitermes flavipes、Reticulitermes santonensis、Reticulitermes lucifugus、澳洲白蚁(Mastotermes darwiniensis)、Zootermopsis nevadensis和台湾家白蚁(Coptotermes formosanus)。Bristle-ails,例如西洋衣鱼。
本发明中所涉及的工业材料理解为非生命材料,例如优选合成材料,粘合剂,胶料,纸,纸板,皮革,木材和木材加工产品以及涂料。
要保护使不受昆虫侵染的材料特别优选的是木材和木材加工产品。
可以用本发明组合物或含有这样一种组合物的混合物保护的木材和木材加工产品理解为包括,例如:建筑用木料、木梁、铁路枕木、桥梁用料、船跳板、木制运载工具、板条箱、制模板、容器、电线柱、木制套板、木制窗、门、胶合板、废纸制成的纸板、细木制品或房屋建设或建筑细木工行业中常用的木制品。
活性化合物可以其本身、以浓缩物或常规制剂形式例如粉剂、颗粒剂、溶液、混悬剂、乳液或糊剂而被使用。
所述制剂可以用实质上已知的方法制备,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、水相斥剂,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助剂混合。
用于保护木材和木制材料的杀虫组合物或浓缩物以0.0001至95%重量比,特别是0.001至60%重量浓度含有本发明活性化合物。
使用的组合物或浓缩物的量取决于害虫物种,和虫害发生的情况以及虫害所发生的基质。各种情况下通过系列试验测定施用的最佳比例。但是,一般情况下,以要保护的材料为基础,使用0.0001至20%重量,优选0.001至10%重量活性化合物就足够了。
使用的溶剂和/或稀释剂是一种有机化学溶剂或溶剂混合物和/或低挥发性的油性或油型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/或水以及如果需要,一种乳化剂和/或湿润剂。
优选使用的有机化学溶剂是具有蒸发系数大于35,闪点高于30℃,优选高于45℃的油状或油型溶剂。可以用作这样的具有低挥发性且在水中不溶解的油状和油型溶剂的物质是合适的矿物油或其芳香级分,或者是含矿物油的溶剂混合物,优选石油溶剂、石油和/或烷基苯。
有利使用的物质是沸点范围是170至220℃的矿物油,沸点范围在170至220℃的石油溶剂,沸点范围在250至350℃的锭子油,沸点范围在160至280℃的石油醚或芳烃、松节油香料等等。
在一个优选的实施方案中,使用了沸点范围在180至210℃的液体脂肪烃,或沸点范围在180至220℃的芳烃和脂肪烃的高沸点混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
具有蒸发系数大于35且闪点高于30℃,优选高于45℃的低挥发性有机油状或油型溶剂可以部分被高度或中等挥发性的有机化学溶剂替代,条件是该溶剂混合物也具有大于35的蒸发系数和高于30℃,优选高于45的闪点,并且杀虫剂/杀真菌剂混合物在该溶剂混合物中是可溶解的或可乳化的。
在一个优选的实施方案中,有机化学溶剂或溶剂混合物的一部分由脂肪族极性有机化学溶剂或溶剂混合物代替。优选使用的物质是具有羟基和/或酯基和/或醚基的脂族有机化学溶剂,例如乙二醇醚、酯等等。
本发明范围中使用的有机化学粘合剂是实质上已知的合成树脂和/或粘合干性油,并且可以用水稀释和/或在使用的有机化学溶剂中是可溶解的或可分散的或可乳化的,具体地说,含有下面的物质或者由下面的物质组成的粘合剂:丙烯酸树脂、乙烯树脂,例如聚乙酸乙烯酯树脂、聚酯树脂、缩聚树脂、加聚树脂、聚亚胺酯树脂、醇酸树脂或改性的醇酸树脂、酚醛树脂、烃类树脂,例如茚/苯并呋喃树脂、有机硅树脂、以天然和/或合成树脂为基础的干性植物油和/或干性油和/或物理干性粘合剂。
用作粘合剂的合成树脂可以以乳剂,分散剂或溶液的形式使用。最多为10%重量的沥青或沥青状物质可以用作粘合剂。另外也可以使用实质上已知的着色剂,颜料,水排斥剂,调味物质和抑制剂或防腐剂。
根据本发明,所述组合物或浓缩物优选含有至少一种醇酸树脂或改性的醇酸树脂和/或干性植物油作为有机化学粘合剂。根据本发明优选使用的是油含量超过45%重量,优选50至68%重量的醇酸树脂。
所有或其中的一些上述粘合剂可以用固定剂(混合物)或增塑剂(混合物)代替。这些添加剂是为了防止活性化合物挥发和结晶或沉淀。优选的是它们代替粘合剂的0.01至30%(以使用的100%粘合剂为基础)。
增塑剂来自苯二甲酸酯类化学品,例如苯二甲酸二丁酯、苯二甲酸二辛酯或苯二甲酸苄酯丁酯、磷酸酯,例如磷酸三丁酯,己二酸酯,例如己二酸二(2-乙基己基)酯,硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯,油酸酯,例如油酸丁酯,丙三醇醚,或相对高分子量的乙二醇醚、丙三醇酯和对甲苯磺酸酯。
固定剂在化学上以聚乙烯烷基醚为基础,例如聚乙烯甲基醚,或以酮为基础,例如二苯甲酮或亚乙基二苯甲酮。
特别适合作为溶剂或稀释剂的还有水,如果合适,作为与一种或几种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
通过大规模工业化浸渍方法,例如真空,双倍真空或加压方法实现木材的特别有效的保护。
如果合适,即用型组合物可以另外含有一种或几种其它杀虫剂,和,如果合适,另外含有一种或几种杀真菌剂。
可以混合的合适的其它成分优选是WO 94/29268中提到的杀虫剂和杀真菌剂。该文献中提到的化合物引入到本申请中作为参考。
可以混合的特别优选的成分是杀虫剂,例如毒死蜱、辛硫磷、Silafluofin、甲体氯氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、NI-25、氟虫脲、氟铃脲和杀虫隆。和杀真菌剂,例如epoxyconazole、己唑醇、戊环唑、环丙唑、戊唑醇、环唑醇、metconazole、抑霉唑、苯氟磺胺、甲苯氟磺胺、氨基甲酸3-碘-2-丙炔基丁酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
活性化合物可以配制成常规制剂,例如溶液、乳液、可湿粉剂、混悬剂、粉剂、细粉剂、糊剂、可溶性粉剂、颗粒剂、混悬乳油、用活性化合物浸渍的天然的和合成材料,聚合物质中非常细的胶囊。
这些制剂以已知方法制备,例如将活性化合物与增充剂混合,所述增充剂是液体溶剂和/或固体载体,可有可无地使用表面活性剂,即,是乳化剂和/或分散剂和/或发泡剂。
在使用水作为增充剂的情况下,例如,可以使用有机溶剂作为助剂溶剂。合适的液体溶剂主要是:芳烃,例如二甲苯、甲苯或烷基萘、氯代芳烃和氯代脂烃,例如氯苯、氯乙烯或二氯甲烷,脂肪烃,例如环己烷或石蜡,例如石油级分,矿物油和植物油,醇,例如丁醇或乙二醇及其醚和酯,酮,例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂,例如二甲基甲酰胺和二甲亚砜,还有水。
合适的固体载体是:例如铵盐和研细的天然矿物,例如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和研细的合成矿物,例如高度分散的硅石、矾土和硅酸盐,作为用于颗粒剂的固体载体,合适的有:例如粉碎了的和分选的天然岩石,例如方解石、大理石、浮石、海泡石和白云石,以及合成的无机和有机粉颗粒,和有机材料的颗粒,例如木屑、花生壳、玉米芯和烟草梗;作为乳化剂和/或发泡剂合适的有:例如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚、磺酸烷基酯、硫酸烷基酯、磺酸芳基酯,以及蛋白质水解产物;作为分散剂合适的有:例如木素亚磺酸废液和甲基纤维素。
制剂中可以使用增粘剂,例如羧甲基纤维素和粉末,颗粒或胶乳形式的天然的和合成的聚合物,例如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,例如脑磷脂和卵磷脂,和合成的磷脂。其它的添加剂可以是矿物油和植物油。
可以使用着色剂,例如无机颜料,例如氧化铁、氧化钛和普鲁氏蓝,和有机染料,例如茜素染料、偶氮染料和金属酞菁染料和痕量营养成分,例如铁盐、锰盐、硼盐、钴盐、钼盐和锌盐。
一般情况下制剂含有0.1至95%重量比的活性化合物,优选在0.5和90%之间。
本发明活性化合物可以直接使用或者作为与已知的控制杂草的除草剂的混合物制剂使用,可以是即用型制剂或容器混合物。
用于混合物的合适的共存成分是已知的除草剂,例如苯胺类,例如吡氟草胺和敌稗;芳堇羧酸,例如二氯吡啶酸、dicamba和毒莠定;芳基氧基链烷酸,例如2,4-D、2,4-DB、2,4-DP、氟草烟、MCPA、MCPP和绿草定;芳基氧基-苯氧基-链烷酸酯,例如禾草灵、噁唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵;吖嗪酮(azinones),例如杀草敏和哒草伏;氨基甲酸酯,例如氯苯胺灵,甜菜安、甜菜宁和苯胺灵;乙酰氯苯胺,例如甲草胺、乙草胺、丁草胺、吡草胺、丙草安、丙草胺和毒草胺;二硝基苯胺,例如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类,例如三氟羧甲醚、甲羧除草醚、乙羧氟草醚、氟草胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲,例如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和甲基苯噻隆;羟胺类,例如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类,例如味草烟、味草酯、灭草烟和灭草喹;腈类,例如溴苯腈、敌草腈、碘苯腈;氧化乙酰胺类,例如苯噻草胺;磺酰脲类,例如amidosulfuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆、醚苯黄隆和苯黄隆;氨基甲酸硫羟酯类,例如丁草特、灭草特、野燕畏、EPTC、禾草畏、草达灭、苄草丹、杀草丹和野燕畏;三嗪类,例如莠、去津、氰草津、西玛津、西玛通、特丁净,和terbutylazine;三嗪酮类,例如环嗪酮、苯嗪草酮、嗪草酮;其它,例如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵膦、草甘膦、isoxaben、哒草特、二氯喹啉酸、喹草酸、草硫磷和灭草环。
也可以是与其它已知活性化合物,例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂,驱鸟剂、植物营养剂和改善土壤结构的试剂的混合物。
活性化合物可以其本身、以其制剂形式或通过进一步稀释而由其制备的使用形式来使用,例如即用型溶液、混悬剂、乳剂、粉剂、糊剂和颗粒剂。也可以以常规方式使用,例如通过灌溉、喷雾、雾化或播撒。
本发明活性化合物可以在出苗前或出苗后使用。也可以在耕作前加入到土壤中。
使用的活性化合物的量可以在一个基本范围内变化。主要取决于所期望的效果的性质。一般情况下,使用的量是每公顷土壤表面施用1g至10kg活性化合物,优选5g至5kg/公顷。
3.8g(12mmol)1-(4-氰基-2,5-二氟-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1-(2H)-嘧啶,1.5g(21mmol)甲醇钠和50mlN-甲基-吡咯烷酮在130℃搅拌36小时。混合物冷却后,用乙酸乙酯稀释至大约三倍体积,用水洗涤混合物,在硅胶柱上色谱分离产物(环己烷/乙酸乙酯,Vol:1/1)。
1.5g(4mmol)1-(4-氰基-2-氟-5-甲氧基-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶,0.6g(5mmol)硫酸二甲酯,0.7g(5mmol)碳酸钾和100ml乙腈回流下加热18小时,然后用水泵抽真空浓缩。残余物溶解于水/乙酸乙酯,并分离有机相,用硫酸钠干燥过滤。用水泵抽真空浓缩滤液,残余物溶解于乙酸乙酯/二异丙基醚,抽滤分离所得结晶产物。
得到1.0g(理论值73%)1-(4-氰基-2-氟-5-甲氧基-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点:155℃。
通过实施例1和2的方法并根据本发明制备方法的概括描述,也可以制备例如下面表1中列出的式(I)化合物。表1:式(I)化合物的实施例实施例
Q R1 R2 R3 R4 R5序号
熔点(℃)3 S H CH2C6H5 H CF3 CH3 884 O F CH2C6H5 H CF3 CH3 45
熔点(℃)7 S F
H CF3 CH38 S F
CH3 CH3 CH39 S F
H CF3 CH310 S F
CH3 CF3 CH311 S F
H CF3 CH312 S F
CH3 CF3 CH3实施例 Q R1 R2 R3 R4 R5序号
熔点(℃)13 S F
H CF3 (CH2)3F nD 20=
1.543814 S F
CH3 CF3 (CH2)3F15 S F
H CH3 (CH2)3F16 S F
CH3 CH3 (CH2)3F17 O F
H CF3 CH3 14518 O F
H CF3 C2H519 O F
H CF3 CH3 115实施例
Q R1 R2 R3 R4 R5序号
熔点(℃)20 O F
H CF3 C2H521 O H
H CF3 CH322 O H
H CF3 CH323 O F
H CF3 CH3 15724 O F
H CF3 CH325 O F
H CF3 CH3 >20026 O F
H CF3 CH327 O F
H CF3 CH3实施例Q R1 R2 R3 R4 R5序号
熔点(℃)28 O F
H CF3 CH329 O F
H CF3 CH330 O F
H CF3 CH331 O F C2H5 H CF3 H 12332 O F C2H5 H CF3 CH3 12133 O F CH3 H CF3 C2H5 9034 O F
H CF3 H 18535 O F
H CF3 CH3 >200实施例
Q R1 R2 R3 R4 R5序号
熔点(℃)
6,33ppm(s,
1H)37 O F
H CF3 H 14038 O F
H CF3 H39 O F
H CF3 H 20240 O F C2H5 H CF3 CHF2 17741 O F
H CF3 H 20042 O F
H CF3 CH3实施例 Q R1 R2 R3 R4 R5序号
nD 20=1.562847 S F
CH3 CF3 CH348 O F
H CF3 H 88应用实施例实施例A苗前试验溶剂:5份重量丙酮乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量的活性化合物与所述量的溶剂混合,加入所述量的乳化剂,用水将乳油稀释到所需浓度。
将试验植物的种子播种到一般土壤中。24小时后对土壤施水或用活性化合物制剂喷雾。保持每单位面积水量一定是有好处的。制剂中活性化合物的浓度是不重要的,只有每单位面积施用的活性化合物的量是重要的。
三星期后,通过与未处理的对照物的生长相比较,以损伤百分率来表示对植物损伤的程度。数值的表示:
0%=没有作用(象未处理的对照物)
100%=完全损伤
在该项试验中,例如以8和125g/ha之间的施用比例、施用制备实施例2和4的化合物,显示出除杂草例如马唐属(90-100%),狗尾草属(95-100%),苘麻属(100%),黎属(100%)和母菊属(100%)的非常强的活性,并使农作物例如小麦有好的耐受性(0%)。实施例B苗后试验溶剂:5份重量丙酮乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量的活性化合物与所述量的溶剂混合,加入所述量的乳化剂,用水将乳油稀释到所需浓度。
用活性化合物制剂对高为5-15cm的试验植物喷雾,该方法是对每单位面积施用所需具体量的活性化合物。选择喷施液体的浓度,使按2000升水/公顷施用时,实际施用了具体所需量的活性化合物。
三星期后,通过与未处理的对照物的生长相比较,以损伤百分率来表示对植物损伤的程度。数值的表示:
0%=没有作用(象未处理的对照物)
100%=完全损伤
在该项试验中,例如以30和500g/ha之间的施用比例施用制备实施例2和4的化合物,显示出除杂草例如黍属(95-100%),狗尾草属(90-100%),蜀黍属(80-95%),苘麻属(100%),黎属(100%)和母菊属(100%)的非常强的活性,并使农作物例如小麦有好的耐受性(0%)。实施例C猿叶甲幼虫试验溶剂:7份重量二甲基甲酰胺乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,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,用水将乳油稀释到所需浓度。
甘蓝叶(Brassica oleracea)通过浸入到所需浓度的活性化合物的制剂中来处理,并在叶子仍湿润时用辣根猿叶甲幼虫(Phaedonvochleariae)侵染。
所需一定时间后,测定损伤百分率。100%表示已经杀死了所有的甲虫幼虫;0%表示没有杀死一只甲虫幼虫。
在该项试验中,例如通过制备实施例4的化合物,以0.1%活性化合物浓度为例,在7天后,引起100%的杀伤率。实施例D蛾试验溶剂:7份重量二甲基甲酰胺乳化剂:1份重量烷基芳基聚乙二醇醚
为制备活性化合物的合适的制剂,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,用水将乳油稀释到所需浓度。
甘蓝叶(Brassica oleracea)通过浸入到所需浓度的活性化合物的制剂中来处理,并在叶子仍湿润时用甘蓝蛾(Plutella maculipennis)的蠋侵染。
所需一定时间后,测定损伤百分率。100%表示已经杀死了所有的蠋;0%表示没有杀死一只蠋。
在该项试验中,例如通过0.1%作为例子的活性化合物浓度,用制备实施例4的化合物,在7天后,引起100%的杀伤率。
Claims (9)
1.通式(I)的氰基苯基嘧啶
其中:Q代表O、S、SO或SO2,R1代表氢、氰或卤原子,R2代表氢,或者代表选自下组的各自可有可无地被取代的残基:烷基、链烯基、炔烃基、环烷基、环烷基烷基、芳基、芳基烷基、杂环基和杂环基烷基,R3代表氢、卤原子或者代表选自下组的各自可有可无地被取代的残基:烷基和烷氧基,R4代表可有可无地被取代的烷基,和R5代表氢,或者代表选自下组的各自可有可无地被取代的残基:烷基、烷氧基、链烯基和炔烃基,但是排除已知的化合物1-(4-氰基-2-氟-5-甲基硫基-苯基)-3,6-二氢-2,6-二氧-3-甲基-4-三氟甲基-1(2H)-嘧啶,1-(4-氰基-2-氟-5-甲氧基羰基甲基硫-苯基)-3,6-二氢-2,6-二氧-3-甲基-4-三氟甲基-1(2H)-嘧啶和1-〔4-氰基-2-氟-5-(1-乙氧基羰基-乙基硫)-苯基〕-3,6-二氢-2,6-二氧-3-甲基-4-三氟甲基-1(2H)-嘧啶。
2.权利要求1的通式(I)的氰基苯基尿嘧啶特征在于Q 代表O、S、SO或SO2,R1代表氢、氰基、氟或氯,R2代表氢,代表分别可有可无地被氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷氧基-、C1-C4-烷基-羰基-、C1-C4-烷氧基-羰基-、二(C1-C4-烷基)-氨基-羰基-或N-C1-C4-烷基-N-苯基-氨基-羰基-(其中苯基可有可无地被氟、氯、溴、氰基、硝基、甲基或甲氧基取代)取代的,各种情况下至多有10个碳原子的烷基、链烯基或炔烃基,代表分别可有可无地被氰基-、羧基-、氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基取代的、在环烷基部分有3-8个碳原子且可有可无地在烷基部分最多有4个碳原子的环烷基或环烷基烷基,代表分别可有可无地被氰基-、羧基-、硝基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-,或C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基硫基-、C1-C4-烷基亚磺酰基-、C1-C4-烷基磺酰基-、C1-C4-烷基羰基-或C1-C4-烷氧基-羰基-(各自可有可无地被氟和/或氯取代),或苯基-、苯氧基-或苯基硫-(各自可有可无地被氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代的、在芳基部分有6或10个碳原子和可有可无地在烷基部分至多有4个碳原子的芳基或芳基烷基,R2进一步代表各自可有可无地被氰基-、羧基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-或C1-C4-烷基-、C1-C4-烷氧基-、C1-C4-烷基硫基-、C1-C4-烷基亚磺酰基-、C1-C4-烷基磺酰基-、C1-C4-烷基羰基-或C1-C4-烷氧基羰基-(各基团可有可无地被氟和/或氯取代),或苯基-、苯氧基-或苯基硫基-(各基团可有可无地被氟、氯、溴、氰基、甲基、甲氧基、三氟甲基和/或三氟甲氧基取代)取代的呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、氧杂环丁烷基(oxetanyl)、thietanyl、噁唑基、异噁唑基、噻唑基、噁二唑基、噻二唑基、吡唑基、吡啶基、嘧啶基、三嗪基、吲哚基、喹啉基或喹喔啉基,R3代表氢、氟、氯、溴或代表各自可有可无地被氟-和/或氯取代的、每种情况下有1至4个碳原子的烷基或烷氧基,R4代表可有可无地被氟和/或氯-取代的、有1-4个碳原子的烷基,和R5代表氢或代表各自可有可无地被氟-、氯-或C1-C4-烷氧基取代的、各种情况下最多有6个碳原子的烷基、烷氧基、链烯基或炔烃基,但是排除化合物1-(4-氰基-2-氟-5-甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1-(4-氰基-2-氟-5-甲氧基羰基甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和1-〔4-氰基-2-氟-5-(1-乙氧基羰基-乙基硫)-苯基〕-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶。
3.权利要求1的通式(I)的氰基苯基尿嘧啶,特征在于Q代表O、S、SO或SO2,R1代表氢、氟或氯,R2代表氢,代表各自可有可无地被氰基-、羧基-、氟-、氯-、甲氧基-、乙氧基-、正-或异-丙氧基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或异-丙氧基羰基-、二甲基氨基羰基-或二乙基氨基羰基-取代的甲基、乙基、正-或异-丙基、正-、异-、仲-或叔丁基、正-、异-、仲-或叔戊基、丙烯基、丁烯基、戊烯基、丙炔基、丁炔基或戊炔基,R2进一步代表各自可有可无地被氰基-、羧基-、氟-、氯-、溴-、甲基-、乙基-、正-或异-丙基-、甲氧基-、乙氧基-、正-或异-丙氧基-、乙酰基-或丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或异-丙氧基羰基-取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,R2进一步代表各自可有可无地被氰基-、羧基-、硝基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正-或异-丙基-、正-、异-、仲-或叔丁基-、三氟甲基-、甲氧基-、乙氧基-、正-或异-丙氧基-、甲基硫基-、乙基硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或异-丙氧基羰基-取代的苯基、苄基或苯基乙基,或R2进一步代表各自可有可无地被氰基-、羧基-、氨基甲酰基-、硫代氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正-或异-丙基-、甲氧基-、乙氧基-、正-或异-丙氧基-、甲基硫基-、乙基硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正-或并-丙氧基羰基-或苯基-、苯氧基-或苯基硫基-取代的呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、氧杂环丁烷基(oxetanyl)、thietanyl、噁唑基、异噁唑基、噻唑基、噁二唑基、噻二唑基、吡唑基、吡啶基、嘧啶基、三嗪基、吲哚基、喹啉基或喹喔啉基,R3代表氢、氟、氯、溴或甲基,R4代表甲基、乙基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氯代二氟甲基、氟代二氯甲基、氯乙基、氟乙基、二氟乙基、二氯乙基、氯氟乙基、氯代二氟乙基、氟代二氯乙基、三氟乙基、四氟乙基、氯代三氰乙基或五氟乙基和R5代表氢或代表各自可有可无地被氟-、氯-、甲氧基-或乙氧基-取代的甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-或仲丁氧基、丙烯基、丁烯基、丙炔基或丁炔基,但是排除化合物1-(4-氰基-2-氟-5-甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,1-(4-氰基-2-氟-5-甲氧基羰基甲基硫-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和1-〔4-氰基-2-氟-5-(1-乙氧基羰基-乙基硫基)-苯基〕-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶。
4.通式(Ia)的氰基苯基尿嘧啶,特征在于Q、R1、R2、R3和R4各如权利要求1所定义。
6.除草剂和/或杀虫剂,特征在于含有权利要求1至3和5中的至少一种通式(I)的氰基苯基尿嘧啶。
7.控制不期望植物和/或昆虫的方法,特征在于使权利要求1至3和5的通式(I)的氰基苯基尿嘧啶作用于不期望的植物和/或昆虫和/或其生长地点。
8.权利要求1至3和5通式(I)的氰基苯基尿嘧啶控制不期望植物和/或昆虫的用途。
9.制备除草剂和/或杀虫剂的方法,特征在于将权利要求1至3和5的通式(I)的氰基苯基尿嘧啶与增充剂和/或表面活性剂混合。
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WO2012097578A1 (zh) * | 2011-01-21 | 2012-07-26 | 吉林紫鑫药物研究有限公司 | 一种健脾和胃的药物组合物及其制备方法 |
CN102203071B (zh) * | 2008-10-02 | 2014-07-30 | 韩国化学研究院 | 尿嘧啶系化合物及包括其的除草剂 |
CN107001288A (zh) * | 2014-09-12 | 2017-08-01 | 拜耳作物科学股份公司 | 作为害虫防治剂的具有c‑c‑连接的尿嘧啶的芳基硫醚和芳基亚砜衍生物 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102203071B (zh) * | 2008-10-02 | 2014-07-30 | 韩国化学研究院 | 尿嘧啶系化合物及包括其的除草剂 |
WO2012097578A1 (zh) * | 2011-01-21 | 2012-07-26 | 吉林紫鑫药物研究有限公司 | 一种健脾和胃的药物组合物及其制备方法 |
CN107001288A (zh) * | 2014-09-12 | 2017-08-01 | 拜耳作物科学股份公司 | 作为害虫防治剂的具有c‑c‑连接的尿嘧啶的芳基硫醚和芳基亚砜衍生物 |
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