CN1117748C - 2,6－双取代的吡啶和2,4－双取代的嘧啶除草剂 - Google Patents
2,6－双取代的吡啶和2,4－双取代的嘧啶除草剂 Download PDFInfo
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- CN1117748C CN1117748C CN97117398A CN97117398A CN1117748C CN 1117748 C CN1117748 C CN 1117748C CN 97117398 A CN97117398 A CN 97117398A CN 97117398 A CN97117398 A CN 97117398A CN 1117748 C CN1117748 C CN 1117748C
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- Prior art keywords
- trifluoromethyl
- methyl
- pyridine
- compound
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- -1 2, 6 -disubstituted pyridines Chemical class 0.000 title claims abstract description 30
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 49
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 49
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 43
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 37
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 47
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 38
- 239000000460 chlorine Substances 0.000 claims description 37
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 31
- 239000011737 fluorine Substances 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
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- 230000012010 growth Effects 0.000 claims description 2
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- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
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- 239000001257 hydrogen Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
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- 239000000706 filtrate Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
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- 238000001556 precipitation Methods 0.000 description 5
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
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- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
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- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- 229950011008 tetrachloroethylene Drugs 0.000 description 1
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- 239000011135 tin Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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Abstract
可用常规方法制得通式(I)衍生物：其中A为任意取代的芳基或五、六元含氮杂芳基等；m为0-5、n为0-2的整数；R1为氢、卤、任意取代的烷基、烯基、炔基、烷氧基等；R2为氢、卤、任意取代的烷基、烯基、炔基、烷氧基等；X为氧或硫；Z为氮或CH；条件是：如果A为1-甲基-3-三氟甲基-吡唑-5-基基团。n是0，X为氧且Z为CH，则R2 m不是氢或3-三氟甲基或2，4-二氯或2，4-二甲基。这类化合物尤其可用作除草剂。
Description
本发明涉及某些2，6-双取代的吡啶和2，4-双取代的嘧啶，它们的制备及其作为除草剂的应用。
吡啶、嘧啶及其衍生物在药学领域和农业(除草剂、杀真菌剂、杀螨剂、驱虫药、驱鸟剂)、以及用于聚合物和纺织工业的试剂、中间体和化学物品中具有许多用途。
例如，(分别在DE 40 29 654和JO 2131-480中)披露将2-芳基嘧啶和2-嘧啶基-6-芳基吡啶用作杀真菌剂。EP 263,958涉及除草剂2，6-二苯基吡啶；EP354,766和425,247分别描述了结构相关的2，4-二苯基嘧啶类化合物，它们也被说成是除草剂。另一个例子是2，6-二苯氧基吡啶，在EP 572,093中它被作为除草剂。在DE29 35 578中揭示4-苯氧基-2-吡唑-1-基嘧啶具有杀真菌活性。Huelsen(Diplomarbet，Konstanz 1993)描述了四种不同性质的2-(1-甲基-3-三氟甲基-吡唑-5-基氧基)-6-苯基吡啶，但没有披露生物活性。
业已惊奇地发现在同时具有一个芳基和一个芳氧基或杂芳氧基的相关的新吡啶和嘧啶衍生物中，存在着良好的除草活性。在杂草出现前和出现后这些化合物对阔叶和禾草种类杂草都显示出未曾预料的优良的活性和良好的作物选择性。
因此，本发明提供通式I的2，6-取代的吡啶和2，4-取代的嘧啶：
其中
A代表任意取代的芳基或任意取代的五元或六元含氮杂芳基或二氟苯并二氧基(benzodioxolyl)；
m代表0-5的整数；
n代表0-2的整数；
R1(或各个R1)分别代表氢原子、卤原子、任意取代的烷基、烯基、炔基、烷氧基、烷氧基烷基、二烷氧基烷基、烷氧基烷氧基、烷硫基、氨基、烷基氨基、二烷基氨基、烷氧基氨基或亚胺甲基氨基基团；
R2(或各个R2)分别代表氢原子、卤原子、任意取代的烷基、烯基、炔基、卤代烷基、卤代烷氧基、烷氧基、烷氧基烷基、烷氧基烷氧基、烷硫基、卤代烷硫基、或硝基、氰基、SF5或烷基磺酰基或烷基亚磺酰基；
X代表氧或硫原子；
Z代表氮原子或CH基团；
条件是：
(a)在Z为N时，A代表被卤代烷基、卤代烷氧基或卤代烷硫基中的至少一个所取代的吡啶基；或者
(b)在Z为CH时，m和n为1，R1是连接在4-位上的烷基、烷氧基或烷基氨基并且R2代表三氟甲基。
作为取代基或其它取代基的部分或在A定义中的芳基为任意取代的苯基或萘基。在A的定义中，五元或六元杂芳基包括任意取代的含有一个或多个氮和/或氧和/或硫原子(最好为1-3个氮原子)的五元或六元杂环。这些基团的例子有：吡唑基、咪唑基、三唑基、四唑基、吡啶基、吡嗪基、嘧啶基、哒嗪基、异噁唑基、异噻唑基和三嗪基。就A被定义为“芳基”而言，该芳基还包括由上述五元或六元杂环与苯环缩合组成的二环体系，并且该五元或六元杂环可依次缩合有另一个苯环。A的另一个较好的实例是下式二氟苯并二氧基：
一般来说，如果上述任何部分包括烷基、烯基或炔基，除非另有规定，这些基团可以是直链的或支链的并可含有1-12个，最好是1-4个碳原子。这些基团的例子有：甲基、乙基、丙基、乙烯基、烯丙基、异丙基、丁基、异丁基和叔丁基。卤代烷基、卤代烷氧基、烷硫基、卤代烷硫基或烷氧基中的烷基部分适合于具有1-4个碳原子，最好为1或2个碳原子。在烷氧基烷基、烷氧基烷氧基或二烷氧基烷基中的碳原子数可高达6个，最好高达4个，例如甲氧基甲基、甲氧基甲氧基、甲氧基乙基、乙氧基甲基、乙氧基乙氧基、二甲氧基甲基。
“卤”是指氟、氯、溴或碘原子，最好为氟、氯或溴。卤代烷基、卤代烷硫基和卤代烷氧基最好为单、二或三氟烷基、烷硫基和烷氧基，特别是三氟甲基、二氟甲氧基、-三氟甲硫基和三氟甲氧基。
当任何基团被指明为任意取代的时，则该任选存在的取代基可以是习惯上用于改进和/或发展农药化合物的任何取代基，特别是保持或增强本发明化合物除草活性的取代基，或者影响药效的持久性、土壤或植物的渗透性或这种除草化合物其它要求的性能的取代基。在分子的各个部位可存在一个或多个相同或不同的取代基。对于上面限定的含有任意取代的烷基的部分来说，所述烷基包括卤代烷基、烷氧基、烷硫基、卤代烷氧基、烷基氨基和二烷基氨基的烷基部分，这种取代基的具体例子包括苯基、卤原子、硝基、氰基、羟基、C1-4烷氧基、C1-4卤代烷氧基和C1-4烷氧基羰基。
对于上面限定的含有任意取代的芳基或杂芳基的部分来说，任选的取代基包括卤素、特别是氟、氯和溴原子和硝基、氰基、氨基、羟基、C1-4烷基、C1-4烷氧基、C1-4卤代烷基、C1-4卤代烷氧基、C1-4卤代烷硫基和卤代硫烷基(halosulfanyl)如SF5。使用1-5个取代基是合适的，最好使用1-2个取代基。典型的卤代烷基、卤代烷氧基和卤代烷硫基是三氟甲基、三氟甲氧基、二氟甲氧基和三氟甲硫基。
数字m最好为1-3的整数，n最好为1(此时R1不是氢)。
通式I的化合物是油状物、树胶状或主要为结晶的固体物质，可将它们用于农业或相关领域中，在杂草出现前或出现后使用以控制不合需求的植物，如看麦娘(Alopecurus myosuroides)、稗(Echinochloa crus-galli)、狗尾草(Setariaviridis)、猪殃殃(Galium aparine)、繁缕(Stellaria media)、阿拉伯婆婆纳(Veronica persica)、小野芝麻(Lamium purpureum)、田堇(Viola arvensis)、苘麻(Abutilon theophrasti)、园叶牵牛(Ipomoea purpurea)和反枝苋(Amaranthusretroflexus)。本发明通式I的化合物在宽的浓度区域具有高的除草活性，并可在农业中使用。
较好的化合物是其中的A代表被一个或多个选自卤原子、烷基、烷氧基、卤代烷基、卤代烷氧基和五卤代硫烷基的相同或不同的取代基取代的苯基、吡啶基或吡唑基。
最好的化合物是A带有一个取代基，该取代基位于A基团连接位置的间位。
当A被氯原子或三氟甲基间位取代，特别当A是2-氯吡啶-4-基，1-甲基-3-三氟甲基吡唑-5-基或3-三氟甲基苯基时，可获得良好的控制不合要求的植物生长的结果。
使用X代表氧原子的化合物可获得特别好的控制杂草的结果。使用Z代表氮原子的化合物可获得最好的结果。
下面通式IA、IB、IC代表本发明较好的实例：
在式IA中，A代表2-三氟甲基吡啶-4-基或2-二氟甲氧基吡啶-4-基，R1的含义同上；R2、R2’、和R2”分别代表氢原子、氟、氯、或溴原子，它们中的一个或两个还可以是三氟甲基、三氟甲氧基或氰基，R2”还可以是C1-C4烷基，特别是叔丁基。
在式IB中，X代表卤代烷基、卤代烷氧基或卤代烷硫基，最好是二氟甲氧基，R1指卤原子或烷基或烷氧基。
在式式IC中，R1指烷基、烷氧基或烷基氨基，A的含义同上。
本发明可例举出下列化合物：
6-乙基-2-(4’-三氟甲基苯基)-4-(2”-三氟甲基-吡啶-4”-基氧基)嘧啶
6-乙基-2-(4’-三氟甲基苯基)-4-(2”-(2，2，2-三氟乙基)-吡啶-4”-基氧基)嘧啶
6-甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲氧基-吡啶-4”-基氧基)嘧啶
6-乙基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲氧基-吡啶-4”-基氧基)嘧啶
6-甲氧基甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲氧基-吡啶-4”-基氧基)嘧啶
6-甲氧基甲基-2-(4’-三氟甲基苯基)-4-[2”-(2，2，2-三氟乙基)-吡啶-4”-基氧基]嘧啶
6-甲基-2-(4’-三氟甲基苯基)-4-[2”-(1，1，2，2-四氟乙基)-吡啶-4”-基氧基]嘧啶
5-甲基-2-(4’-三氟甲基苯基)-4-[2”-(1，1，2，2-四氟乙基)-吡啶-4”-基氧基]嘧啶
6-甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲硫基-吡啶-4”-基氧基)嘧啶
5-甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲硫基-吡啶-4”-基氧基)嘧啶
6-甲氧基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲硫基-吡啶-4”-基氧基)嘧啶
4-乙基-2-(4’-三氟甲基苯基)-6-(1”-甲基-3-三氟甲基吡唑-5-基氧基)吡啶
4-甲基-2-(4’-三氟甲基苯基)-6-(2”-二氟甲氧基-吡啶-4”-基氧基)吡啶
4-甲基-2-(4’-三氟甲基苯基)-6-(2”-三氟甲基-吡啶-4”-基氧基)吡啶
4-甲基-2-(4’-三氟甲基苯基)-6-(3”-三氟甲基苯氧基]吡啶
本发明化合物可使用常规方法制得。
制备通式I化合物的合适的方法包括使通式III化合物
与通式IV化合物
A-XM
(IV)
反应，其中Z、A、R1、R2、m、n和X与上面的定义相同。Hal代表卤原子；m代表金属原子。
卤原子Hal可以是任何卤原子，适宜的有氟、氯或溴原子。金属原子M可以是任何金属原子，较好使用碱金属原子，最好是钠和钾。
或者，最好在碱的存在下，可以使通式XV的化合物
其中A、R2和m如上所定义，与R1-H(如果R1是任意取代的烷氧基、烷氧基烷氧基、-烷硫基、氨基、烷基氨基、二烷基氨基或烷氧基氨基)反应，形成通式I的化合物。
烯丙基型或炔丙基型化合物I(其中R1是炔基或烯基)可以最好在过渡金属催化剂或碱的存在下通过R1-H或其有机金属衍生物的反应由化合物I(其中R1是卤原子，最好是氯或溴)制得。
化合物XV可以通过III(其中R1是Hal，Z是氮、Hal，R2和m如上所定义)与约2当量如上所述的IV(其中X指氧)反应制得。
在实践中，该反应可在促进或至少不影响反应的溶剂的存在或不存在下进行。较好的溶剂是极性的、非质子传递溶剂或质子传递溶剂，合适的溶剂有N，N-二甲基甲酰胺或二甲亚砜或环丁砜，或者是醚，如四氢呋喃或二噁烷，或者是醇，或者是水，或其混合物。该反应是在环境温度和反应混合物的回流温度之间的温度下，较好在升温下，最好在回流温度下进行的。
Z代表C-H基团并且n为0的通式III化合物可如下获得：由通式V的化合物(其中R2和m如上所定义)：
与醛(较好是甲醛)和二烷基胺(较好是二甲胺)根据Org.Synthesis Col.Vol.III，305f所述在溶剂中(合适的是醇，较好为乙醇)反应，获得通式VI化合物：
随后根据DBP 21 47 288(1971)使该化合物与铵盐(合适的是醋酸铵)和通式VII化合物(其中Y是烷氧基或NH2基团，最好是乙氧基)在溶剂(合适的醇，最好为乙醇)反应，生成通式VIII化合物：
接着在升温下理想的是回流温度使VIII与磷酰卤(Muller，E.，Chem.Ber.42，423(1909)；Katrizky et al.，J.Chem.Soc.，Perkin Trans.Prat 1，1980，2743-2754)，最好是磷酰溴或磷酰氯反应进行转化，生成通式III化合物。
或者，Z代表C-H基团的通式III化合物的较好制备方法包括任选地在过渡金属催化剂的存在下，以适当的摩尔比使通式IX的2，6-二卤吡啶(其中R1和n如上所定义，各个Hal1和Hal2分别代表卤原子)
与通式(X)的有机金属苯衍生物(其中R2和m如上所定义，M代表碱金属原子或硼、锡、镁、锌或铜)反应，
所述碱金属可以是任何碱金属，最好是锂，反应可在非质子传递的极性溶剂中，最好在醚中进行，(参见Cook and Wakefield J.Chem.Soc.，1969，2376)生成通式III化合物，或者在非极性溶剂或水中进行反应，例如可参见Ali，N.M.et al，Tetrahedron，1992，8117。
可用类似于Gungor，T，Marsais，F和Queguiner，G，J.Organometallic Chem.，1981，139-150所述的方法，进一步将Z是CH、Hal是氟、R1是氢、R2和m如上所定义的式III化合物转化成n＝1、Z是CH、Hal是氟、R2和m如上所定义并且R1是位于3位的甲硫基(或选自前面所述的可以以亲电子试剂的形式引入的另一个基团)的式III化合物。
Z代表氮原子的式III化合物的制备方法包括使通式XI的盐酸苯甲脒(其中R2和m如上所定义)
与式XII化合物或其盐(其中R1 1和R2 2分别如上所定义，O-烷基较好是甲氧基或乙氧基)反应，生成通式XIII的嘧啶酮(其中R1还可以是羟基)，
通式XI化合物是已知的，或者可以根据现有技术描述的方法，如描述在Tetrahedron，33，1675f(1979)和J.Org.Chem.，26，412f(1960)中的方法制得。
可在有机溶剂(合适的是醇，最好为乙醇)中，在碱，合适的是金属烷氧化物，最好是乙氧化钠的存在下根据Liebigs Ann.1980，1392f进行式XI和XII化合物的反应。
可基本根据Davies和Pigott在J.Chem.Soc.，1945，347中的描述，通过与磷酰卤、亚硫酰卤或光气，最好是磷酰氯、磷酰溴，最好无溶剂的存在下，在升温下的反应使式XIII化合物随后转化成式III化合物。
可使用现有技术中已知的，如Tullock C.W.等在J.Am.Chem.Soc.1960，5197或者Kiburis J.Klister J.在J.Chem.Soc Chem.Com.1969，381中所述的方法，由R1是氯或氨基的式III化合物制得R1＝F的上述式III化合物。
通式IV化合物是已知的或可用已知的方法制得。可分别对其进行制备和分离，或者可以就地进行制备。通常，使通式XIV的化合物(其中A和X如上所定义)
A-XH
(XIV)
与合适的金属碱，如金属碳酸盐或氢化物进行反应。较好的金属盐是钠盐或钾盐。
如有必要，可使用常规的技术对通式I的化合物进行分离和纯化。
本发明还提供通式I化合物作为除草剂的用途。另外，通过用本发明组合物或式I化合物处理不合要求的植物生长场所，本发明还提供一种在该场所抑制(combating)不合要求植物生长的方法。一种合适的操作是叶面喷射，该场所最好是作物区的植物，具体的作物可以是谷物，玉米、大豆、向日葵或棉花，还可向该土壤施用具有预防性(pre-emergence)除草作用的化合物。所使用的活性成分的剂量可为0.01-10kg/ha，最好为0.05-1kg/ha。
本发明还包括本发明除草组合物的制备方法，所述方法包括将式I化合物掺混入至少一种载体中。
较好的是本发明组合物中至少有两种载体，其中至少一种是表面活性剂。
本发明组合物中的载体可以是任何能与活性成分配制以有助于对要处理的场所(可以是植物、种子或土壤)进行施用、或有助于储存、运输或操作的物质。载体可以是固体或液体，包括通常是气态的但压缩成液态的物质，并可使用通常用于配制储存组合物的载体。本发明较好的组合物含有0.5-95重量％活性成分。
合适的固态载体包括天然或合成的粘土和硅酸盐，例如天然硅酸盐如硅藻土；硅酸镁如滑石粉；硅酸铝镁如硅镁土和蛭石；硅酸铝如高岭土、蒙脱土和云母；碳酸钙；硫酸钙；硫酸铵；水合二氧化硅和和合成的硅酸钙或硅酸铝；单质如碳或硫；天然和合成的树脂，如氧茚树脂、聚氯乙烯树脂和苯乙烯聚合物和共聚物；固态聚氯酚类；沥青；蜡；固态肥料如过硫酸钙。
合适的液态载体包括水；醇如异丙醇和甘醇；酮如丙酮、甲乙酮、甲基异丁基酮和环己酮；醚；芳族或芳脂族烃类如苯、甲苯和二甲苯；石油馏分如汽油和轻质矿物油；氯化烃类如四氯化碳，全氯乙烯和三氯乙烷。各种液体的混合物通常是合适的。
农用组合物通常以浓缩物的形式配制和运输，用户在随后的使用中对其进行稀释。存在有少量的表面活性剂载体有助于该稀释过程。因此本发明组合物中最好至少有一种载体是表面活性剂。例如，组合物可至少含有两种载体，其中至少一种是表面活性剂。
表面活性剂可以是乳化剂、分散剂或湿润剂；它可以是离子的或非离子的。合适的表面活性剂的离子包括多丙烯酸和木素磺酸的钠盐或钙盐；分子中至少含有12个碳原子的脂肪酸或脂肪胺或酰胺与环氧乙烷和/或环氧丙烷的缩合产物；甘油、山梨醇、蔗糖或五赤藓醇的脂肪酸酯；它们与环氧乙烷和/或环氧丙烷的缩合产物；脂肪醇或脂肪酚的缩合产物如对辛基苯酚或对辛基甲酚与环氧乙烷和/环氧丙烷的缩合产物；这些缩合产物的硫酸盐或磺酸盐；碱金属或碱土金属盐，最好是钠盐或分子中至少含有10个碳原子硫酸或磺酸酯，例如十二烷基硫酸钠，仲烷基硫酸钠，磺化蓖麻油的硫酸盐，以及烷芳基磺酸钠，如十二烷基苯磺酸盐；以及环氧乙烷聚合物和环氧乙烷和环氧丙烷的共聚物。
本发明除草组合物还可含有其它活性成分，如具有杀虫或杀真菌性能的化合物，或其它除草剂。
含有本发明化合物的制剂可有100g活性成分(式I化合物)、30g分散剂(disperging agent)、3g消泡剂、2g构造剂(structure agent)、50g防冻剂、0.5g杀生物剂和加至1000ml的水。使用前用水对其进行稀释，形成要求的活性成分的浓度。
下列实施例用于说明本发明。下列实施例制得的化合物结构再用NMR和质谱进行确认。实施例 实施例1 盐酸β-二甲基氨基苯丙酮
将苯乙酮(29.1ml，0.25mol)、仲甲醛(12.0g，0.40mol)和盐酸二甲胺(28.5g，0.35mol)悬浮在乙醇(50ml)中。加入0.5ml浓盐酸并将混合物加热回流4小时。随后加入200ml丙酮并使生成的透明溶液冷却至环境温度。过滤收集沉淀并在乙醇中结晶之，得到无色晶状的标题化合物(40.7g，76％理论产率)，m.p.158℃。实施例2-4
如实施例1所述制得通式VI的其它试样。详情列于表1。
表1实施例 R2 mp(℃) 产率％2 3-三氟甲基 157 633 2，4-二氯 136 514 2，4-二甲基 134 72实施例5 6-苯基-2-吡啶酮
缓慢地将2-氯乙酸乙酯(10.6ml，0.1mol)加至热(105℃)吡啶(8.9ml，0.11mol)中并将温度保持在100-110℃。将生成的棕色油状物溶解在乙醇(60ml)中，加入盐酸β-二甲基氨基苯丙酮(17.7g，0.1mol；由实施例1制得)和醋酸铵(60g)并使混合物沸腾回流4小时。冷却后，过滤混合物并在真空中蒸去溶剂。残余物在水中结晶，过滤收集晶体并在甲苯中重结晶纯化之。获得无色晶状标题化合物(4.7g，28％理论产率)，m.p.200℃。实施例6-8
用类似于实施例5的方法制得其它试样，详情列于表II。
表II- 实施例 R2 mp(℃) 产率％
6 3-三氟甲基 174 36
7 2，4-二氯 255 56
8 2，4-二甲基 209 23实施例9 2-溴-6-苯基吡啶
将6-苯基吡啶酮(3g，17.5mmol，由实施例6制得)和磷酰溴(7.2g，25.0mmol)的混合物在100℃加热5小时。将冷却后的混合物倒入水(40ml)中并加入碳酸氢纳饱和水溶液将pH调节至9。随后将各相分离，用50ml乙酸乙酯萃取水相。合并的有机相用无水硫酸镁干燥并在真空中蒸去溶剂。粗产物在乙醇水溶液中结晶。接着用闪蒸色谱(硅胶，己烷/乙酸乙酯体积比：9/1)纯化，得到2-溴-6-苯基吡啶浅棕色晶体(3.1g，76％理论产率)，m.p.50℃。实施例10-12
用相似于实施例9的方法制得通式III的其它化合物，详情列于表III
表III实施例 R2 mp(℃) 产率％10 3-三氟甲基 油状 8211 2，4-二氯 123 8812 2，4-二甲基 油状 68实施例13 2-(1’-甲基-3’-三氟甲基吡唑-5’-基氧基)-6-苯基吡啶
将2-溴-6-苯基吡啶(0.5g，2.1mmol；实施例9制得)、1-甲基-3-氟甲基-5-羟基吡唑(0.65g，3.9mmol)、碳酸钾(0.6g，4.3mmol)和N，N-二甲基甲酰胺(2ml)的混合物加热回流12小时。随后直接将反应混合物施加至闪蒸色谱柱(硅胶)上。用己烷/乙酸乙酯(9/1v/v)洗脱，得到浅黄色油状标题化合物(0.35g，52.0％理论产率)。实施例14-16
用相似于实施例13的方法制得表IV所列的化合物
表IV
实施例 A R2 mp(℃) 产率％14 1’-CH3-3’-CF3-吡唑-5’-基 3’-CF3 113 9315 1’-CH3-3’-CF3-吡唑-5’-基 2”，4”-二氯 91 7816 1’-CH3-3’-CF3-吡唑-5’-基 2”，4”-二甲基 油状 95实施例17 2-氟-6-(4’-氟苯基)-吡啶
在-20℃向1-溴-4-氟苯(34.3ml，0.31mol)在无水乙醚(200ml)中的溶液中加入丁基锂(105.0ml，0.26mol，2.5M的己烷溶液)。将混合物搅拌60分钟，随后冷却至-40 ℃。加入2，6-二氟吡啶(22.7ml，0.25mol)并将反应混合物温热至环境温度。接着，用氯化铵饱和水溶液(300ml)洗涤该混合物。进行相分离，水相用乙醚洗涤3次(每次100ml)。用无水硫酸镁干燥合并的有机相，在真空中除去溶剂，用闪蒸柱色谱法(硅胶，己烷/乙酸乙酯8/2)纯化粗产物，得到2-氟-6-(4’-氟苯基)-吡啶无色晶体(19.8g，41.0％理论产率)，m.p.34℃。实施例18-2-氟-6-(4’-氟苯基)-4-甲基吡啶
在氮气氛中将2-溴-6-氟-4-甲基吡啶(9.5g，50mmol)、4-氟苯硼酸(7.8g，56mmol)、碳酸氢钠(12.6g，150mmol)、水(200ml)和和催化量的四(三苯膦)合钯(O)在DME中的混合物加热回流过夜。将反应混合物过滤后，在减压下除去溶剂。使残余物在水和乙酸乙酯中进行分配。相分离并用乙酸乙酯洗涤水相。用无水硫酸镁干燥合并的有机相，在真空中除去溶剂。用闪蒸柱色谱法(硅胶，戊烷/乙酸乙酯9/1)纯化粗产物，得到2-氟-6-(4’-氟苯基)-4-甲基吡啶无色晶体(3.7g，36.1％理论产率)，m.p.49℃。实施例19 2-氟-6-)4’-三氟苯基〕-3-甲硫基吡啶
在-70℃向2-氟-6-(4’-氟苯基)吡啶(2.4g，10mmol，实施例17制得)在无水THF(35ml)中的溶液中滴加2M LDA在THF中的溶液(7.5ml，15mmol)。2小时后，在-70℃加入二甲二硫醚(disulfide)(1.41g，15mmol)并将反应混合物温热至-20℃。使反应混合物水解并用乙醚萃取之。分离后有机相用无水硫酸镁干燥。除去溶剂并用闪蒸色谱法(硅胶)纯化粗产物。用己烷/乙酸乙酯(20/1v/v)洗脱，得到标题化合物(1.2g，42％)。m.p.70-73℃。实施例20-23
用相似于实施例17的方法，制得列于表V的通式III的试样
表V实施例 R1 R2 mp(℃) 产率％20 - - 油状 4721 - 4’-三氟甲基 58 7522 - 3’-三氟甲基 油状 7223 - 3，4-二氟 油状 24实施例24-2-(3’-氯吡啶-5’-基氧基)-6-(4”-氟苯基氧基)吡啶
将2-氟-6-(4’-氟苯基)吡啶(1.9g，10.0mmol，实施例17制得)、3-氯-5-羟基吡啶(1.4g，11.0mmol)和碳酸钾(1.5g，11.0mmol)在环丁砜(10ml)中的混合物加热回流8小时。将混合物冷却至环境温度，随后用硅胶垫过滤之，并用乙酸乙酯洗涤该硅胶垫。合并有机溶液并在真空中除去溶剂。将残余的物质施加至闪蒸色谱柱(硅胶)的顶部并用己烷/乙酸乙酯洗脱。用己烷/乙酸乙酯(8/2v/v)洗脱得到2-(3’-氯吡啶-5’-基氧基)-6-(4”-氟苯基氧基)吡啶浅棕色晶体(1.4g，46％理论产率)。m.p.139℃。实施例25-43
用相似于实施例24的方法制得其它化合物，详情列于表VI
表VI
实施例 R1 A R2 mp(℃) 产率％25 - 3’-CF3-苯基 4”-氟 油状 4826 - 2’-氯吡啶-4’-基 4”-氟 137 3727 - 2’-氯吡啶-4’-基 - 109 3528 - 2’-氯吡啶-4’-基 4”-三氟甲基 105 5129 - 1’-CH3-3’-CF3-吡唑-5’-基 4”-氟 87 4430 - 1’-CH3-3’-CF3-吡唑-5’-基 4”-三氟甲基 94 5931 - 1’-CH3-3’-CF3-吡唑-5’-基 3”-三氟甲基 112 4432 - 2’-氯吡啶-4’-基 3”-三氟甲基 92 5433 - 2’，4’-二氟苯基 3”-三氟甲基 油状 7234 - 3’-CF3-苯基 4”-三氟甲基 油状 4435 4-CH3 1’-CH3-3’-CF3-吡唑-5’-基 4”-氟 85 4336 4-CH3 2’-氯吡啶-4’-基 4”-氟 115 3537 3-CH3S 3’-CF3-苯基 4”-三氟甲基 133-136 6738 3-CH3S 1’-CH3-3’-CF3-吡唑-5’-基 4”三氟甲基 154-156 4139 1’-CH3-3’-CF3-吡唑-5’-基 3”，4”-二氟 油状 29实施例40-盐酸4-氟苯甲脒
将4-氟苄腈(10g，83mmol)溶解在无水乙醇(5ml)和乙醚(70ml)的混合溶剂中。将反应混合物冷却至冰浴温度并用氯化氢气体鼓泡90分钟使之饱和。将混合物温热至环境温度并搅拌过夜。滤出无色沉淀，用乙醚洗涤后将其溶解在无水乙醇(20ml)中。加入氨气饱和的乙醚(100ml)并将溶液搅拌3小时。
过滤生成的悬浮液，在真空中除去滤液中的溶剂。残余物用二异丙醚洗涤。干燥后得到熔点为210℃的无色晶体(5.15g，35.5％)。实施例41-50
用与实施例40相同的方法制得通式XI的其它化合物。详情列于表VII。
表VII实施例 R2 mp(℃) 产率％41 4-三氟甲基 167 21.442 3-甲基 243 29.743 3-氯 148 17.544 3，4-二氟 185 17.445 3-三氟甲基 181 17.646 3-氟 143 20.047 4-溴 245 3948 4-氯 ＞250 8549 4-叔丁基 153 9250 4-三氟甲氧基 210 57实施例51 2-(4’-氟苯基)-5-甲基-4-嘧啶酮
在环境温度将氢化钠(0.52g，13mmol)加入20ml无水乙醇中并搅拌30分钟。向其中加入盐酸4-氟苯甲脒(1.47g，8.5mmol，实施例40制得)并将混合物再搅拌30分钟。滴加2-甲酰基丙酸甲酯(1g，10.6mmol)并在环境温度将反应混合物搅拌4天。
冷却后，在真空中除去溶剂，将残余物溶解在氢氧化钠水溶液(10ml，1M)中。随后用2M盐酸将混合物的pH调节至5。滤出沉淀，用二异丙醚洗涤之。干燥后，得到熔点＞250℃的无色晶体(0.44g，10.3％)。实施例52 6-羟基-2-(4’-三氟甲基苯基)-4-嘧啶酮
在甲醇钾(0.22mol)的无水乙醇(65ml)溶液中加入盐酸4-三氟甲基苯甲醚(22.4g，0.1mol，来自实施例41)，在环境温度下搅拌15分钟。加入二甲基丙二酸(12.6ml，0.11mol)，将混合物加热回流4小时。冷却后，用甲醇(50ml)稀释生成的悬浮液。
真空蒸发溶剂，将残留物溶解在水(50ml)中。然后用浓盐酸将混合物调节至pH1。滤出沉淀，用水洗涤。干燥后，获得浅黄色晶体(15.1g，59％)，其熔点＞200℃。实施例53 5-甲氧基-2-(4’-三氟甲基苯基)-4-嘧啶酮
在氢化钠(60％，6g，0.15mol)的无水THF(225ml)悬浮液中用30分钟加入甲氧基乙酸甲酯(14.9ml，0.15mol)的甲酸甲酯(11.1ml，0.18mol)溶液。在环境温度下搅拌混合物2小时。加入乙醚(300ml)后，通过抽滤可获得生成的甲氧基丙酸甲酯单醛钠盐。现在，将钠盐(0.075mol)加入盐酸4-三氟甲基苯甲醚(16.8g，0.075mol，来自实施例41)的无水乙醇(150ml)溶液中，环境温度下搅拌混合物48小时。加热回流1小时后，加入水(100ml)，然后过滤混合物溶液。
用乙酸将滤液调至pH5，真空蒸发乙醇。滤出沉淀用乙醇洗涤。干燥后，得晶体(13.7g，68％)，其熔点＞200℃。实施例54至78
利用实施例53中的方法，制备具有通式III的其它化合物。具体见表VIII。
表VIII 
实施例 R1 R2 mp(℃) 得率(％)54 6-甲基 4’-氟 267 56.855 5-甲基 4’-三氟甲基 ＞250 58.756 6-甲基 4’-三氟甲基 209 82.257 5-甲基 3’-甲基 169 34.358 6-甲基 3’-甲基 185 41.659 5-甲基 3’-氯 260 61.460 6-甲基 3’-氯 218 5161 5-甲基 3’，4’-二氟 ＞250 59.462 6-甲基 3’，4’-二氟 225 51.363 5-甲基 3’-三氟甲基 204 39.864 6-甲基 3’-三氟甲基 109 26.665 5，6-二甲基 3’-三氟甲基 215 70.466 5，6-二甲基 4’-三氟甲基 242 63.567 5-甲基 4’-氯 ＞250 27.268 6-甲基 4’-氯 227 6.869 5-甲基 3’-氟 238 5670 6-甲基 3’-氟 194 48.471 6-乙基 4’-三氟甲基 181 8772 5-甲基 4’-溴 ＞250 2073 6-甲基 4’-溴 245 3974 5-甲基 4’-叔丁基 218 8175 6-甲基 4’-叔丁基 213 7576 5，6-二甲基 4’-氯 276 4477 5，6-二甲基 4’-三氟甲氧基 228 7078 6-甲基 4’-三氟甲氧基 196 95实施例79-2-(4’-氟苯基)-4-氯-5-甲基嘧啶
将2-(4’-氟苯基)-5-甲基-4-嘧啶酮(0.79g，3.9mmol)(来自实施例55)和磷酰氯(3ml)的混合物加热回流1小时。
真空蒸发掉大部分的过量磷酰氯，用水(10ml)萃灭残留物以水解残留的反应试剂。中和混合物，然后用乙酸乙酯(50ml)萃取。用无水硫酸镁干燥有机层后，真空蒸发去除溶剂。得到无色晶体状标题化合物(0.63g，72.6％)，其熔点为133℃。实施例80 2-(4’-氯苯基)-4，5-二氯-6-甲氧基嘧啶
在2-(4’-氯苯基)-4，5，6-三氯嘧啶(1.85g，6.3mmol)的甲醇(30ml)和THF(60ML)溶液中加入钠(0.145g，6.3mmol)的甲醇(10ml)溶液，在环境温度下通宵搅拌混合物。真空蒸发溶剂后，在残留物中加入二氯甲烷，用水洗涤形成的混合物。用无水硫酸镁干燥有机层后，去除溶剂。用戊烷处理残留物，得无色晶体状标题化合物(1.75g，96％)，其熔点为157℃-159℃。实施例81-108
用实施例83的方法制备表IX中具有通式(XIII)的化合物。
表IX 实施例 R1 R2 mp(℃) 得率(％)81 6-甲基 4’-氟 143 9782 6-甲基 4’-三氟甲基 62 71.883 5-甲基 4’-三氟甲基 109 87.384 5-甲基 3’-甲基 154 98.885 6-甲基 3’-甲基 134 73.786 5-甲基 3’-氯 87 94.187 - 6-甲基 3’-氯 101 26.188 5-甲基 3’，4’-二氟 114 9289 6-甲基 3’，4’-二氟 94 90.790 5，6-二甲基 3’-三氟甲基 83 81.691 5，6-二甲基 4’-三氟甲基 57 54.592 5-甲基 3’-三氟甲基 101 81.493 6-甲基 3’-三氟甲基 62 87.394 5-甲基 4’-氯 162 85.295 6-甲基 4’-氯 101 83.696 5-甲基 3’-氟 95 83.797 6-甲基 3’-氟 86 71.598 6-乙基 4’-三氟甲基 35 8699 5-甲基 4’-溴 156-158 94100 6-甲基 4’-溴 110-112 94101 5-甲基 4’-叔丁基 103-105 98102 6-甲基 4’-叔丁基 70-72 99103 5，6-二甲基 4’-氯 87 71104 5，6-二甲基 4’-三氟甲氧基 76 81105 5-甲基 4’-三氟甲氧基 129 91106 6-甲基 4’-三氟甲氧基 64 94107 6-氯 4’-三氟甲基 80 33108 5-甲氧基 4’-三氟甲基 108 31实施例109 2-(4’-氟苯基)-4-(3”-三氟甲基苯氧基)-6-甲基嘧啶
将2-(4’-氟苯基)-4-氯-6-甲基吡啶(0.6g，2.7mmol)(来自实施例85)，α，α，α-3-羟基三氟甲苯(0.49g，3mmol)和碳酸钾(0.41g，3mmol)在N，N-二甲基甲酰胺(3ml)中形成的溶液加热回流2小时。
冷却后，加入乙酸乙酯(10ml)，以乙醇为洗液令悬浮液滤过硅胶床。真空蒸发滤液中的溶剂，滤液快速硅胶柱色谱纯化残留物，以7/2的己烷/乙酸乙酯洗脱。去除溶剂后得熔点为58℃的无色晶体(0.53g，56.4％)。实施例110-183
利用实施例109的方法制备通式I的其它化合物。具体见表X。
表X 
实施 R1 R2 A mp(℃) 得率例 (％)110 5-甲基 4’-氟 1”-CH3-3”-CF3-吡唑-5”-基 133 54.7111 6-甲基 4’-氟 1”-CH3-3”-CF3-吡唑-5”-基 123 21112 6-甲基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 98 39.5113 6-甲基 4’-CF3 3”-CF3-苯基 89 79.9114 5-甲基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 147 27.6115 5-甲基 4’-CF3 3”-CF3-苯基 95 97.6116 5-甲基 3’-CH3 1”-CH3-3”-CF3-吡唑-5”-基 121 74.9117 5-甲基 3’-CH3 3”-CF3-苯基 71 74.5118 6-甲基 3’-CH3 1”-CH3-3”-CF3-吡唑-5”-基 113 74.9119 6-甲基 3’-CH3 3”-CF3-苯基 60 73.2120 5-甲基 3’-氯 1”-CH3-3”-CF3-吡唑-5”-基 116 35.4121 5-甲基 3’-氯 3”-CF3-苯基 105 52.4122 6-甲基 3’-氯 1”-CH3-3”-CF3-吡唑-5”-基 96 27.1123 5-甲基 2’，4’-二氟 3”-CF3-苯基 68 40.4124 5-甲基 2’，4’-二氟 2”-氯吡啶-4”-基 146 58.8125 6-甲基 2’，4’-二氟 1”-CH3-3”-CF3-吡唑-5”-基 78 56.4126 6-甲基 2’，4’-二氟 3”-CF3-苯基 64 65.3127 6-甲基 2’，4’-二氟 2”-氯吡啶-4”-基 162 31.7128 5-甲基 4’-CF3 2”-氯吡啶-4”-基 99 44.1129 5，6-二甲基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 136 13.2130 5，6-二甲基 4’-CF3 3”-CF3-苯基 73 65.6131 5，6-二甲基 3’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 132 30.3132 5，6-二甲基 3’-CF3 3”-CF3-苯基 105 67.5133 6-甲基 4’-CF3 1”-CH3-3”-C2F5-吡唑-5”-基 128 41134 6-甲基 4’-CF3 2”，2”-二氟-1”，3”-苯并间二氧杂 86 85
环戊烯-4”-基135 6-乙基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 75 46136 6-乙基 4’-CF3 2”-氯吡啶-4”-基 97 41137 6-甲基 3’-CF3 4”-氟苯基 78 92138 6-乙基 4’-CF3 3”-CF3-苯基 65 38139 5-甲基 3’-CF3 4”-氟苯基 109-111 86140 5-甲基 4’-Br 3”-CF3-苯基 110 100141 6-甲基 4’-Br 3”-CF3-苯基 86-88 89142 5-甲基 4’-叔丁基 1”-CH3-3”-CF3-吡唑-5”-基 149-151 92143 6-甲基 4’-叔丁基 1”-CH3-3”-CF3-吡唑-5”-基 119-121 78144 5-甲基 4’-叔丁基 3”-CF3-苯基 123-124 91145 6-甲基 4’-叔丁基 3”-CF3-苯基 油状 99146 6-甲基 4’-Cl 3”-CF3-苯基 68 29147 5，6-二甲基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 142 49148 5，6-二甲基 4’-Cl 2”-氯吡啶-4”-基 150 36149 5，6-二甲基 4’-Cl 3”-CF3-苯基 102 66150 5-甲基 1”-CH3-3”-CF3-吡唑-5”-基 140-150 75151 5，6-二甲基 3’-F 1”-CH3-3”-CF3-吡唑-5”-基 117 70152 5-甲基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 141 58153 5-甲基 4’-Cl 2”-氯吡啶-4”-基 125 31154 5-甲基 4’-Cl 3”-CF3-苯基 101 52155 6-甲基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 99 37156 6-甲基 4’-Cl 2”-氯吡啶-4”-基 15 18157 5-甲基 3’，4’-二氟 2”-氯吡啶-4”-基 146 59158 6-甲基 3’，4’-二氟 1”-CH3-3”-CF3-吡唑-5”-基 78 56159 6-甲基 3’，4’-二氟 3”-CF3-苯基 64 65160 6-甲基 3’，4’-二氟 2”-氯吡啶-4”-基 162 32161 5-甲基 4’-CF3O 1”-CH3-3”-CH3-吡唑-5”-基 117-121 58162 6-甲基 4’-CF3O 1”-CH3-3”-CH3-吡唑-5”-基 102-104 46163 5-甲基 4’-CF3O 1”-CH3-3”-叔丁基-吡唑-5”-基 96-98 58164 6-甲基 4’-CF3O 1”-CH3-3”-叔丁基-吡唑-5”-基 88-89 78165 6-甲基 4’-CF3 1”-CH3-3”-叔丁基-吡唑-5”-基 87-90 83166 6-甲基 4’-CF3O 3”-CF3-苯基 52 73167 6-甲基 4’-CF3O 2”-氯吡啶-4”-基 72 32168 5-甲基 4’-CF3O 3”-CF3-苯基 83 80169 5-甲基 4’-CF3O 2”-氯吡啶-4”-基 82 43170 5，6-二甲基 4’-CF3O 3”-CF3-苯基 75 66171 5，6-二甲基 4’-CF3O 2”-氯吡啶-4”-基 107 54172 5-甲基 3’，4’-二氟 3”-CF3-苯基 68 40173 6-甲基 4’-CF3O 1”-CH3-3”-CF3-吡唑-5”-基 11 43174 5-甲基 4’-CF3O 1”-CH3-3”-CF3-吡唑-5”-基 98 67175 5，6-二甲基 4’-CF3O 1”-CH3-3”-CF3-吡唑-5”-基 128 45176 6-甲氧基甲基 4’-Cl 2”-氯吡啶-4”-基 89-91 100177 6-甲氧基甲基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 113-115 94178 6-甲氧基甲基 4’-Cl 3”-CF3-苯基 140-142 92179 5-甲氧基 4’-CF3 2”-氯吡啶-4”-基 96 92180 5-甲氧基 4’-CF3 3”-CF3-苯基 80 95181 5-氯-6-甲氧基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 173-176 95182 5-氯-6-甲氧基 4’-Cl 3”-CF3-苯基 95-98 100183 5-甲氧基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 80 180实施例184 4，6-二(2”-氯吡啶-4”-基氧基)-2-(4’-三氟甲基苯基)嘧啶
4，6-二氯-2-(4’-三氟甲基苯基)嘧啶(2.93g，10mmol)(来自实施例111)，2-氯-4-羟基吡啶(2.85g，22mmol)和碳酸钾(3.04g，22mmol)在N，N-二甲基甲酰胺(20ml)中的混合物在80℃加热1小时。
冷却后，真空蒸发溶剂，加入1/1的乙酸乙酯/己烷(10ml)，悬浮液经硅胶床过滤。得到的溶液用水洗涤3次。用无水硫酸镁干燥有机层后，去除溶剂，用快速硅胶柱色谱纯化残留物，用8/2的己烷/乙酸乙酯洗脱。去除溶剂后熔点为141℃的无色晶体(4.1g，86％)。实施例185-187
按照实施例184的方法，制备表XI中通式(XVa)的化合物。
表XI 
实施例 R2 A mp(℃) 得率(％)185 4’-三氟甲基 1”-CH3-3”-CF3-吡唑-5”-基 168 86186 4’-三氟甲基 3”-CF3-苯基 92 88187 4’-氯 1”-CH3-3”-CF3-吡唑-5”-基 156 93实施例188 6-甲氧基-4-(2”-氯吡啶-4”-基氧基)-2-(4’-三氟甲基苯基)嘧啶
4，6-二(2”-氯吡啶-4”-基氧)-2-(4’-三氟甲基苯基)嘧啶(2.0g，4.2mmol来自实施例184)溶解在无水甲醇(5ml)中，在此溶液中滴加甲醇钾(4.2mmol)的甲醇(1.2ml)溶液，将化合物加热回流30分钟。
真空蒸发溶剂，用快速硅胶柱色谱纯化残留物，用9/1的己烷/乙酸乙酯洗脱。去除溶剂后得熔点为128℃的无色晶体(1.0，62％)。实施例189 4，6-二溴-2-(4’-三氟甲基苯基)嘧啶
4，6-二羟基-2-(4’-三氟甲基苯基)嘧啶(5.12g，20mmol)和磷酰溴(10ml)的混合物在100℃加热3小时。将形成的热悬浮液加入冰中，可抽滤得到产物。干燥后，获得几乎无色的熔点为87℃的晶体(6.5g，86％)。实施例190-203
按照实施例188或109的方法制备通式I的化合物。具体见表XII。
表XII 
实施例 R1 R2 A mp(℃) 得率(％)190 6-甲氧基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 130 64191 6-甲氧基 4’-CF3 3”-CF3-苯基 94 94192 6-甲硫基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 127 55143 6-甲硫基 4’-CF3 2”-氯吡啶-4”-基 106 41194 6-二甲基氨基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 148 90195 6-乙基氨基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 102 23196 6-甲氧基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 144 80197 6-甲氧基氨基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 178 16198 6-二甲基氨基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 143 13199 6-氨基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 149 80200 6-甲基氨基 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 114 97201 6-溴 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 110 57202 6-氯 4’-Cl 1”-CH3-3”-CF3-吡唑-5”-基 122 26203 6-氯 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 113 69实施例204 6-乙烯基-4(1”-甲基-3”-三氟甲基吡唑-5”-基)-2-(4”-三氟甲基苯基)嘧啶
6-溴-4(1”-甲基-3”-三氟甲基吡唑-5”-基)-2-(4”-三氟甲基苯基)嘧啶(2g，4.3mmol，来自实施例201)，三丁基锡酸乙烯酯(1.4ml，4.7mmol)，四(三苯基膦)钯(O)(0.1g，0.09mmol)，甲苯(20ml)和3晶体2，6-二叔丁基-4-甲基苯酚的混合物加热回流90分钟。冷却后，加入氟化吡啶鎓在THF/吡啶(4ml)中形成的1.2N溶液和吡啶(2ml)。在环境温度下搅拌溶液17小时。在形成的混合物中加入乙酸乙酯(100ml)，溶液用水和饱和碳酸氢钠溶液洗涤2次。用无水硫酸镁干燥有机层后，去除溶剂，-用7/3己烷/乙酸乙酯洗脱的快速硅胶柱色谱纯化残留物。去除溶剂后得几乎无色的晶体(1.45g，82％)，熔点为112℃。实施例205-214
按照实施例24的方法制备其它化合物。具体见表XIII。
表XIII
实施例 R1 A R2 得率(％)205 3-乙基 3’-CF3苯基 4”-三氟甲基 72-75206 5-乙基 3’-CF3-苯基 4”-三氟甲基 44-46207 4-甲基 1’-CH3-3’-CF3-吡唑-5’-基 4”-三氟甲基 98208 4-甲基 3’-CF3-苯基 4”-三氟甲基 油状209 4-甲基 1’-CH3-3’-CF3-吡唑-5’-基 3”，5”-二氯 117210 4-甲基 1’-CH3-3’-CF3-吡唑-5’-基 3”，5”-二(三氯甲基) 126211 4-甲基 1’-CH3-3’-CF3-吡唑-5’-基 3”-氯-4”-氟 101212 4-甲基 1’-CH3-3’-CF3-吡唑-5’-基 3”，4”-二氯 97213 3-甲基 3’-CF3-苯基 4”-三氟甲基 71-73214 3-甲基 1’-CH3-3’-CF3-吡唑-5’-基 4”-三氟甲基 130-133实施例215-221
按照实施例188的方法，从2，4-二芳基氧基-6-芳基吡啶开始制备其它化合物。具体见表XIII。
表XIII
实施例 R1 A R2 得率(％)215 4-甲氧基 1’-CH3-3’-CF3-吡唑-5’-基 4”-三氟甲基 102216 4-甲基氨基 1’-CH3-3’-CF3-吡唑-5’-基 4”-三氟甲基 168217 4-甲氧基 3’-CF3-苯基 4”-三氟甲基 油状218 4-C2H5 1’-CH3-3’-CF3-吡唑-5’-基 4”-三氟甲基 61219 4-CH3 2’-二氟甲氧基吡啶-4’-基 4”-三氟甲基 76-79220 4-CH3 2’-三氟甲基吡啶-4’-基 4”-三氟甲基 112-115221 4-C2H5 2’-三氟甲基苯基 4”-三氟甲基 油状
按以下所示制备
2，4-二(1”-甲基-3”-三氟甲基吡唑-5”-基氧基)-6-(4’-三氟甲基 苯基)吡啶的方法来制备需要的2，4-二芳基氧基-6-芳基吡啶：
将4-硝基-2，6-二氯吡啶(3.9g，20mmol)，1-甲基-3-三氟甲基-5-羟基吡唑(7.3g，44mmol)和碳酸钾(6.7g，48mmol)在无水环丁砜中形成的混合物在110℃通宵加热。将反应混合物冷却至环境温度，用戊烷/乙酸乙酯(体积比为1/1)稀释，经硅胶床过滤。滤液用水洗涤10次，用无水硫酸镁干燥，真空蒸发溶剂。用戊烷/乙酸乙酯洗脱的快速硅胶柱色谱纯化残留物。得到2，4-二(1”-甲基-3-三氟甲基吡唑-5”-基氧基)-6-(4’-三氟甲基苯基)吡啶(4.3g，m.p.：105℃)。
在氮气下，加热回流氯化二(苄腈)钯(0.19g，0.5mmol)和1，4-二(二苯基膦)丁烷(0.2g，0.5mmol)在无水甲苯(10ml)中形成的混合物。2小时后，加入4-三氟甲基苯硼酸(1.2g，6.5mmol)，2，4-二(1”-甲基-3”-三氟甲基吡唑-5”-基氧基)-6-氯吡啶(2.2g，5mmol)，乙醇(2.5ml)和1M碳酸氢钠水溶液(5ml)，混合物在氮气下再加热回流2小时。用乙酸乙酯稀释反应混合物，经硅胶床过滤。用水洗涤滤液，用无水硫酸镁干燥，真空蒸发溶剂。残留物经戊烷/乙酸乙酯(体积比为8/2)洗脱的快速硅胶柱色谱纯化。得到标题化合物的无色晶体(2g，73％)，其熔点为133℃。实施例222-300
按照实施例113的方法制备其它通式I所示的化合物。详见表XIV。
表XIV 
实施例 R1 R2 A mp(℃)222 5-甲基 4’-CF3 4”-氯-嘧啶-6”-基 107223 6-甲硫基 4’-氯 1”-CH3-3”-CF3-吡唑-５”-基 131224 6-溴 4’-CF3 2”-氯-吡啶-4”-基 108225 6-溴 4’-CF3 3”-CF3-苯基 96226 6-(二甲基氨基)-亚甲基氨基 4’-氯 1”-CH3-3”-CF3-吡唑-5”-基 126227 6-乙炔基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 117228 6-甲氧基甲基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 114-116229 6-甲氧基甲基 4’-CF3 3”-CF3-4”-氟苯基 71-73230 6-甲氧基甲基 4’-CF3 2”-氯-吡啶-4”-基 100-102231 4，5-二氯 4’-氯 1”-CH3-3”-CF3-吡唑-5”-基 156-160132 6-甲基 4’-SO2CH3 1”-CH3-3”-CF3-吡唑-5”-基 132233 6-甲基 4’-SO2CH3 3”-CF3-苯基 162234 6-甲基 4’-SO2CH3 2”-氯-吡啶-4”-基 168235 4-氟 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 124236 6-乙基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 90237 6-乙基 4’-CF3 3”-CF3-苯基 77238 6-乙基 4’-CF3 2”-氯-吡啶-4”-基 97239 6-乙基 4’-CF3 4”-氯-嘧啶-6”-基 86240 6-乙基 4’-CF3 6-(2，2，2-三氟乙氧基)-嘧啶-4”-基 105241 6-乙基 4’-CF3 2”，6”-二氯-吡啶-4”-基 158242 6-乙基 4’-CF3 6”-氰基-吡啶-4”-基 130243 6-乙基 4’-CF3 3”-CF3-4”-氟苯基 62244 4-氯 4’-CF3 3”-CF3-苯基 89245 4-氯 4’-CF3 2”-氯-吡啶-4”-基 104246 4-氯 4’-CF3 1”-CH3-3”-C2H5-吡唑-5”-基 108247 6-甲基 4’-CF3 2”-二氟甲氧基-吡啶-4”-基 89-92248 4-甲基氨基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 167249 6-乙氧基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 162250 6-(2-氟乙氧基) 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 148251 6-(2，2，2-三氟乙氧基) 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 133252 6-烯丙基氧基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 127253 5，6-二乙氧基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 93254 6-甲氧基甲基 4’-CF3 3”-CF3-苯基 56-59255 6-氰基甲基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 127-130256 6-肼基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 187257 4-氟 4’-CF3 3”-CF3-苯基 油状258 4-氟 4’-CF3 2”-氯-吡啶-4”-基 136259 4-碘 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 108260 6-甲基 4’-CHCl2 1”-CH3-3”-CF3-吡唑-5”-基 116261 6-二氟甲氧基 4’-CF3 3”-CF3-苯基 92-95262 4-氯-5-甲基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 146263 4-氟-5-甲基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 150264 4-氟-5-甲基 4’-CF3 3”-CF3-苯基 69265 4-氟-5-甲基 4’-CF3 2”-氯-吡啶-4”-基 129266 6-甲基 4’-CF3 2”-三氟甲基吡啶-4”-基 105267 6-甲基 4’-CN 1”-CH3-3”-CF3-吡唑-5”-基 177268 5-氯 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 135-140269 6-甲基 4’-CF3 2”-(2，2，2-三氟乙氧基)吡啶-4”-基 104-106270 4-氯 4’-CF3 2”-二氟甲基吡啶-4”-基 101-104271 6-甲基 4’-CF3 3”-CN-苯基 138272 5-异丙基 4’-CF3 3”-CF3-苯基 66273 6-甲氧基 4’-CF3 2”-三氟甲基吡啶-4”-基 84274 5-甲基 4’-CF3 2”-三氟甲基吡啶-4”-基 109275 4-氯 4’-CF3 2”-三氟甲基吡啶-4”-基 97276 6-甲基 4’，5’-二(CF3) 1”-CH3-3”-CF3-吡唑-5”-基 132277 6-甲基 4’，5’-二(CF3) 3”-CF3-苯基 93278 6-甲基 4’，5’-二(CF3) 2”-氯吡啶-4”-基 128279 4-二氟甲氧基 4’-CF3 1”-CH3-3”-CF3-吡唑-5”-基 108-110280 6-甲氧基 4’-CF3 2”-二氟甲基吡啶-4”-基 88-91281 5-甲基 4’-CF3 2”-二氟甲基吡啶-4”-基 101-103282 4-氯 4’-CF3 2”-(2，2，2-三氟乙氧基)吡啶-4”-基 98-101283 6-甲氧基 4’-CF3 2”-(2，2，2-三氟乙氧基)吡啶-4”-基 91-94284 5-甲基 4’-CF3 2”-(2，2，2-三氟乙氧基)吡啶-4”-基 74-76285 5-甲基 4’-CF3 3”-CF3O-苯基 73286 6-甲基 4’-CF3 3”-CF3O-苯基 63287 5-甲基 4’-CF3 2”-氰基吡啶-4”-基 133288 5-甲基 4’-CF3 2”-五氟乙基吡啶-4”-基 134289 6-甲基 4’-CF3 2”-五氟乙基吡啶-4”-基 91290 6-甲氧基甲基 4’-CF3 2”-三氟甲基吡啶-4”-基 70291 6-甲氧基 4’-CF3 2”-五氟乙基吡啶-4”-基 100292 6-乙基 4’-CF3 2”-三氟甲基吡啶-4”-基 59293 6-乙基 4’-CF3 2”-(2，2，2-三氟乙氧基)吡啶-4”-基 86294 6-乙基 4’-CF3 2”-二氟甲氧基吡啶-4”-基 92295 6-甲氧基甲基 4’-CF3 2”-二氟甲氧基吡啶-4”-基 118296 6-甲氧基甲基 4’-CF3 2”-(2，2，2-三氟乙氧基)吡啶-4”-基 103297 6-甲基 4’-CF3 2”-(1，1，2，2-四氟乙基)吡啶-4”-基298 6-甲基 4’-CF3 2”-二氟甲硫基吡啶-4”-基 70-73299 5-甲基 4’-CF3 2”-二氟甲硫基吡啶-4”-基 80-95300 6-甲氧基 4’-CF3 2”-二氟甲硫基吡啶-4”-基 67-70实施例301 除草活性
为了评价化合物的除草活性，用以下植物对本发明化合物进行试验。TRZAS小麦HORVW大麦GOSHI陆地棉HELAN向日葵ORYSA稻GLXMA大豆BEAVA甜菜
ZEAMX-玉蜀黍
ALOMY看麦娘
AVEFA野燕麦
ECHCG锡兰稗
SETVI狗尾草
GALAP猪殃殃
STEME繁缕
CHEAL藜
VERPE阿拉伯婆婆纳
LAMPU小野芝麻
VIOAR Viola arvensis田堇
SIDSP Sida spinosa
AMBAR豚草
ABUTH苘麻
IPOPU园叶牵牛
SINAL欧白芥
AMARE反枝苋
试验可分为两类，出芽前和出芽后。出芽前试验为在刚播撒了上述植物的种子的土地上喷洒化合物的水性制剂。出芽后试验为用所示溶液喷洒上述植株的幼苗。
试验所用的土是制备好的园艺肥土。试验所用的配制剂是用试验化合物的丙酮溶液制备的，其中含油按重量计0.4％烷基苯基/环氧乙烷缩合表面活性剂，其商品名为TRITON X 155。丙酮溶液用水稀释，形成的制剂其剂量水平相当于每公顷(ha)1000g或300g活性物质，按体积计相当于每公顷400L。作为对照，在出芽前试验中使用未处理的播种后土地，在出芽后试验中使用未处理的但已出芽的土地。
在对叶和土地喷洒后20天(如果是实施例13-16化合物，则在喷洒后13天)，目测评价试验化合物的除草效果，并记录为0-9级。0级表示杂草生长情况与未处理的对照相同，9级表示杂草死亡。线性级数中每增加1个单位就表示效果水平增加约10％。星号表示该种植株在试验中没有经过处理。
试验结果见下表，其中，用前述实施例表示化合物。星号表示该种植株在试验中没有经过处理。
表XV出芽前和出芽后施用本发明化合物的效果
| 实施例 | 用量g/公顷 | 施用时间 | TRZAW | HORVW | GOSHI | HELAN | ORYSA | GLXMA | BEAVA | ZEAMX | ALOMY | AVEFA | ECHCG | SETVI | GALAP | STEME | CHEAL | VERPE | LAMPU | VIOAR | SIDSP | AMBAR | ABUTH | IPOPU | SINAL | AMARE |
| 13 | 1000 | 出芽前出芽后 | ** | ** | ** | ** | 02 | 05 | 48 | 24 | ** | 22 | 45 | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | 58 | ** |
| 14 | 1000 | 出芽前出芽后 | ** | ** | ** | ** | 34 | 46 | 99 | 96 | ** | 66 | 87 | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | 88 | ** |
| 15 | 1000 | 出芽前出芽后 | ** | ** | ** | ** | 02 | 26 | 89 | 25 | ** | 22 | 57 | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | 66 | ** |
| 16 | 1000 | 出芽前出芽后 | ** | ** | ** | ** | 00 | 02 | 27 | 04 | ** | 02 | 22 | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | 25 | ** |
| 24 | 300 | 出芽前出芽后 | 10 | 00 | 01 | 01 | ** | ** | ** | 01 | 00 | ** | ** | 00 | 00 | 00 | ** | 00 | ** | 00 | ** | ** | ** | 00 | ** | ** |
| 25 | 300 | 出芽前出芽后 | 00 | 00 | 01 | 02 | ** | ** | ** | 02 | 00 | ** | ** | 10 | 00 | 00 | ** | 01 | ** | 01 | ** | ** | ** | 01 | ** | ** |
| 26 | 300 | 出芽前出芽后 | 11 | 02 | ** | 13 | ** | ** | ** | 12 | ** | ** | ** | 00 | 22 | 04 | 00 | 04 | ** | ** | ** | ** | 04 | 01 | ** | 05 |
| 27 | 300 | 出芽前出芽后 | 02 | 02 | ** | 03 | ** | ** | ** | 03 | ** | ** | ** | 01 | 01 | 02 | 00 | 03 | ** | ** | ** | ** | 03 | 02 | ** | 04 |
| 28 | 300 | 出芽前出芽后 | 03 | 33 | 04 | 05 | ** | ** | ** | 34 | 55 | ** | 64 | 96 | 25 | 74 | ** | 96 | 8* | 86 | 46 | 45 | 44 | 24 | ** | 96 |
| 29 | 300 | 出芽前出芽后 | 04 | 13 | ** | 04 | ** | ** | ** | 03 | ** | ** | ** | 83 | 03 | 75 | 86 | 88 | ** | ** | ** | ** | 05 | 04 | ** | 97 |
| 30 | 300 | 出芽前出芽后 | 44 | 65 | 36 | 36 | ** | ** | ** | 44 | 96 | ** | 86 | 97 | 65 | 96 | ** | 96 | 9* | 87 | 88 | 85 | 66 | 66 | ** | 95 |
| 31 | 300 | 出芽前出芽后 | 13 | 45 | 28 | 05 | ** | 35 | ** | 18 | 87 | ** | 54 | 97 | 76 | 97 | ** | 99 | 97 | 88 | ** | ** | 88 | 56 | ** | 97 |
| 32 | 300 | 出芽前出芽后 | 12 | 02 | 05 | 04 | ** | 03 | ** | 03 | 33 | ** | 22 | 84 | 14 | 65 | ** | 89 | 35 | 87 | ** | ** | 34 | 15 | ** | 95 |
| 实施例 | 用量g/公顷 | 施用时间 | TRZAW | HORVW | GOSHI | HELAN | ORYSA | GLXMA | BEAVA | ZEAMX | ALOMY | AVEFA | ECHCG | SETVI | GALAP | STEME | CHEAL | VERPE | LAMPU | VIOAR | SIDSP | AMBAR | ABUTH | IPOPU | SINAL | AMARE |
| 33 | 300 | 出芽前出芽后 | 20 | 00 | 00 | 00 | ** | 20 | ** | 00 | 00 | ** | 00 | 02 | 00 | 00 | ** | 00 | 00 | 00 | ** | ** | 00 | 51 | ** | 00 |
| 34 | 300 | 出芽前出芽后 | 12 | 32 | 35 | ** | 32 | 17 | ** | 22 | 74 | ** | 84 | 85 | 26 | 86 | ** | 99 | 86 | 96 | ** | 85 | 36 | 56 | ** | 87 |
| 39 | 300 | 出芽前出芽后 | 11 | 32 | 04 | ** | ** | 03 | ** | 03 | 53 | ** | 42 | 97 | 25 | 95 | ** | 99 | 85 | 97 | ** | 33 | 33 | 35 | ** | 95 |
| 109 | 300 | 出芽前出芽后 | 00 | 00 | 02 | 00 | ** | ** | ** | 00 | 00 | ** | 00 | 01 | 00 | 00 | 60 | 07 | 00 | 00 | 01 | ** | 00 | 02 | ** | 61 |
| 110 | 300 | 出芽前出芽后 | 34 | 45 | 26 | 16 | ** | ** | ** | 24 | 87 | ** | 67 | 96 | 28 | 97 | ** | 99 | 97 | 98 | 96 | ** | 56 | 34 | ** | 96 |
| 111 | 300 | 出芽前出芽后 | 13 | 33 | 05 | 05 | ** | ** | ** | 04 | 84 | ** | ** | 96 | 56 | 98 | 89 | 99 | 88 | ** | 66 | ** | 56 | 34 | ** | 96 |
| 112 | 300 | 出芽前出芽后 | 34 | 55 | 68 | 38 | ** | 58 | ** | 45 | 97 | ** | 86 | 98 | 87 | 98 | ** | 99 | 98 | 89 | ** | ** | 88 | 97 | ** | 98 |
| 113 | 300 | 出芽前出芽后 | 34 | 65 | 68 | 28 | ** | 38 | ** | 35 | 96 | ** | 87 | 99 | 87 | 98 | ** | 99 | 88 | 88 | ** | ** | 98 | 98 | ** | 97 |
| 114 | 300 | 出芽前出芽后 | 44 | 55 | 88 | 36 | ** | 46 | ** | 36 | 88 | ** | 85 | 98 | 87 | 98 | ** | 99 | 88 | 88 | ** | ** | 98 | 98 | ** | 97 |
| 115 | 300 | 出芽前出芽后 | 44 | 76 | 89 | 38 | ** | 58 | ** | 46 | 87 | ** | 86 | 98 | 87 | 98 | ** | 98 | 98 | 88 | ** | ** | 98 | 98 | ** | 98 |
| 116 | 300 | 出芽前出芽后 | 02 | 33 | 04 | 04 | ** | 05 | ** | 03 | 63 | ** | 42 | 98 | 03 | 64 | ** | 99 | 87 | 75 | ** | ** | 24 | 45 | ** | 85 |
| 117 | 300 | 出芽前出芽后 | 03 | 23 | 04 | 04 | ** | 04 | ** | 24 | 74 | ** | 53 | 94 | 14 | 54 | ** | 99 | 65 | 87 | ** | ** | 44 | 45 | ** | 97 |
| 118 | 300 | 出芽前出芽后 | 00 | 02 | 04 | 04 | ** | 03 | ** | 02 | 33 | ** | 43 | 74 | 13 | 23 | ** | 89 | 34 | 75 | ** | ** | 12 | 24 | ** | 95 |
| 实施例 | 用量g/公顷 | 施用时间 | TRZAW | HORVW | GOSHI | HELAN | ORYSA | GLXMA | BEAVA | ZEAMX | ALOMY | AVEFA | ECHCG | SETVI | GALAP | STEME | CHEAL | VERPE | LAMPU | VIOAR | SIDSP | AMBAR | ABUTH | IPOPU | SINAL | AMARE |
| 119 | 300 | 出芽前出芽后 | 00 | 02 | 00 | 02 | ** | 01 | ** | 01 | 01 | ** | 10 | 01 | 02 | 02 | ** | 03 | 01 | 25 | ** | ** | 01 | 03 | ** | 04 |
| 120 | 300 | 出芽前出芽后 | 12 | 34 | 25 | 04 | ** | 05 | ** | 23 | 85 | ** | 64 | 95 | 66 | 94 | ** | 89 | 88 | 87 | ** | ** | 55 | 54 | ** | 95 |
| 121 | 300 | 出芽前出芽后 | 23 | 34 | 28 | 04 | ** | 15 | ** | 35 | 85 | ** | 76 | 97 | 36 | 85 | ** | 99 | 77 | 88 | ** | ** | 54 | 45 | ** | 96 |
| 122 | 300 | 出芽前出芽后 | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** | ** |
| 123 | 300 | 出芽前出芽后 | 01 | 01 | 02 | 03 | ** | 02 | ** | 01 | 01 | ** | 02 | 02 | 03 | 04 | ** | 25 | 23 | 45 | ** | ** | 02 | 06 | ** | 44 |
| 124 | 300 | 出芽前出芽后 | 14 | 34 | 26 | 15 | ** | 55 | ** | 55 | 55 | ** | 66 | 87 | 34 | 95 | ** | 99 | 86 | 98 | ** | ** | 76 | 97 | ** | 96 |
| 125 | 300 | 出芽前出芽后 | 34 | 45 | 35 | 25 | ** | 36 | ** | 55 | 85 | ** | 76 | 97 | 45 | 96 | ** | 99 | 96 | 98 | ** | ** | 95 | 77 | ** | 96 |
| 126 | 300 | 出芽前出芽后 | 02 | 02 | 05 | 04 | ** | 03 | ** | 03 | 33 | ** | 03 | 93 | 14 | 74 | ** | 89 | 45 | 88 | ** | ** | 24 | 36 | ** | 95 |
| 127 | 300 | 出芽前出芽后 | 00 | 01 | 14 | 03 | ** | 02 | ** | 22 | 23 | ** | 02 | 84 | 03 | 75 | ** | 76 | 34 | 88 | ** | ** | 24 | 46 | ** | 86 |
| 128 | 300 | 出芽前出芽后 | 45 | 55 | 76 | 25 | ** | 35 | ** | 56 | 86 | ** | 77 | 97 | 56 | 96 | ** | 99 | 96 | 98 | ** | ** | 96 | 98 | ** | 97 |
| 129 | 300 | 出芽前出芽后 | 32 | 34 | 57 | 45 | ** | 35 | ** | 33 | 85 | ** | 65 | 96 | 55 | 95 | ** | 99 | 96 | 98 | ** | ** | 96 | 99 | ** | 96 |
| 130 | 300 | 出芽前出芽后 | 22 | 54 | 36 | 25 | ** | 35 | ** | 34 | 75 | ** | 65 | 97 | 45 | 96 | ** | 98 | 66 | 98 | ** | ** | 75 | 69 | ** | 86 |
| 131 | 300 | 出芽前出芽后 | 01 | 01 | 23 | 24 | ** | 02 | ** | 21 | 12 | ** | 02 | 82 | 04 | 44 | ** | 77 | 04 | 87 | ** | ** | 04 | 55 | ** | 84 |
| 实施例 | 用量g/公顷 | 施用时间 | TRZAW | HORVW | GOSHI | HELAN | ORYSA | GLXMA | BEAVA | ZEAMX | ALOMY | AVEFA | ECHCG | SETVI | GALAP | STEME | CHEAL | VERPE | LAMPU | VIOAR | SIDSP | AMBAR | ABUTH | IPOPU | SINAL | AMARE |
| 132 | 300 | 出芽前出芽后 | 00 | 01 | 03 | 02 | ** | 32 | ** | 01 | 00 | ** | 01 | 32 | 03 | 03 | ** | 04 | 03 | 35 | ** | ** | 02 | 35 | ** | 55 |
| 133 | 400 | 出芽前出芽后 | 53 | 54 | ** | ** | 55 | 76 | ** | 44 | 88 | ** | ** | 98 | 79 | ** | ** | 98 | 98 | ** | ** | ** | 99 | 99 | ** | ** |
| 134 | 400 | 出芽前出芽后 | 32 | 43 | ** | ** | 32 | 46 | ** | 43 | 84 | ** | ** | 98 | 37 | ** | ** | 99 | 78 | ** | ** | ** | 69 | 49 | ** | ** |
| 135 | 300 | 出芽前出芽后 | 64 | 76 | ** | ** | 54 | 46 | ** | 33 | 87 | ** | 86 | 97 | 36 | 87 | *8 | 99 | 89 | ** | ** | ** | 87 | 99 | ** | ** |
| 136 | 300 | 出芽前出芽后 | 65 | 86 | ** | ** | 55 | 46 | ** | 44 | 86 | ** | 87 | 87 | 16 | 98 | *6 | 99 | 87 | ** | ** | ** | 68 | 98 | ** | ** |
| 137 | 300 | 出芽前出芽后 | 00 | 01 | ** | ** | 01 | 01 | ** | 00 | 01 | ** | 00 | 00 | 01 | 01 | 5* | 02 | 02 | ** | ** | ** | 01 | 02 | ** | ** |
| 138 | 300 | 出芽前出芽后 | 64 | 77 | ** | ** | 44 | 47 | ** | 33 | 86 | ** | 86 | 97 | 45 | 97 | *7 | 99 | 98 | ** | ** | ** | 77 | 98 | ** | ** |
| 139 | 300 | 出芽前出芽后 | 01 | 02 | ** | ** | 01 | 02 | ** | 00 | 01 | ** | 01 | 01 | 01 | 01 | *4 | 03 | 02 | ** | ** | ** | 02 | 04 | ** | ** |
| 140 | 300 | 出芽前出芽后 | 43 | 54 | 55 | ** | 35 | 25 | ** | 23 | 87 | ** | 84 | 88 | 47 | 96 | ** | 99 | 98 | 96 | ** | 86 | 48 | 69 | ** | 89 |
| 141 | 300 | 出芽前出芽后 | 12 | 43 | 29 | ** | 22 | 14 | ** | 23 | 74 | ** | 83 | 95 | 15 | 95 | ** | 98 | 87 | 86 | ** | 56 | 25 | 49 | ** | 59 |
| 142 | 300 | 出芽前出芽后 | 00 | 01 | 15 | ** | 00 | 14 | ** | 02 | 00 | ** | 11 | 51 | 12 | 43 | ** | 55 | 14 | 76 | ** | 05 | 03 | 15 | ** | 05 |
| 143 | 300 | 出芽前出芽后 | 01 | 12 | 48 | ** | 20 | 23 | ** | 23 | 61 | ** | 52 | 83 | 36 | 95 | ** | 98 | 85 | 96 | ** | 87 | 46 | 57 | ** | 88 |
| 144 | 300 | 出芽前出芽后 | 01 | 01 | 06 | ** | 00 | 23 | ** | 02 | 00 | ** | 01 | 31 | 04 | ** | ** | 46 | 43 | 45 | ** | 05 | 03 | 44 | ** | 36 |
| 实施例 | 用量g/公顷 | 施用时间 | TRZAW | HORVW | GOSHI | HELAN | ORYSA | GLXMA | BEAVA | ZEAMX | ALOMY | AVEFA | ECHCG | SETVI | GALAP | STEME | CHEAL | VERPE | LAMPU | VIOAR | SIDSP | AMBAR | ABUTH | IPOPU | SINAL | AMARE |
| 145 | 300 | 出芽前出芽后 | 01 | 02 | 28 | ** | 00 | 14 | ** | 13 | 21 | ** | 22 | 52 | 05 | 35 | ** | 67 | 35 | 66 | ** | 26 | 05 | 25 | ** | 58 |
| 146 | 300 | 出芽前出芽后 | 00 | 00 | 04 | 05 | ** | 11 | ** | 04 | 75 | ** | 34 | 89 | 04 | 86 | ** | 97 | 44 | 87 | ** | 44 | 33 | 14 | ** | 94 |
| 147 | 300 | 出芽前出芽后 | 00 | 10 | 04 | 05 | ** | 14 | ** | 01 | 54 | ** | 33 | 75 | 04 | 65 | ** | 96 | 34 | 75 | ** | 34 | 34 | 35 | ** | 94 |
| 148 | 300 | 出芽前出芽后 | 00 | 00 | 03 | 04 | ** | 02 | ** | 02 | 11 | ** | 01 | 23 | 04 | 03 | ** | 84 | 03 | 86 | ** | 03 | 12 | 04 | ** | 94 |
| 149 | 300 | 出芽前出芽后 | 00 | 00 | 30 | 04 | ** | 02 | ** | 02 | 00 | ** | 00 | 02 | 04 | 03 | ** | 25 | 14 | 54 | ** | 04 | 01 | 04 | ** | 84 |
| 150 | 300 | 出芽前出芽后 | 22 | 44 | 46 | 25 | ** | 34 | ** | 44 | 86 | ** | 76 | 98 | 25 | 95 | ** | 97 | 97 | 97 | ** | 76 | 46 | 66 | ** | 97 |
| 151 | 300 | 出芽前出芽后 | 00 | 01 | 04 | 25 | ** | 03 | ** | 03 | 42 | ** | 02 | 04 | 04 | 65 | ** | 86 | 24 | 97 | ** | 44 | 12 | 14 | ** | 96 |
| 152 | 300 | 出芽前出芽后 | 32 | 44 | 56 | 46 | ** | 35 | ** | 45 | 88 | ** | 76 | 79 | 47 | 97 | ** | 97 | 87 | 97 | ** | 87 | 76 | 95 | ** | 87 |
| 153 | 300 | 出芽前出芽后 | 14 | 34 | 35 | 06 | ** | 14 | ** | 34 | 86 | ** | 75 | 78 | 15 | 96 | ** | 98 | 85 | 96 | ** | 44 | 55 | 55 | ** | 95 |
| 154 | 300 | 出芽前出芽后 | 45 | 56 | 4* | 2* | ** | 25 | ** | 47 | 8* | ** | 8* | 9* | 3* | 9* | ** | 9* | 9* | 9* | ** | 8* | 7* | 7* | ** | 9* |
| 155 | 300 | 出芽前出芽后 | 31 | 45 | 46 | 16 | ** | 15 | ** | 36 | 86 | ** | 87 | 98 | 46 | 97 | ** | 97 | 85 | 97 | ** | 85 | 86 | 65 | ** | 95 |
| 156 | 300 | 出芽前出芽后 | 20 | 21 | 04 | 05 | ** | *4 | ** | 04 | 65 | ** | 44 | 99 | 05 | 87 | ** | 97 | 44 | 96 | ** | 44 | 44 | 34 | ** | 95 |
| 157 | 300 | 出芽前出芽后 | 14 | 34 | 26 | 15 | ** | 55 | ** | 55 | 55 | ** | 66 | 87 | 34 | 95 | ** | 99 | 86 | 98 | ** | 75 | 76 | 97 | ** | 96 |
| 实施例 | 用量g/公顷 | 施用时间 | TRZAW | HORVW | GOSHI | HELAN | ORYSA | GLXMA | BEAVA | ZEAMX | ALOMY | AVEFA | ECHCG | SETVI | GALAP | STEME | CHEAL | VERPE | LAMPU | VIOAR | SIDSP | AMBAR | ABUTH | IPOPU | SINAL | AMARE |
| 158 | 300 | 出芽前出芽后 | 34 | 45 | 35 | 25 | ** | 36 | ** | 55 | 85 | ** | 76 | 97 | 45 | 96 | ** | 99 | 96 | 98 | ** | 75 | 95 | 77 | ** | 96 |
| 159 | 300 | 出芽前出芽后 | 02 | 02 | 05 | 04 | ** | 03 | ** | 03 | 33 | ** | 03 | 93 | 14 | 74 | ** | 89 | 45 | 88 | ** | 44 | 24 | 36 | ** | 95 |
| 160 | 300 | 出芽前出芽后 | 00 | 01 | 14 | 03 | ** | 02 | ** | 22 | 23 | ** | 02 | 84 | 03 | 75 | ** | 76 | 34 | 82 | ** | 25 | 24 | 46 | ** | 26 |
| 161 | 300 | 出芽前出芽后 | 00 | 01 | 03 | ** | 00 | 12 | ** | 00 | 00 | ** | 00 | 01 | 00 | 01 | ** | 11 | 01 | 05 | ** | 01 | 01 | 03 | ** | 02 |
| 162 | 300 | 出芽前出芽后 | 00 | 00 | 03 | ** | 00 | 02 | ** | 00 | 00 | ** | 00 | 00 | 01 | 01 | ** | 01 | 05 | 05 | ** | 00 | 00 | 02 | ** | 00 |
| 163 | 300 | 出芽前出芽后 | 01 | 01 | 05 | ** | 00 | 04 | ** | 02 | 00 | ** | 00 | 32 | 12 | 03 | ** | 36 | 04 | 25 | ** | 03 | 02 | 24 | ** | 05 |
| 164 | 300 | 出芽前出芽后 | 00 | 01 | 06 | ** | 20 | 04 | ** | 03 | 01 | ** | 01 | 51 | 02 | 64 | ** | 46 | 15 | 76 | ** | 13 | 03 | 15 | ** | 38 |
| 165 | 300 | 出芽前出芽后 | 02 | 33 | 59 | ** | 20 | 26 | ** | 23 | 83 | ** | 82 | 95 | 48 | 96 | ** | 99 | 97 | 96 | ** | 86 | 47 | 69 | ** | 88 |
| 166 | 300 | 出芽前出芽后 | 01 | 12 | 45 | ** | 22 | 17 | ** | 12 | 53 | ** | 73 | 54 | 26 | 55 | ** | 88 | 75 | 87 | ** | 64 | 26 | 45 | ** | 88 |
| 167 | 300 | 出芽前出芽后 | 22 | 33 | 56 | ** | 45 | 26 | ** | 33 | 86 | ** | 86 | 98 | 25 | 87 | ** | 98 | 86 | 86 | ** | 84 | 46 | 95 | ** | 88 |
| 168 | 300 | 出芽前出芽后 | 22 | 33 | 48 | ** | 02 | 37 | ** | 12 | 74 | ** | 54 | 85 | 15 | 55 | ** | 99 | 68 | 98 | ** | 56 | 45 | 38 | ** | 97 |
| 169 | 300 | 出芽前出芽后 | 33 | 33 | 59 | ** | 55 | 26 | ** | 33 | 85 | ** | 65 | 96 | 15 | 94 | ** | 98 | 87 | 97 | ** | 55 | 46 | 66 | ** | 97 |
| 170 | 300 | 出芽前出芽后 | 00 | 01 | 04 | ** | 00 | 05 | ** | 01 | 00 | ** | 00 | 20 | 02 | 01 | ** | 03 | 13 | 55 | ** | 03 | 02 | 24 | ** | 65 |
| 实施例 | 用量g/公顷 | 施用时间 | TRZAW | HORVW | GOSHI | HELAN | ORYSA | GLXMA | BEAVA | ZEAMX | ALOMY | AVEFA | ECHCG | SETVI | GALAP | STEME | CHEAL | VERPE | LAMPU | VIOAR | SIDSP | AMBAR | ABUTH | IPOPU | SINAL | AMARE |
| 171 | 300 | 出芽前出芽后 | 01 | 02 | 14 | ** | 00 | 04 | ** | 01 | 32 | ** | 22 | 63 | 04 | 02 | ** | 35 | 25 | 87 | ** | 04 | 04 | 14 | ** | 75 |
| 172 | 300 | 出芽前出芽后 | 01 | 01 | 02 | ** | ** | 02 | ** | 01 | 01 | ** | 02 | 02 | 03 | 04 | ** | 25 | 23 | 45 | ** | 12 | 02 | 06 | ** | 44 |
| 173 | 300 | 出芽前出芽后 | 12 | 33 | 66 | ** | ** | 27 | ** | 23 | 86 | ** | 86 | 97 | 66 | 87 | ** | 99 | 96 | 97 | ** | 86 | 56 | 88 | ** | 88 |
| 174 | 300 | 出芽前出芽后 | 32 | 33 | 56 | ** | 04 | 37 | ** | 23 | 85 | ** | 55 | 85 | 45 | 84 | ** | 99 | 87 | 98 | ** | 66 | 45 | 68 | ** | 97 |
| 175 | 300 | 出芽前出芽后 | 01 | 01 | 26 | ** | 0* | 17 | ** | 01 | 45 | ** | 15 | 75 | 05 | 25 | ** | 79 | 47 | 88 | ** | 16 | 05 | 08 | ** | 87 |
| 176 | 400 | 出芽前出芽后 | 33 | 24 | ** | ** | 22 | 32 | ** | 22 | 74 | ** | ** | 86 | 38 | ** | ** | 98 | 87 | ** | ** | ** | 28 | 89 | ** | ** |
| 177 | 400 | 出芽前出芽后 | 73 | 55 | ** | ** | 54 | 46 | ** | 44 | 86 | ** | ** | 97 | 57 | ** | ** | 99 | ** | ** | ** | ** | 67 | 96 | ** | ** |
| 178 | 400 | 出芽前出芽后 | 21 | 23 | ** | ** | 24 | 14 | ** | 13 | 63 | ** | ** | 84 | 45 | ** | ** | 89 | ** | ** | ** | ** | 25 | 34 | ** | ** |
| 188 | 400 | 出芽前出芽后 | 43 | 54 | ** | ** | 63 | 45 | ** | 53 | 97 | ** | ** | 98 | 89 | ** | ** | 99 | 98 | ** | ** | ** | 98 | 99 | ** | ** |
| 190 | 400 | 出芽前出芽后 | 54 | 65 | ** | ** | 54 | 57 | ** | 53 | 98 | ** | ** | 99 | 99 | ** | ** | 99 | 98 | ** | ** | ** | 99 | 99 | ** | ** |
| 191 | 400 | 出芽前出芽后 | 44 | 44 | ** | ** | 54 | 57 | ** | 43 | 98 | ** | ** | 98 | 89 | ** | ** | 99 | 98 | ** | ** | ** | 99 | 99 | ** | ** |
| 192 | 400 | 出芽前出芽后 | 43 | 44 | ** | ** | 33 | 56 | ** | 42 | 87 | ** | ** | 98 | 79 | ** | ** | 99 | 88 | ** | ** | ** | 99 | 99 | ** | ** |
| 193 | 400 | 出芽前出芽后 | 44 | 54 | ** | ** | 34 | 45 | ** | 43 | 88 | ** | ** | 99 | 78 | ** | ** | 98 | 87 | ** | ** | ** | 88 | 99 | ** | ** |
表XVI出芽前施用本发明化合物的效果
| 实施例 | 喷洒比[kg/ha] | G H O T ZL O R R EX R Y Z AM V S A MA W A W X | A A C G I L M S VB M A A P A A T EU B S L O M T E RT E O A H P I M PH L B P E U N E E | A D E SL I C EO G H TM S C VY A G I |
| 218 | 0.40.10.0250.0125 | 4 5 3 5 44 4 2 4 33 3 1 2 22 2 1 1 1 | 9 9 7 8 9 8 9 8 98 9 7 7 5 8 9 8 98 9 6 2 5 8 9 7 86 8 6 1 3 8 8 × × | 9 9 8 97 9 6 85 8 2 82 7 1 6 |
| 219 | 0.40.10.0250.0125 | 6 5 4 5 44 4 2 4 33 3 2 2 23 2 1 1 1 | 9 9 9 8 9 8 9 × 99 9 9 7 9 8 9 × 98 7 8 3 7 8 9 × 95 7 8 × 6 7 9 × 9 | 9 9 9 98 9 7 95 9 5 93 7 3 6 |
| 220 | 0.40.10.0250.0125 | 6 6 4 6 54 5 3 4 32 4 1 2 22 3 1 1 1 | 9 9 9 8 9 8 9 × 98 8 9 8 9 × 9 × 97 8 7 2 4 8 9 × 94 7 3 × 3 7 9 × 8 | 9 9 9 98 9 7 97 9 4 96 8 3 7 |
| 292 | 0.40.10.0250.0125 | 5 7 4 6 54 5 3 4 42 4 1 2 22 3 0 1 1 | 9 9 9 8 9 8 9 9 98 9 8 7 7 8 9 9 96 8 7 5 5 8 9 9 94 6 5 1 3 7 9 8 8 | 9 9 9 99 9 8 97 9 5 95 8 3 9 |
| 293 | 0.40.10.0250.0125 | 3 5 3 4 43 4 2 2 32 3 1 1 21 2 0 0 0 | 9 9 8 8 9 9 9 9 96 8 8 6 6 7 8 9 86 7 2 3 3 × 8 9 62 4 1 1 3 5 6 5 6 | 9 9 8 98 9 5 95 6 2 82 4 0 5 |
| 294 | 0.40.10.0250.0125 | 4 6 4 5 33 5 3 4 23 4 1 2 11 3 0 2 0 | 9 8 9 8 9 8 9 9 97 8 5 5 9 8 9 9 85 7 5 4 4 8 8 6 84 7 × 2 3 7 8 × 7 | 9 9 8 98 9 7 96 7 5 95 6 5 8 |
| 295 | 0.40.10.0250.0125 | 3 5 2 3 32 3 1 1 2× 2 0 0 10 1 0 0 0 | 6 9 8 6 6 8 9 8 84 8 2 4 5 7 9 8 8× 6 2 1 5 7 8 7 72 6 1 0 3 6 8 7 7 | 6 9 7 95 9 4 92 6 4 81 2 1 3 |
| 296 | 0.40.10.0250.0125 | 4 3 1 2 22 2 0 1 11 1 0 0 01 0 0 0 0 | 7 9 9 8 9 8 9 × 85 7 7 7 5 5 9 × 84 3 1 × 4 5 6 × 34 3 1 1 3 4 6 × × | 7 9 4 94 8 2 82 4 1 41 1 0 3 |
| 298 | 0.40.10.0250.0125 | 5 5 45 3 32 1 12 1 1 | 8 9 9 9 98 9 9 7 9× × 5 × ×5 7 5 5 8 | 9 8 97 8 9× 3 ×3 2 6 |
| 299 | 0.40.10.0250.0125 | 3 3 33 2 22 1 12 1 1 | 8 9 9 9 96 9 9 5 95 9 7 5 93 7 3 3 8 | 8 8 97 5 95 3 72 1 5 |
| 300 | 0.40.10.0250.0125 | 3 4 42 2 22 1 11 0 1 | 8 9 8 9 95 9 7 5 93 8 6 4 81 3 1 1 8 | 8 8 96 5 94 2 62 1 5 |
X表示无法进行评价。
表XVII
出芽后施用本发明化合物的效果
| 实施例 | 喷洒比[kg/ha] | G H O T ZL O R R EX R Y Z AM V S A MA W A W X | A A C G I L M S VB M A A P A A T EU B S L O M T E RT E O A H P I M PH L B P E U N E E | A D E SL I C EO G H TM S C VY A G I |
| 218 | 0.40.10.025 | 8 5 6 5 46 4 6 4 46 4 5 3 3 | 8 8 6 8 9 8 9 98 7 × 7 9 8 7 96 6 6 6 9 8 6 9 | 8 8 8 88 8 8 85 7 6 6 |
| 219 | 0.40.10.025 | 7 5 6 5 56 4 5 4 45 4 4 3 3 | 7 6 7 8 9 8 8 8 97 6 7 8 9 8 8 8 96 5 6 8 9 7 7 7 9 | 8 7 8 87 6 7 86 4 6 7 |
| 220 | 0.40.10.025 | 7 5 6 5 56 4 5 4 55 4 3 3 4 | 7 7 7 8 9 8 9 8 97 6 6 8 9 8 8 8 96 6 6 7 9 7 7 7 9 | 9 7 8 87 5 8 85 3 6 7 |
| 292 | 0.40.10.025 | 7 5 6 5 56 5 5 4 55 4 3 3 4 | 8 7 7 8 9 8 8 9 97 7 7 8 9 8 8 9 96 6 7 8 9 8 7 7 9 | 8 8 8 88 8 8 86 6 5 6 |
| 293 | 0.40.10.025 | 5 4 5 4 55 4 4 3 44 3 3 3 3 | 8 8 7 8 9 8 7 9 97 7 7 8 9 8 7 8 95 5 7 8 5 8 7 8 9 | 8 8 8 87 8 7 85 5 4 6 |
| 294 | 0.40.10.025 | 7 5 6 4 55 4 4 4 45 4 3 3 3 | 8 8 7 8 9 9 8 9 97 7 7 8 9 8 8 9 95 5 6 6 5 8 7 5 9 | 8 7 8 88 7 8 86 6 5 7 |
| 295 | 0.40.10.025 | 5 4 2 3 35 3 2 2 34 2 2 2 2 | 7 6 7 6 9 8 8 6 95 5 7 5 8 8 8 0 94 4 6 4 6 8 5 × 9 | 5 6 5 84 6 5 62 4 2 4 |
| 296 | 0.40.10.025 | 6 3 4 3 35 2 3 2 24 2 2 2 2 | 7 7 6 8 9 8 7 9 97 6 6 8 9 7 6 7 94 5 5 7 5 6 4 4 8 | 5 3 4 84 3 3 73 3 3 5 |
| 298 | 0.40.10.025 | 5 4 54 3 33 2 2 | 8 8 7 9 8× 7 7 9 86 6 5 9 7 | 9 98 97 9 |
| 299 | 0.40.10.025 | 6 4 34 3 23 2 2 | 9 8 7 9 88 7 7 9 75 4 7 9 7 | 9 97 95 9 |
| 300 | 0.40.10.025 | 4 4 34 3 22 2 2 | 9 8 7 9 88 7 7 9 85 4 6 9 7 | 9 98 96 8 |
Claims (11)
1.通式(I)的化合物：
其中
A代表取代的或未取代的苯基、吡唑基、吡啶基、嘧啶基或者二氟苯并二氧基，所述取代基选自卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基和C1-C4卤代烷硫基；
m代表1-2的整数；
n代表0-2的整数；
R1分别代表氢原子、卤原子、C1-C4烷基、氰基-C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4烯氧基、最多为6个碳原子的烷氧基烷基、C1-C4烷硫基、氨基、肼基、C1-C4烷基氨基、二(C1-C4烷基)氨基、C1-C4烷氧基氨基或二(C1-C4烷基)亚胺甲基氨基基团；
R2分别代表卤原子、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷基磺酰基、C1-C4卤代烷氧基；
X代表氧原子；
Z代表氮原子或CH基团；
条件是：
(a)在Z为N时，A代表被至少一个C1-C4卤代烷基、C1-C4卤代烷氧基或C1-C4卤代烷硫基所取代的吡啶基；或者
(b)在Z为CH时，m和n为1，R1是连接在4-位上的C1-C4烷基、C1-C4烷氧基或C1-C4烷基氨基并且R2代表三氟甲基。
2.如权利要求1所述的化合物，其特征在于A代表被一个或多个选自卤原子、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基的相同或不同的取代基取代的苯基、吡啶基或吡唑基。
3.如权利要求1所述的化合物，其特征在于它具有如下通式：
其中，A代表2-三氟甲基吡啶-4-基或2-二氟甲氧基吡啶-4-基，R1的含义同上；R2、R2’、和R2”分别代表氢原子、氟、氯或溴原子，它们中的一个或两个还可以是三氟甲基、三氟甲氧基或氰基，R2″还可以是C1-C4烷基。
4.如权利要求3所述的化合物，其特征在于所述R2″是叔丁基。
5.如权利要求1所述的化合物，其特征在于它选自：
其中，X代表C1-C4卤代烷基、C1-C4卤代烷氧基或C1-C4卤代烷硫基，R1指卤原子或C1-C4烷基或C1-C4烷氧基。
6.如权利要求1所述的化合物，其特征在于它选自：
6-甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲氧基-吡啶-4”-基氧基)嘧啶
6-乙基-2-(4’-三氟甲基苯基)-4-(2”-三氟甲基-吡啶-4”-基氧基)嘧啶
6-乙基-2-(4’-三氟甲基苯基)-4-(2”-(2，2，2-三氟乙基)-吡啶-4”-基氧基)嘧啶
6-乙基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲氧基-吡啶-4”-基氧基)嘧啶
6-甲氧基甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲氧基-吡啶-4”-基氧基)嘧啶
6-甲氧基甲基-2-(4’-三氟甲基苯基)-4-[2”-(2，2，2-三氟乙基)-吡啶-4”-基氧基]嘧啶
6-甲基-2-(4’-三氟甲基苯基)-4-[2”-(1，1，2，2-四氟乙基)-吡啶-4”-基氧基]嘧啶
5-甲基-2-(4’-三氟甲基苯基)-4-[2”-(1，1，2，2-四氟乙基)-吡啶-4”-基氧基]嘧啶
6-甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲硫基-吡啶-4”-基氧基)嘧啶
5-甲基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲硫基-吡啶-4”-基氧基)嘧啶
6-甲氧基-2-(4’-三氟甲基苯基)-4-(2”-二氟甲硫基-吡啶-4”-基氧基)嘧啶。
7..如权利要求1所述的化合物，其特征在于它具有如下通式：
其中R1是C1-C4烷基、C1-C4烷氧基或C1-C4烷基氨基，A的含义同前面任何一个权利要求中所述者。
8.如权利要求7所述的化合物，其特征在于它选自：
4-乙基-2-(4’-三氟甲基苯基)-6-(1”-甲基-3-三氟甲基吡唑-5-基氧基)吡啶
4-甲基-2-(4’-三氟甲基苯基)-6-(2”-二氟甲氧基-吡啶-4”-基氧基)吡啶
4-甲基-2-(4’-三氟甲基苯基)-6-(2”-三氟甲基-吡啶-4”-基氧基)吡啶
4-甲基-2-(4’-三氟甲基苯基)-6-(3”-三氟甲基苯氧基]吡啶。
9.一种除草组合物，包括至少一种如权利要求1-8中任何一项所述的化合物和载体和/或表面活性剂。
10.在植物生长场所抑制不需要的植物生长的方法，包括用有效量的至少一种如权利要求1-8中任何一项所述的化合物处理该场所。
11.使用有效量的如权利要求1-8中任何一项所述的化合物抑制不需要的植物的生长。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/693,422 US5849758A (en) | 1995-05-30 | 1996-08-07 | Herbicidal 2, 6-disubstituted pyridines and 2, 4-disubstituted pyrimidines |
| US08/693422 | 1996-08-07 | ||
| US08/693,422 | 1996-08-07 |
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| CN1175578A CN1175578A (zh) | 1998-03-11 |
| CN1117748C true CN1117748C (zh) | 2003-08-13 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN97117398A Expired - Fee Related CN1117748C (zh) | 1996-08-07 | 1997-08-07 | 2,6－双取代的吡啶和2,4－双取代的嘧啶除草剂 |
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| Country | Link |
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| US (1) | US5849758A (zh) |
| EP (1) | EP0823431A1 (zh) |
| JP (1) | JPH10114745A (zh) |
| KR (1) | KR19980018435A (zh) |
| CN (1) | CN1117748C (zh) |
| AR (1) | AR008281A1 (zh) |
| BR (1) | BR9704282A (zh) |
| CA (1) | CA2212310A1 (zh) |
| CZ (1) | CZ248197A3 (zh) |
| HU (1) | HUP9701361A3 (zh) |
| SG (1) | SG55357A1 (zh) |
| SK (1) | SK107797A3 (zh) |
| ZA (1) | ZA977009B (zh) |
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| CN1278607C (zh) | 1999-11-17 | 2006-10-11 | 拜尔公司 | 基于2,6－二取代的吡啶衍生物的选择性除草剂 |
| UA76708C2 (uk) * | 1999-12-08 | 2006-09-15 | Сінгента Патисипейшонс Аг | Антитіло, яке застосовується в імунологічному аналізі зразка для визначення неонікотиноїдного інсектициду, білковий кон'югат для одержання антитіла, спосіб визначення концентрації неонікотиноїдного інсектициду в зразку та набір для визначення кількості неонікотиноїдного інсектициду |
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| KR20020011986A (ko) * | 2000-03-16 | 2002-02-09 | 해피 페너 ; 해리 에이치. 페너 2세 | 5-치환된 아릴피리미딘 |
| ATE356812T1 (de) * | 2000-05-19 | 2007-04-15 | Basf Ag | Methode zur bekämpfung unerwünschten pflanzenwuchses in getreide |
| US6894003B2 (en) * | 2000-06-23 | 2005-05-17 | Basf Aktiengesellschaft | Enhancement of the activity of carotenoid biosynthesis inhibitor herbicides |
| CA2448198A1 (en) * | 2001-05-22 | 2002-12-05 | Neurogen Corporation | 5-substituted-2-arylpyridines as crf1 modulators |
| AR037233A1 (es) | 2001-09-07 | 2004-11-03 | Euro Celtique Sa | Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento |
| DE60305053T2 (de) * | 2002-08-19 | 2006-08-31 | Glaxo Group Ltd., Greenford | Pyrimidinderivate als selektive cox-2-inhibitoren |
| BR0314196A (pt) * | 2002-09-10 | 2005-07-26 | Scios Inc | Inibidores de tgf-beta |
| GB0221443D0 (en) * | 2002-09-16 | 2002-10-23 | Glaxo Group Ltd | Pyridine derivates |
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| CN111116565B (zh) * | 2020-04-01 | 2020-07-14 | 中科利健制药(广州)有限公司 | 2-芳基-4-（4-吡唑氧基）吡啶类化合物、其制备方法、药物组合物与应用 |
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| US3498984A (en) * | 1966-10-28 | 1970-03-03 | American Home Prod | 4-amino-2-phenyl-6-thiopyrimidines |
| US3940395A (en) * | 1969-08-29 | 1976-02-24 | American Home Products Corporation | 4-Amino-2-phenyl-6-thiopryimidines |
| DOP1981004033A (es) * | 1980-12-23 | 1990-12-29 | Ciba Geigy Ag | Procedimiento para proteger plantas de cultivo de la accion fitotoxica de herbicidas. |
| DE4029654A1 (de) * | 1990-09-19 | 1992-04-02 | Hoechst Ag | 2-phenyl-pyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| JPH05345780A (ja) * | 1991-12-24 | 1993-12-27 | Kumiai Chem Ind Co Ltd | ピリミジンまたはトリアジン誘導体及び除草剤 |
| TW231258B (zh) * | 1992-05-27 | 1994-10-01 | Shell Internat Res Schappej B V | |
| WO1996007633A1 (de) * | 1994-09-10 | 1996-03-14 | Basf Aktiengesellschaft | Phenylessigsäurealkylester |
-
1996
- 1996-08-07 US US08/693,422 patent/US5849758A/en not_active Expired - Fee Related
-
1997
- 1997-08-05 CA CA002212310A patent/CA2212310A1/en not_active Abandoned
- 1997-08-05 CZ CZ972481A patent/CZ248197A3/cs unknown
- 1997-08-06 KR KR1019970037543A patent/KR19980018435A/ko not_active Application Discontinuation
- 1997-08-06 HU HU9701361A patent/HUP9701361A3/hu unknown
- 1997-08-06 SG SG1997002807A patent/SG55357A1/en unknown
- 1997-08-06 AR ARP970103578A patent/AR008281A1/es unknown
- 1997-08-06 EP EP97305994A patent/EP0823431A1/en not_active Withdrawn
- 1997-08-06 ZA ZA977009A patent/ZA977009B/xx unknown
- 1997-08-06 BR BR9704282A patent/BR9704282A/pt not_active Application Discontinuation
- 1997-08-07 SK SK1077-97A patent/SK107797A3/sk unknown
- 1997-08-07 JP JP22443597A patent/JPH10114745A/ja not_active Withdrawn
- 1997-08-07 CN CN97117398A patent/CN1117748C/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994002470A1 (en) * | 1992-07-17 | 1994-02-03 | Shell Internationale Research Maatschappij B.V. | Pesticidal pyrimidine compounds |
| EP0723960A1 (en) * | 1995-01-26 | 1996-07-31 | American Cyanamid Company | Herbicidal 2,6-disubstituted pyridines and 2,4-disubstituted pyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1175578A (zh) | 1998-03-11 |
| ZA977009B (en) | 1999-02-08 |
| BR9704282A (pt) | 1998-12-29 |
| MX9706048A (es) | 1998-08-30 |
| JPH10114745A (ja) | 1998-05-06 |
| HU9701361D0 (en) | 1997-09-29 |
| EP0823431A1 (en) | 1998-02-11 |
| AR008281A1 (es) | 1999-12-29 |
| KR19980018435A (ko) | 1998-06-05 |
| HUP9701361A2 (hu) | 1998-06-29 |
| SG55357A1 (en) | 1998-12-21 |
| US5849758A (en) | 1998-12-15 |
| SK107797A3 (en) | 1998-08-05 |
| CZ248197A3 (cs) | 1998-06-17 |
| HUP9701361A3 (en) | 1999-03-01 |
| CA2212310A1 (en) | 1998-02-07 |
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