CN1035875C - 杀真菌的(2-芳基-2-取代的)乙基1，2，4-三唑 - Google Patents
杀真菌的(2-芳基-2-取代的)乙基1，2，4-三唑 Download PDFInfo
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- CN1035875C CN1035875C CN93107221A CN93107221A CN1035875C CN 1035875 C CN1035875 C CN 1035875C CN 93107221 A CN93107221 A CN 93107221A CN 93107221 A CN93107221 A CN 93107221A CN 1035875 C CN1035875 C CN 1035875C
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- Prior art keywords
- compound
- chlorophenyl
- triazol
- acid
- methyl
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims description 8
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- 150000003839 salts Chemical class 0.000 claims abstract description 36
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- 239000002184 metal Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 9
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- 150000001875 compounds Chemical class 0.000 claims description 57
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
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- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
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- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
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- IGJRKOFMYZEZRF-UHFFFAOYSA-M sodium 2-(dimethylamino)benzenesulfonate Chemical compound CN(C)C1=C(C=CC=C1)S(=O)(=O)[O-].[Na+] IGJRKOFMYZEZRF-UHFFFAOYSA-M 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229950004288 tosilate Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及一种新型的(2-芳基-2-取代的)乙基-1，2，4-三唑，它们的对映体，酸加成盐以及金属盐络合物，以及它们用作高活性的广谱内吸杀真菌剂。
Description
本发明涉及一种(2-芳基-2-取代的)乙基-1，2，4-三唑，其对映体，酸加成盐以及金属盐络合物，含有这些化合物的组合物，以及利用这些化合物作为杀真菌剂，特别是抵抗植物病原体的真菌。
美国专利4,366,165公开了1-和4-芳基氰基烷基-1，2，4-三唑作为杀真菌剂。该说明书的化合物限于那些具有一个连接在三唑上的烷基取代基的β碳原子上的氰基的化合物。
欧洲专利申请NO.61,798公开了2-乙基三唑衍生物，它在乙基的β碳原子上具有一个苯基取代基。该说明书中的所有化合物还具有一个氢原子，与β碳原子以及仲或叔氨基相连接。
欧洲专利申请NO.52,424公开了2-乙基取代的三唑化合物，其中乙基的β碳原子具有一个氯代，氰基，或氧代取代基。
英国专利申请GB2104065A公开了微生物的扁桃酸衍生物以及扁桃腈。这些化合物通常是2-乙基三唑，其中乙基的β碳原子被一个芳族取代基，一个氧代取代基，以及一个羧基或氰基所取代。该说明书的所有化合物要求乙基的β碳原子上的至少一个取代基是氧代取代基。
美国专利4,622,335公开了杀真菌的羟乙基吡咯基一肟衍生物。该说明书的化合物，除了在不对称碳上具有肟官能团之外，在同一碳上都具有羟基。
美国专利4,598,085公开了杀真菌的1-(2-芳基-2-R-乙基)-1H-1，2，4-三唑作为杀真菌剂。该说明书的化合物除了选择性取代的苯基以及低级烷基，环烷基，低级链烯基，芳基甲基以及芳基乙基取代基之外在乙基取代的三唑的β碳上都具有一个氢原子。
德国专利公开3408127公开了杀真菌的N-(吡咯基乙基)羧基酰胺。据报道该说明书的化合物具有一个羧基酰胺基，与三唑的乙基取代基的β碳相连接。
美国专利4,398,942公开了一种有除草活性的苯基乙腈。当这些化合物是取代的乙基三唑时，在乙基取代基的β碳上具有一个氰基或乙炔基。
本发明涉及一种新型的(2-芳基-2-取代的)乙基-1，2，4-三唑，其对映体，酸加成盐和金属盐络合物，以及它们作为高活性的广谱内吸杀真菌剂的应用。特别地，本发明涉及下式的化合物
其中X是-NC，-CH2N≡C，-CHO，-CON3，-CH＝NOR，-CH2NHCHO，-NHCO2R，-NHCONHR，-CH＝C(R)2，-NH2，-NHCHO，-NHCOCH3，-N＝C(R)2，-NCO，-NO2，或
；R独立地是氢，低级烷基，苯乙基，苯甲基，或苯基；Ar是选择性取代的芳基，Z是烷基，卤代烷基，环烷基，芳基，环烷基烷基或芳烷基；Q是1-(1，2，4-三唑基)或4-(1，2，4-三唑基)；以及它们的农学上可接受的对映体，酸加成盐以及金属盐络合物。
本发明涉及一种新型的(2-芳基-2-取代的)乙基-1，2，4-三唑，它们的对映体，酸加成盐和金属盐络合物，以及它们作为高活性的广谱内吸杀真菌剂的应用。特别地，本发明涉及下式的化合物其中Ar是选择性取代的芳基，例如苯基，萘基，吡啶基，噻吩基或呋喃基；
Z是(C2-C12)烷基，卤代烷基，环烷基，环烷基烷基，芳基或芳烷基；
Q是三唑基；以及
X是-NC，-CH2N≡C，-CHO，-CON3，-CH＝NOR，-CH2NHCHO，-NHCHO，-NHCOCH3，-NHCO2R，-NHCONHR，-NH2，-CH＝CR2，-N＝CR2，-OCO，-NH2，-CH＝CR2，-N＝CR2，-NCO，-NO2或
，其中R是氢或者低级烷基，以及它们的农学上可接受的对映体，酸加成盐以及金属盐络合物。
术语“烷基”包括碳原子为1-12的支链的或直链的烷基。典型的烷基是甲基，乙基，丙基，异丙基，正丁基，仲丁基，异一丁基，叔丁基，戊基，新戊基，异戊基，己基，庚基，异辛基，壬基，癸基，异癸基，十一基，十二基及其类似物。“低级烷基”指的是C1-C5烷基。
术语“卤代烷基”指的是被1至3个卤原子所取代的烷基。术语“烷氧基”指的是链长为1至12个碳原子的直链的或支链的烷氧基。术语“卤代烷氧基”指的是被1至3个卤原子所取代的烷氧基。术语“链烯基”指的是链长为2至12个碳原子和具有1至2个烯键的，直链或支链的，烯属不饱和的烃基。术语“卤代链烯基”指的是被1至3个卤原子所取代的链烯基。术语“炔基”指的是链长为2至12个碳原子和具有1至2个炔键的，直链或支链的炔基。术语“环烷基”指的是具有3至8个碳原子的饱和环体系。术语“环烯基”指的是具有5至8个碳原子，具有1至2个烯键的不饱和体系。术语“环烷基烷基”指的是被如上定义的低级烷基所取代的环烷基。
术语“芳基”指的是一种芳族环，选自苯基，萘基，吡啶基，噻吩基或呋喃基，优选的是一种苯基或萘基，其可被高达3个取代基选择性地取代，优选地被2个取代基选择性地取代，取代基选自卤原子，三卤甲基，苯基，苯氧基，选择性卤代的(C1～C4)烷基和(C1～C4)烷氧基。
典型的芳族取代基包括，但是不限于，苯基，萘基，4-氯代苯基，4-氟代苯基，4-溴代苯基，2-甲氧基苯基，2，4-二溴代苯基，3，5-二氟代苯基，2，4，6-三氯代苯基，2，3，4-三溴代苯基，3，4-二氯代苯基，2-氯-4-碘苯基，3，4，5-三甲基苯基，4-甲氧基苯基，2-氯代萘基，2，4-二甲氧基苯基，4-(三氟甲基)苯基，2，4-二碘代萘基，2-碘代-4-甲基苯基，2-，3-或4-吡啶基，2-或3-噻吩基，2-或3-呋喃基，及其类似物。
术语“芳烷基”定义为这样一种基团，其中烷基链是1至5个碳原子，可被支链化或直链化，优选的是后者，该基团的芳基部分如上所定义。典型的芳烷基取代基包括，但不限于2，4-二氯代苄基，2，4-二溴代苄基，2，4，6-三氯代苄基，3，5-二甲氧基苯乙基，2，4，5-三甲基苯丁基，2，4-二溴代萘基丁基，2，4-二氯代苯乙基，及其类似物。
在Q的定义中，术语“选择性取代的1-(1，2，4-三唑基)或4-(1，2，4-三唑基)”指的是包括未取代的1-和4-(1，2，4-三唑基)和1-和4-(1，2，4-三唑基)，它们可被选自卤原子或(C1～C4)烷基的两个取代基所取代。
本发明的一个优选实施例是式(I)的化合物，对映体，盐和络合物，其中Ar是苯基，或者被3个取代基，优选地被2个取代基所取代的苯基，取代基独立地选自卤原子，三卤代甲基，优选的是三氟代甲基，氰基，(C1-C4)烷基，(C1-C4)烷氧基，或苯基；Z选自(C2-C12)烷基，(C1-C12)卤代烷基，(C3-C8)环烷基，(C3-C8)环烷基(C1-C5)烷基，不饱和的苯基、苄基、或苯乙基，或者苯基，苄基或苯乙基，被两个卤原子或三卤代甲基所取代的芳族环；Q是未取代的1-(1，2，4-三唑)；以及R是H或(C1-C4)烷基。
本发明的一个更优选的实施例是式(I)的化合物，对映体，盐和络合物，其中Ar是苯基，或在4-位上被氯，溴，氟或三氟甲基所取代的苯基；Z是(C2-C6)烷基，苯基，苄基或苯乙基，或单个氯取代的苯基，苄基或苯乙基；Q是1-(1，2，4-三唑)；以及R是H。
本发明所包含的典型的化合物包括：N-{2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己基}甲酰胺；2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己基异氰化物；2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己醛；3-(4-氯代苯基)-3-〔(1，2，4-三唑-1-基)甲基〕-庚烯；2-(4-氯代苯基)-(E，Z)-1-羟基氨基-2-〔(12，4-三唑-1-基)甲基〕己醛；2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己酰叠氮化物；2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己胺；N-〔2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基〕甲酰胺；2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基异氰化物；以及N-〔2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基〕乙酰胺。
这里所述的化合物的合成采用三级串连合成，从芳基氰基乙基-1，2，4-三唑开始，其合成见属于Miller的美国专利4,366,165，该专利合并在此作为参考文献。
多级合成的步骤为本领域内的普通技术人员所熟知。例如，该合成可参见Jerry March所著Advanced OngaricChemistry Reactions Mechanism andStructure John Wiley and Sons，1985；下称“March”书。
属于Miller的美国专利4,366,165中的芳基氰基乙基-1，2，4-三唑的氰基，可以在强酸性条件下，水解成为相应的羧酸，例如采用浓盐酸，氢溴酸，或50％的硫酸，在大约100-140℃的温度下进行水解，见March书，P788。采用合适的还原剂，例如氢化铝锂，在合适的惰性溶剂中，在大约-20℃至10℃的温度下，这种酸又可被还原成为醇，见March书，P1099。另一种方法是，采用合适的还原剂，例如氢化铝锂，在合适的惰性溶剂中，例如乙醚或四氢呋喃中，氰基可以被还原成为胺，见March书，P815。
使用酸、醇和胺以获得本发明的新型的杀真菌剂。起始酸、醇和胺的制备的例子见下面的实施例A-D。
在一级步骤中，采用例如以铬为基的氧化剂，如三氧化铬/吡啶氯仿溶液，将2-取代的-2-芳基-2-〔(1，2，4-三唑-1-基)甲基〕-乙-1-醇氧化成为醛，见March书，P1057。醛又可用于获得三个进一步的衍生物：肟，肟醚(oxime ether)，以及烯烃(alkylene)。用盐酸羟胺或盐酸烷氧基胺来处理醛，可得到肟或肟醚，见March书P359和P805。向醛中加入来自溴化烷基(三苯基)磷鎓的内鎓盐(ylid)，在由快速色谱提纯之后，可得到一种烯烃，见March书，P845。用一种过酸，例如偏一氯代过苯甲酸来处理，烯烃可以被转化成为环氧化物，见March书，P735。烯烃也可被卤化，然后脱去卤化氢，以获得炔。
二级步骤从2-取代的-2-芳基-2-〔(1，2，4-三唑-1-基)甲基〕乙胺开始。将这种胺加入到混合的醛中，可得到次甲甲酰胺(methylenoformamide)，混合的醛是由乙酸酐与甲酸就地形成的。在室温下用3-乙基-2-氯苯并-噁唑鎓四氟硼酸盐(3-ethyl-α-chlorobenz-oxazolium tetrafluoroborate)使次甲甲酰胺脱水，在快速色谱之后，可得到亚甲基异氰化物，见March书，P934。
三级步骤从2-取代的-2-芳基-2-〔(1，2，4-三唑-1-基)甲基〕乙酸开始。用二苯基磷酰基叠氮化物和三乙胺处理，在室温下，经历大约15小时，得到羰基叠氮化物。在非醇溶剂中加热羰基叠氮化物，得到异氰酸盐，见March书，P984。当同样的反应在回流下进行48小时时，得到胺。用各种酰基氯或乙酸酐处理胺，可得到酰胺。胺也可以转化成为氨基甲酸酯或尿素。最后，用过酸氧化胺可得到硝基三唑。甲酰胺可脱水得到如上的异氰化物。
上述反应用下面的实例1-10来说明。本发明的另一个实施例包括下式的金属盐络合物
其中Ar，Z，Q和X如上述式(I)所定义，M是阳离子，选自周期表中的IIA，IB，IIB，IVA，VIB，VIIB，和VIII族，Y是一个阴离子相反离子，以这样一种方式选择Y，即使得阳离子M和阴离子Y的价电荷总数等于零。
本发明的金属盐络合物的典型的阳离子是镁，锰，铜，镍，锌铁，钴，钙，锡，镉，汞，铬，铅，钡及其类似物。
本发明所包括的典型的阴离子是氯化物，溴化物，碘化物，氟化物，硫酸盐，硫酸氢盐，高氯酸盐，硝酸盐，亚硝酸盐，磷酸盐，碳酸盐，碳酸氢盐，乙酸盐，柠檬酸盐，草酸盐，酒石酸盐，苹果酸盐，马来酸盐，富马酸盐，对甲苯磺酸盐，甲磺酸盐，单或二(C1～C4)烷基二硫代氨基甲酸盐，(C1-C4)亚烷基-双二硫代氨基甲酸盐，以及类似物。
制备本发明的酸加成盐时可使用的酸包括盐酸，氢溴酸，硝酸，硫酸，磷酸，氢碘酸，氢氟酸，高氯酸，对甲苯磺酸，甲磺酸，乙酸，柠檬酸，酒石酸，苹果酸，马来酸，草酸，富马酸，苯二甲酸及其类似物。
本发明的1，2 ，4-三唑的酸加成盐可以用本领域内公知的标准技术制备。例如，式(II)的1，2，4-三唑可以溶解在适宜的溶剂中，如二乙醚，四氢呋喃，乙醇，甲醇，及其类似物或它们的混合物中，并用等量的或过量的无机酸或有机酸进行处理，这些酸可以溶解或者可以不溶解在适宜的溶剂中。然后冷却或者蒸发混合物得到盐，盐可以直接使用，或者用适宜的溶剂或适宜溶剂的混合物重结晶。
上述1，2，4-三唑的金属盐络合物是这样制备的，即在搅拌下，滴加化学计量的溶解在适宜的溶剂或溶剂混合物中的金属盐。稍稍搅拌反应混合物，在减压下除去溶剂，得到式(II)的1，2，4-三唑金属盐络合物。
金属盐络合物也可以这样制备，即在喷洒植物之前，将化学计量的或过量的金属盐与式(I)的三唑，在所要求量的含有适宜的助剂的溶剂中混合。在该现场制备中可以包括的助剂是洗涤剂，乳化剂，润湿剂，铺展剂，分散剂，粘着剂，粘结剂，以及可以用在农业上的类似物。
在这些步骤中可以使用的溶剂包括极性溶剂，例如，水，甲醇乙醇，异丙醇或乙二醇，以及任何质子惰性的两极溶剂，例如，二甲基亚砜，乙腈，二甲基甲酰胺，硝基甲烷或丙酮。
在这些步骤中可用的金属盐阳离子可选自钙，镁，锰，铜，镍锌，铁，钴，锡，镉，汞，铬，铅，钡及其类似物。
任何适宜的阴离子，例如，氯化物，溴化物，碘化物，硫酸盐，硫酸氢盐，磷酸盐，硝酸盐，高氯酸盐，碳酸盐，碳酸氢盐，氢硫化物，氢氧化物，乙酸盐，草酸盐，苹果酸盐，柠檬酸盐以及类似物可用作金属盐中的相反离子。
本发明的化合物具有一个不对称的碳原子，并作为外消旋混合物存在。在这些外消旋混合物中，d和l对映体可经标准方法分离，例如用d-酒石酸，l-酒石酸，l-奎宁酸以及类似物分级结晶，接着碱化和萃取d或l对映体游离碱。
下面的实施例用于说明制备本发明的中间体和化合物的方法。实施例A2-4(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己酸
60.0g(0.208mol)的α-正-丁基-α-(4-氯代苯基)-1H-1，2，4-三唑-1-丙腈以及200ml的48％氢溴酸的混合物，在搅拌下回流加热96小时，之后，GLC表明不存在原料。用乙醚稀释反应，并用水萃取直至pH为中性。用足够的10％的氢氧化钠萃取乙醚，以保持pH为14，接着用35％的盐酸中和，此时形成白色固体沉淀。经过滤收集固体，并用水洗涤，直至漂洗水溶液为中性。产品在真空中干燥，得到49.0g的白色固体(产率为76.5％)，熔点为169-171℃。实施例B4-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕丁-1-醇
在1000ml的干四氢呋喃中的16g(0.42mol)的氢化铝锂的料浆，在N2中及在搅拌下，冷却至5℃，在1500ml的干四氢呋喃中的142g(0.40mol)的2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕丁酸被滴加，历经4小时，并保持温度在5-10℃。在室温下，将混合物搅拌16小时。在5℃下通过加入500ml饱和的硫酸钠中止反应，并在真空下除去溶剂。用甲苯过滤胶凝状固体，并用2×1000ml的水及1000ml的饱和的氯化钠溶液(盐水)洗涤。干燥溶剂，通过Celite_过滤，浓缩，得到99g的缓慢结晶的粘性的黄色玻璃体(产率为72.6％)，熔点为40-45℃。实施例C2-苯基-2-〔(1，2，4-三唑-1-基)甲基〕-1-己胺
向21g(0.55mol)的氢化铝锂中，在搅拌下，在N2中，加入在2500ml的干乙醚中的127g(0.50mol)的α-丁基-α-苯基-1H-1，2，4-三唑-1-丙腈，历经2.5小时。将反应再搅拌5小时，在此之后，GLC表明反应是完全的。用硫酸钠中止反应，过滤并分离有机相。用1000ml的乙醚萃取水相。合并有机相，用3×1.51的冰水洗涤，干燥，过滤并浓缩，不用外部加热，得到88g的浅绿色油状物(产率为69.2％)。实施例D4-(4-氯代苯基)-2-苯基-2-〔(1，2，4-三唑-1-基)甲基〕-1-丁胺
在搅拌下并在N2中，将在1000ml的干四氢呋喃中的18g(0.45mol)的氢化铝锂的料浆冷却至5℃。向料浆中加入在2000ml的干四氢呋喃中的α-(2-(4-氯代苯基)乙基)-α-苯基-1H-1，2，4-三唑-1-丙腈，历经3小时。在加入过程中，反应保持在5-10℃，然后使之温热至室温，并搅拌过夜。反应在冰浴中冷却，并通过缓慢加入硫酸钠中止反应。除去溶剂，并用乙酸乙酯萃取残留物，用1000ml的水和1000ml的盐水洗涤，干燥之后，除去溶剂，得到137g很粘的油状物(产率为89.5％)。实施例1N-(2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己基)甲酰胺
将1.09ml(11.51mmol)的乙酸酐和0.45ml(10.26mmol)的88％的甲酸的搅拌的混合物加热至50℃，在N2气下，历经2小时。将所得到的溶液冷却至0℃并加入在3ml的四氢呋喃中的1.0g(3.42mmol)的2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕-2-己胺。将该混合物温热至室温并搅拌24小时。该溶液倒入冰水中，并用乙醚萃取。用饱和的碳酸氢钠溶液洗涤合并的有机层，洗至用pH纸测试为碱性，然后用盐水洗涤，并用硫酸镁干燥。在减压下除去溶剂，得到1.0g的所要求的甲酰胺(产率为91％)，是一种糖浆的油状物(a syrupy oil)：1H-NMR(CDCl3，Me4Si)0.95(t，J＝6Hz，CH2-CH3)，1.0-1.5(m)，1.5-1.8(m)，3.0-3.75(m，CH2-NHCHO)，4.35(s，CH2-N)，7.1(m，aromatic H)，7.5(s，CH＝N)，7.7(s，CH＝N)，8.1ppm(brd，NHCHO)；IR(film)3300，3140，3060，2960，2940，1670，1500，1380，1275，1140，1010，960，830，680cm-1.实施例22-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己基异氰化物
在N2气下，向5ml的无水二氯甲烷中的0.50g(1.55mmol)的N-(2-(4-氯代苯基)-2-〔(1，2，4)-三唑-1-基)甲基〕己基)甲酰胺的搅拌溶液中，加入0.44ml(3.10mmol)的三乙胺，接着加入0.418g(1.55mmol)的3-乙基-2-氯代苯并噁唑鎓四氟硼酸盐。在室温下搅拌12小时后，将所得到的混合物倒入冰水中，并用乙酸乙酯萃取。合并的有机层用10％的盐酸，盐水各洗涤一次，并用硫酸镁干燥。在减压下除去溶剂，得到粗混合物，经色谱分离(Merck_60硅胶，50％乙酸乙酯-己烷)，得到0.300g的异氰化物(产率为64％)，是一种清澈，无色的油状物：1H-NMR(CDCl3，Me4Si)0.85(t，J＝6Hz，CH2-CH3)，1.0-1.55(m)，1.6-1.8(m)，3.4-4.0(m，CH2-NC)，4.55(d，J＝5Hz，CH2-triazole)，4.65(d，J＝12Hz，CH2-triazole，7.0-7.4(m，aromatic H)，7.85ppm(m，CH＝N)；IR(film)3140，3080，2960，2940，2880，2175，1610，1480，1470，1400，1270，1250，1140，1010，920，830，740，680cm-1.实施例32-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己醛
向10ml的二氯甲烷中的0.410g(4.1mmol)的三氧化铬的搅拌溶液中，加入0.65ml(8.2mmol)的吡啶。当所得到的混合物从黄色变为法国布尔戈尼红(burgundy)。(大约15分钟)后，加入0.200g(0.7mmol)的2-(4-氯代苯基)2-〔(1，2，4-三唑-1-基)甲基〕己-1-醇。30分钟之后，滗去上清液，残留物用乙醚洗涤两次。合并的有机层用5％的氢氧化钠洗三次，用5％的盐酸，5％的碳酸氢钠，盐水各洗两次，并用硫酸镁干燥。在减压下除去溶剂，得到浅黄色的油状物。在全真空下除去残余的吡啶，得到0.12g的醛(产率为63％)，是一种粘性的油状物：1H-NMR(CDCl3，Me4Si)0.9-1.1(t，J＝6Hz，CH2-CH3)，1.3-1.6(m)，1.8-2.3(m)，4.65s，CH2-N)，7.2(ABq，＝20.5Hz，JAB＝8Hz，phenyl H)，7.5(s，CH＝N)，7.8(s，CH＝N)，9.5ppm(s，CHO)；IR(film)3100，2940，2900，3840，1700，1575，1475，1260，1195，1125，1080，1000，820，745，665cm-1.实施例43-(4-氯代苯基)-3-〔(1，2，4-三唑-1-基)甲基〕-1-庚烯
向25ml的四氢呋喃中的1.64g(4.6mmol)的甲基三苯基磷鎓溴化物的搅拌溶液中，滴加3.0ml(4.2mmol)的1.4M正-丁基锂-己烷溶液。在2小时之后，加入在5ml的四氢呋喃中的1.22g(4.2mmol)的2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己醛，所得到的混合物回流加热48小时。加入冰中止反应，并用二氯甲烷分离产物，在减压下除去溶剂，经色谱分离(Marck_60硅胶，50％乙酸乙酯-己烷)，得到0.520g(产率为43％)的烯烃，是一种清澈，无色的油状物：1H-NMR(CDCl3，Me4Si)0.8-1.1(t，J＝6Hz，CH2-CH3)，1.2-1.7(m)，1.75-2.1(m)，4.6(s，CH2-N)，5.0-6.4(m，BH＝CH2)，7.1-7.3(m，phenyl H)，7.5(s，CH＝N)，7.9 ppm(s，CH＝N)；IR(film)3080，2950，2850，1650，1480，1450，1265，1130，1090，1010，950，920，830，680cm-1.实施例52-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己酰基叠氮化物
向3ml的二甲基甲酰胺的1.0g(3.25mmol)的2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己酸的搅拌溶液中，加入0.30ml的叔丁醇。该溶液冷至0℃，并加入1ml的二甲基甲酰胺中的1.07g(3.90mmol)的二苯基磷酰基叠氮化物，接着加入0.72ml(7.15mmol)的三乙胺。所得到的混合物搅拌2小时，然后温热至室温，再搅拌15小时。加入冰使产物沉淀。过滤得到1.10g的粗产物，它从乙酸乙酯和己烷的1∶3混合物中仔细地再结晶，得到0.46g(47％)的叠氮化物，是一种白色结晶性固体，熔点为100-101℃。1H-NMR(CDCl3，Me4Si)0.7-1.1(t，J＝6Hz，CH2-CH3)，1.1-1.7(m)，1.75-2.1(m)，4.6(d，CH2-N)，6.8-7.2(m，phenyl H)，7.3(s，CH＝N)，7.7 ppm(s，CH＝N)：13C-NMR(CDCl3)181.4，151，7，144.0，137.0，134.5 129.3，127.9，56.3，53.2，31，7，26.3，23.0，13.8ppm.IR3025，2975，2140，1695，1490，1270，1215，1180，1010，670cm-1.实施例62-(4-氯代苯基)-(E，Z)-1-羟基氨基-2-〔(12，4-三唑-1-基)甲基〕己醛
向4ml的乙醇中的1.20g(4.1mmol)的2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己醛的搅拌溶液中，加入0.360g(5.13mmol)的盐酸羟胺。将该混合物回流加热，加入1ml水中的0.27g(2.56mmol)的碳酸钠。再回流加热15小时之后，将混合物倒入被氯化钠所饱和的冰水中，并用乙酸乙酯萃取。用水，盐水各洗涤有机层一次，并用硫酸镁干燥。在减压下除去溶剂，得到1.1g(产率为87％)的肟，是一种白色固体，熔点为127-133℃。实施例72-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己胺
向10ml的叔丁醇中的1.0g(3.25mmol)的2-(4-氯代苯基)-2-〔(1，2 ，4-三唑-1-基)甲基〕己酸的搅拌溶液中，加入0.87ml(3.25mmol)的二苯基磷酰基叠氮化物，接着加入0.33ml的三乙胺。将该混合物回流加热48小时，在减压下除去叔丁醇，剩余物浸溶于5％的盐酸中，并用乙酸乙酯洗涤。用浓氢氧化铵使酸性水层成为碱性，并用乙酸乙酯萃取。从有机萃取物中除去溶剂，得到0.510g(产率为57％)的胺，是一种粘性的油状物。1H-NMR(CDCl3，Me4Si)0.8-1.2(t，J＝6Hz，CH2-CH3)，1.2-1.7(m)，1.7-2.2(m)，2.0(brs，-NH2)，4.6(s，CH2-N)，7.45(s，phenyl H)，7.8(s，CH＝N)，8.0ppm(s，CH＝N)；IR(film)3350，3260，2925，1650，1570，1470，1250，1180，1120，1070，990，810cm-1.实施例8N-〔2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基〕甲酰胺
在N2气中，将0.68ml(7.2mmol)的乙酸酐和0.28ml(6.42mmol)的88％的甲酸的混合物，加热至50℃，历经2小时。将所得到的溶液冷至0℃，并加入2ml的四氢呋喃中含有0.600g(2.14mmol)的2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己胺的溶液。使该混合物温热至室温，并搅拌48小时。将所得到的溶液倒入冰水中，并用乙酸乙酯萃取。水层用氯化钠饱和，并用乙酸乙酯萃取。合并的有机层用饱和的碳酸氢钠，盐水洗涤，并用硫酸镁干燥。在减压下除去溶剂，得到一种泡沫体。从乙酸乙酯-己烷中再结晶，得到0.35g(53％)的酰胺，它是一种白色的结晶性固体，熔点为129-131℃。1H-NMR(CDCl3，Me4Si)0.8(t，J＝6Hz，CH2-CH3)，1.0-1.5(m)，1.7-2.0(m)，4.95(brd，CH2-N)，7.3(m，phenyl H)，7.95(brs，CH＝N)，8.2(brd，-NCHO)，9.9ppm(brs，NHCHO)；IR3300，3150，3050，2980，2950，2880，1680，1490，1280，1140，1100，1015，840，680cm-1.实施例92-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基异氰化物
在N2气下，向5ml的二氯甲烷中含有0.40g(1.3mmol)的N-〔2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基〕甲酰胺的搅拌溶液中，加入0.45ml(3.26mmol)的三乙胺。向该混合物中加入0.439g(1.63mmol)的3-乙基-2-氯代苯并噁唑鎓四氟硼酸盐(在N2气下称重)于5ml的二氯甲烷中的料浆。然后使反应混合物在室温下搅拌12小时。将反应混合物倒入冰水，并用乙酸乙酯萃取。合并的有机层用10％的盐酸，盐水各洗涤一次，并用硫酸镁干燥。除去溶剂，得到一种粗油状物，它用柱色谱法提纯(Merck 60硅胶，乙酸乙酯/己烷)，得到0.20g(产率为52％)的清澈的，无色的油状物。1H-NMR 200MHz(CDCl3，Me4Si)0.8(t，J＝5Hz，CH2-CH3)，1.0-1.6(m，4H，1.90-2.2(m，2H)，4.55(ABq，J＝16.8Hz，JAB＝15Hz，CH2-N)，7.2-7.5(q，4H，aromatic H)，7.9(s，CH＝N)，8.0ppm(s，CH＝N).实施例10N-〔2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基〕乙酰胺
在N2中，向10ml的二氯甲烷中含有0.54g(1.94mmol)的〔2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己胺和0.02g(0.15mmol)的N，N-二甲基氨基吡啶的搅拌的，冷却的(0℃)溶液中，滴加0.50ml(5.28mmol)的乙酸酐。在5天之后，加入甲醇中止反应，除去溶剂得到一种白色的固体。将该固体溶于甲苯，在减压下除去甲苯以除去乙酸。所得到的固体从氯仿中再结晶，得到0.2g(32％)的白色晶体，熔点为178.5-179℃。1H-NMR 200MHz(CDCl3，Me4Si)0.85(t，J＝7.5Hz，CH2-CH3)，1.0-1.4(m，4H)，1.8-2.2(m，2H)，2.05(s，COCH3)，4.85(ABq，J＝35.3Hz，JAB＝12.5Hz，CH2-N)，5.95(s，NH)，7.05-7.4(q，aromatic H)，7.8(s，CH＝N)，7.95ppm(s，CH＝N).实施例11
试验本发明的实施例1-10的化合物对小麦白粉病(WPM)，小麦秆锈病(WSR)，稻瘟病(RB)，稻叶鞘亚麻枯萎病(RSB)，以及黄瓜霜霉病(CDM)的体内杀真菌活性。在对禾谷类的试验中(除了用于试验稻瘟病的稻株之外)，在施用杀真菌化合物之前的大约24小时修剪植株，以提供均一的植株高度，便于均匀施用该化合物和用真菌接种。该化合物溶解在水，丙酮和甲醇为2∶1∶1的混合物中，喷洒在植株上，使之干燥(4至6小时)，然后该植株用真菌接种。每个试验都使用对照的植株，它用水，丙酮和甲醇混合物喷洒，并用真菌接种。每个试验方法的其余部分在下面给出，结果载于表1中，以病毒控制的百分比来表示(用本发明的化合物处理的没有病害迹象的植株与未经处理的对照植株相比较)。
小麦白粉病(WPM)
在控制温度室(65°F至70°F)中，在Pennol小麦籽苗上培养麦类白粉病(Erysiphe graminis)(f.sp.tritici.从培养植株上摇下霉孢，置于Pennol小麦籽苗上，Pennol小麦籽苗已事先用杀真菌化合物喷洒过。经接种的籽苗保存在控制温度室(65°F至75°F)，并用地下水灌溉。在接种后8至10天评定病毒控制的百分比。
小麦秆锈病(WSR)
在Wanzer小麦籽苗上培养麦类秆锈病(Pucciniagraminis)(f.2p.tritici Racc 15B-2)，在温室中历经14天。得到来自感染植株的孢子水悬浮液，调节孢子的浓度为每ml去离子水有大约2×105孢子。通过施用秆锈病孢子悬浮液，使事先用杀真菌化合物处理过的Wanzer小麦籽苗被接种，直至用完，使用Devilbiss喷雾器，空气压力为每平方英寸51bs。接种之后，将植株放在接近75°F的湿环境中，置于12小时的连续的黑暗中，接着是最少3至4小时的光照，光强度为大约500呎烛光。室内的温度不超过85°F。在光照结束时，将植株置于温室中，使之生长两周，这时确定病害控制的百分比。
稻瘟病(RB)
用稻瘟病(Piricularia oryzae)(每ml大约20,000分生孢子)接种Nato稻株，用气刷将其喷洒在叶和茎上，直至观察到在叶子上形成了一层均匀的接种物膜。经接种的植株被培育在潮湿环境中(75°-85°F)，历经大约24小时，然后放在温室环境中(70°-75°F)。在接种后的7-8天，确定病害控制的百分比。
稻叶鞘亚麻枯萎病(RSB)
将Pellicularia filamentosa f.sp.sasiki培养在置于500ml锥烧瓶中的碎稻种和马铃薯葡萄糖液体培养基的高压锅蒸煮过的混合物上(每30ml的马铃薯葡萄糖液体培养基中有100g的稻种)。10天之后，在混合器中混合培养物以产生均匀的接种物。将近1茶匙的接种物撒在每盆(直径为3英寸)的土壤表面上的Lebonnet稻苗中。经接种的籽苗在湿室中(85°F-90°F)被培养5天。在从湿室中移出籽苗后，立即确定病害控制的百分比。
黄瓜霜霉病(CDM)
将黄瓜霜霉病(Pseudoperonospora Cubensis)保持在活的Marketeer黄瓜植株的叶子上，在恒定温度室(65°-75°F)中，在潮湿空气中，中等光强下放置7至8天。得到来自被感染的叶子上的孢子的水悬浮液，将孢子的浓度调节为每ml的水有大约1×105个孢子。用Devilbiss喷雾器喷洒叶子的下面，直至可以看到叶子上的小液滴，从而接种Marketeer黄瓜籽苗。经接种的植株在雾室中，在大约70°F下培养24小时，然后在一个控制温度的雾室(65°-75°F)中，继续培养6至7天。在接种后的7天，确定病害控制的百分比。
表1200ppm的1，2，4-三唑对各种真菌
的控制百分比％
| 实施例 | X WPM1 WSR2 RB3 RSB4 CDM5 |
| 1234568910 | -CH2NHCHO 80 0 0 0 0-CH2N≡C 80 100 0 0 0-CHO 100 100 70 50 0-CH＝CH2 100 100 80 60 80-CON3 100 70 -(6) 0 20-CH＝N-OH 100 100 0 0 0-NHCHO 100 60 0 - 0-N≡C 100 90 80 0 0-NHCOCH3 30 0 0 70 0 |
1小麦白粉病
2小麦秆锈病
3稻瘟病
4稻叶鞘亚麻枯萎病
5黄瓜霜霉病
6未试验
1，2，4-三唑，及其对映体，酸加成盐和金属盐络合物可用作农业上的杀真菌剂，并可用于各种场合，例如种子，土壤或叶片。为了这些目的，这些化合物可被制成专门的形式或纯形式使用，例如以溶液或者制剂形式使用。这些化合物通常溶解在载体中，或者这样配制，使得它们适合于以后用作杀真菌剂时的散布，例如，这些化学剂可以配制成可湿性粉末，乳油，粉剂，颗粒状制剂，气雾剂，或者可流动的乳油。在这样的制剂中，可在化合物中加入液体或固体载体，如果需要的话，可掺入合适的表面活性剂。
通常要求，特别在叶片喷洒制剂的情形下，包括辅助剂，例如润湿剂，铺展剂，分散剂，粘着剂，粘结剂以及适合于农业实践的类似物。本领域中常用的这样的辅助剂可参见John W.Mc Cutcheon，Inc.的出版物“Detergents andEmulsifiers，Annual”。
一般来说，本发明的化合物可以溶解在某种溶剂中，例如丙酮，甲醇，乙醇，二甲基-甲酰胺，吡啶或二甲基亚砜，并且这样的溶液可以用水稀释。溶液的浓度为大约1％至大约90％，优选的范围是大约5％至大约50％。
对制备乳油来说，化合物可以溶解在合适的有机溶剂，或溶剂的混合物中，连同一种乳化剂，它使得杀真菌剂分散在水中，在乳油中，活性成分的浓度通常是大约10％至大约90％，在可流动的乳油中，可以高达大约75％。
适用于喷洒的可湿性粉末可以这样制备，将本化合物与细碎的固体，例如粘土，无机硅酸盐和碳酸盐，和硅石相混合，并且在这样的混合物中掺入润湿剂，粘着剂，和/或分散剂。在这样的制剂中活性成分的浓度通常在大约20％至大约98％的范围内，优选的是大约40％至大约75％。一种典型的可湿性粉末是这样制备的，将50份的1，2，4-三唑，45份的合成的经沉淀的水合二氧化硅(出售商标为Hi-Sil_)，以及5份的木素磺酸钠混合。在另一个制备中，高岭土型(Barden)粘土用于取代上述的可湿性粉末中的Hi-Sil_，在另一个这样的制备中，25％的Hi-Sil_被合成的硅铝酸钠(出售商标为Zeolex_7)所取代。
粉剂是这样制备的，将1，2，4-三唑，或其对映体，盐和络合物与细碎的有机或无机惰性固体相混合。用于此目的的材料包括植物粉，二氧化硅，硅酸盐，碳酸盐和粘土。制备粉剂的一种常用的方法是用细碎的载体稀释可湿性粉末。含有大约20％至80％的有效成分的粉剂浓缩物是通常制备的，随后将其稀释为大约1％至大约10％的使用浓度。
1，2，4-三唑，及其对映体，盐和络合物作为杀真菌喷雾剂，可用常规方法施用，例如常用高加仑液压喷雾剂，低加仑喷雾剂，吹风喷雾剂，大气喷雾剂及粉剂。稀释度和施用率取决于所用设备的类型，施用的方法，欲处理的植株以及欲控制的病害。通常地，本发明的化合物的施用量是每英亩大约0.01磅至大约20磅的有效成分。
作为种子保护剂，涂敷在种子上的毒物的剂量通常为，每100磅的种子，大约0.05至大约20盎司，优选的是大约0.05至大约4盎司，更优选的是大约0.1至大约1盎司。作为土壤杀真菌剂，掺入土壤中的或施用在土壤表面的化学药品的量为每英亩大约0.02至大约20磅，优选的是大约0.05至大约10磅，更优选的是大约0.1至大约5磅。作为叶片杀真菌剂施用在生长的植株上的毒物的量为每英亩大约0.01至大约10磅，优选的是大约0.02至大约5磅，更优选的是大约0.25至大约1磅。
可与本发明的杀真菌剂结合使用的杀真菌剂包括：
(a)二硫代氨基甲酸盐及衍生物例如：福美铁，福美锌，代森锰，代森锰锌，代森锌，甲基代森锌，威百亩，福美双，代森锌和聚乙烯二硫化四烷基秋兰姆的络合物，棉隆，以及它们与铜盐的混合物。
(b)硝基苯酚衍生物，例如：敌螨普，乐杀螨，以及2-仲-丁基-4，6-二硝基苯基异丙基碳酸盐；
(c)杂环结构，例如克菌丹，灭菌丹，果绿宝，敌菌灵，ditalimfos，4-丁基-1，2，4-三唑，5-氨基-1-〔双(二甲基氨基)氧膦基〕-3-苯基-1，2，4-三唑，etradiazole，二噻农，克杀螨，苯菌灵，涕必灵，4-(2-氯代苯基亚膦基)-3-甲基-5-异噁唑酮，vinclozolin，iprodine，procymidone，氯苯氧基二甲乙基三唑乙醇，triadmefon，bitertanol，prochloraz，fenarimol，双-(对-氯代苯基)-3-吡啶甲醇，双-(对-氯代苯基)-5-嘧啶甲醇，triarimol，flutriafol，flusilazole，propiconazole，ectaconazole，myclobutanil，α-〔2-(4-氯代苯基)乙基〕-α-苯基-1H-1，2，4-三唑-1-丙腈，hexaconazole，cyproconazle，tebuconazole，diniconazole，氟代酰亚胺，吡啶-α-硫羟-1-氧化物，8-羟基喹啉硫酸盐及其金属盐，2，3-二氢-5-羧酰苯胺基-6-甲基-1，4-氧硫杂环己二烯-4，4-二氧化物，2，3-二氢-5-羧酰苯胺基-6-甲基-1，4-氧硫杂环己二烯顺-N-〔(1，1，2，2-四氯乙基)硫羟〕-4-环己烯-1，2-二羧酰亚胺，环己酰亚胺，脱氢乙酸，captafol，ethirimol，quinomethionateD，L-甲基-N-(2，6-二甲基苯基)-N-(2′-甲氧基乙酰基)丙氨酸甲酯；D，L-甲基-N-( 2，6-二甲基苯基)-N-氯代乙酰基-D，L-α-氨基丁酸内酯，D，L-N-(2，6-二甲基苯基)-N-(苯基乙酰基)丙氨酸甲酯，5-甲基-5-乙烯基-3-(3，5-二氯代苯基)-2，4-二氧代-1，3-噁唑烷，3-(3，5-二氯代苯基)-5-甲基-5-(甲氧基甲基)-1，3-噁唑烷-2，4-二酮，3-(3，5-二氯代苯基)-1-异丙基氨基甲酰基乙内酰脲，2-氰基-〔N-(乙基氨基羰基)-2-甲氧亚氨基〕乙酰胺，fenpropimorph，fenpropidine，2，6-二甲基-N-三癸基吗啉，dodemorph，和triforine；
(d)各种各样的卤代杀真菌剂例如：氯醌，二氯萘醌，地茂散(chloronebe)，杀草畏，TCPN氯硝胺，2-氯代-1-硝基丙烷，多氯代硝基苯例如，戊氯代硝基苯(PCNB)，以及四氟二氯丙酮；
(e)杀真菌的抗生素例如灰黄霉素，春雷霉素，多氧菌素，有效霉素，以及链霉素B；
(f)铜基的杀真菌剂例如：氢氧化铜，氧化亚铜，碱性氯化铜，碱性碳酸铜，对苯二甲酸铜，环烷酸铜以及枣红混合物，和
(g)多种杀真菌剂例如：十八烷胍，乙酸汞，N-乙基汞-1，2，3，6-四氢-3，6-endomethano-3，4，56，7，7-六氯代苯邻二甲酰亚胺，苯基汞单乙醇乳酸铵，对-二甲基氨基苯磺酸钠，异硫氰酸甲酯，1-硫氰基-2，4-二硝基苯，1-苯氨基硫脲，含镍的化合物，氰氨化钙，石灰硫磺，托布津-甲基，flutolanil，edinophos，富士一号，propenazole，以及三环唑。
1，2，4-三唑，及其对映体，酸加成盐和金属盐络合物可以各种各样的方式有利地使用。由于这些化合物具有广谱杀真菌活性，因此它们可用于谷物的储存。它们的络合物可以作为杀真菌剂，用于包括小麦，大麦，黑麦的禾谷类，用于稻子，花生，大豆，葡萄，用于草地，用于水果，坚果和蔬菜果园，以及用于高尔夫球场。本发明的化合物可抗病害的例子包括玉米和大麦的长蠕孢属，小麦和大麦的白粉病，小麦叶和茎的锈病，马铃薯早期亚麻枯萎病，花生早期叶点，葡萄白粉病，葡萄黑色腐烂，苹果斑点病，苹果白粉病，黄瓜白粉病，水果的褐色腐烂，葡萄孢属，大豆白粉病，黄瓜炭疽病，小麦颖枯病菌，稻叶鞘亚麻枯萎病，以及稻瘟病。
本发明的1，2，4-三唑的其它应用可为农业领域内的熟练技术人员所联想。
Claims (9)
1.一种下式的化合物或它们的农学上可接受的对映体，酸加成盐或金属盐络合物，其中Ar是苯基或在4-位上用卤素取代的苯基，
Z是C2-C12烷基，
X是-NC，-CH2N≡C，-CHO，-CON3，-CH＝NOH，-CH2NHCHO，-NHCHO，-NHCOCH3，-NH2或-CH＝CH2.
2.权利要求1的化合物，其中Z是C2-C6烷基。
3.根据权利要求2的化合物，该化合物是2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己基异氰化物。
4.根据权利要求2的化合物，该化合物是2-(4-氯代苯基)-2-(1，2，4-三唑-1-基)-2-己基异氰化物。
5.权利要求2的化合物，该化合物是2-(4-氯代苯基)-1-(1，2，4-三唑-1-基)-2-己胺。
6.权利要求2的化合物，该化合物是2-(4-氯代苯基)-2-〔(1，2，4-三唑-1-基)甲基〕己醛。
7.权利要求2的化合物，该化合物是3-(4-氯代苯基)-3-〔(1，2，4-三唑-1-基)甲基〕-1-庚烯。
8.一种杀真菌组合物，该组合物包括一种农业上可接受的载体，以及杀真菌有效量的权利要求1至7任一项的化合物。
9.一种控制真菌的方法，该方法包括向真菌所在地施用杀真菌有效量的权利要求1至7任一项的化合物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US900,047 | 1992-06-17 | ||
| US07/900,047 US5252594A (en) | 1992-06-17 | 1992-06-17 | Fungicidal (2-aryl-2-substituted)ethyl-1,2,4-triazoles |
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| Publication Number | Publication Date |
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| CN1082032A CN1082032A (zh) | 1994-02-16 |
| CN1035875C true CN1035875C (zh) | 1997-09-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93107221A Expired - Fee Related CN1035875C (zh) | 1992-06-17 | 1993-06-17 | 杀真菌的(2-芳基-2-取代的)乙基1，2，4-三唑 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5252594A (zh) |
| EP (1) | EP0575122A3 (zh) |
| JP (1) | JPH06107643A (zh) |
| KR (1) | KR940005592A (zh) |
| CN (1) | CN1035875C (zh) |
| AU (1) | AU671120B2 (zh) |
| BR (1) | BR9302380A (zh) |
| CA (1) | CA2098083A1 (zh) |
| HU (1) | HU214226B (zh) |
| IL (1) | IL106012A0 (zh) |
| NZ (1) | NZ247885A (zh) |
| TR (1) | TR26895A (zh) |
| TW (1) | TW255889B (zh) |
| ZA (1) | ZA934324B (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9116672D0 (en) * | 1991-08-01 | 1991-09-18 | Hickson Int Plc | Preservatives for wood and other cellulosic materials |
| US5527384A (en) * | 1991-08-01 | 1996-06-18 | Hickson International, Plc | Preservatives for wood and other cellulosic materials |
| US5358939A (en) * | 1992-06-25 | 1994-10-25 | Rohm And Haas Company | Fungicidal 2-aryl-2,2-disubstituted ethyl-1,2,4-triazoles |
| DE4412358A1 (de) * | 1994-04-11 | 1995-10-12 | Bayer Ag | Cyclopropyl-ethyl-azole |
| IL115889A0 (en) * | 1994-11-14 | 1996-01-31 | Rohm & Haas | Pyridazinones and their use as fungicides |
| US6121251A (en) * | 1996-10-11 | 2000-09-19 | Rohm And Haas Company | Dihydropyridazinones and pyridazinones and their use as fungicides and insecticides |
| AU730346B2 (en) * | 1997-07-03 | 2001-03-08 | Dow Agrosciences Llc | Benzyloxy substituted aromatics and their use as fungicides and insecticides |
| EP1553831A4 (en) * | 2002-06-17 | 2007-11-07 | Dow Agrosciences Llc | PROCESS FOR SCREENING FUNGITOXIC COMPOUNDS |
| CN114957215B (zh) * | 2022-01-13 | 2023-03-21 | 渤海大学 | 亚甲基桥连喹啉和1,2,3-三唑双杂环化合物及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4598085A (en) * | 1977-04-27 | 1986-07-01 | Janssen Pharmaceutica N.V. | Fungicidal 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles |
| US4366165A (en) * | 1977-05-19 | 1982-12-28 | Rohm And Haas Company | 1 and 4-Arylcyanoalkyl-1,2,4-triazoles and fungicidal use |
| EP0052424B2 (en) * | 1980-11-19 | 1990-02-28 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| US4398942A (en) * | 1980-12-22 | 1983-08-16 | Rohm And Haas Company | Herbicidally-active phenylacetonitriles |
| CA1189857A (en) * | 1981-03-27 | 1985-07-02 | Janssen Pharmaceutica Naamloze Vennootschap | Antimicrobial triazole derivatives |
| GB2104065B (en) * | 1981-06-04 | 1985-11-06 | Ciba Geigy Ag | Heterocyclyl-substituted mandelic acid compounds and mandelonitriles and their use for combating microorganisms |
| US4466974A (en) * | 1982-11-16 | 1984-08-21 | Pfizer Inc. | Bistriazole antifungal agents |
| CH655103A5 (de) * | 1983-03-11 | 1986-03-27 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und ihre verwendung. |
| DE3407005A1 (de) * | 1983-09-26 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Hydroxyethylazolyl-oxim-derivate |
| FR2557875B1 (fr) * | 1984-01-11 | 1986-04-25 | Jouveinal Sa | Aminoethylimidazole, composition pharmaceutique en contenant et procede de preparation |
| DE3835742A1 (de) * | 1988-10-20 | 1990-05-10 | Lentia Gmbh | Neue nitroalkylazole |
| GB9125791D0 (en) * | 1991-12-04 | 1992-02-05 | Schering Agrochemicals Ltd | Herbicides |
-
1992
- 1992-06-17 US US07/900,047 patent/US5252594A/en not_active Expired - Fee Related
-
1993
- 1993-05-31 TW TW082104291A patent/TW255889B/zh active
- 1993-06-09 CA CA002098083A patent/CA2098083A1/en not_active Abandoned
- 1993-06-11 EP EP19930304578 patent/EP0575122A3/en not_active Ceased
- 1993-06-14 IL IL106012A patent/IL106012A0/xx unknown
- 1993-06-15 KR KR1019930010871A patent/KR940005592A/ko not_active Withdrawn
- 1993-06-15 NZ NZ247885A patent/NZ247885A/en unknown
- 1993-06-16 AU AU41306/93A patent/AU671120B2/en not_active Ceased
- 1993-06-16 JP JP5145231A patent/JPH06107643A/ja not_active Withdrawn
- 1993-06-16 HU HUP9301756A patent/HU214226B/hu not_active IP Right Cessation
- 1993-06-16 BR BR9302380A patent/BR9302380A/pt not_active Application Discontinuation
- 1993-06-17 CN CN93107221A patent/CN1035875C/zh not_active Expired - Fee Related
- 1993-06-17 ZA ZA934324A patent/ZA934324B/xx unknown
- 1993-06-17 TR TR00484/93A patent/TR26895A/xx unknown
- 1993-09-17 US US08/097,242 patent/US5364870A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ZA934324B (en) | 1994-01-13 |
| EP0575122A2 (en) | 1993-12-22 |
| HU214226B (hu) | 1998-01-28 |
| KR940005592A (ko) | 1994-03-21 |
| AU4130693A (en) | 1993-12-23 |
| US5252594A (en) | 1993-10-12 |
| JPH06107643A (ja) | 1994-04-19 |
| HU9301756D0 (en) | 1993-09-28 |
| HUT66391A (en) | 1994-11-28 |
| TW255889B (zh) | 1995-09-01 |
| CN1082032A (zh) | 1994-02-16 |
| NZ247885A (en) | 1996-02-27 |
| AU671120B2 (en) | 1996-08-15 |
| CA2098083A1 (en) | 1993-12-18 |
| US5364870A (en) | 1994-11-15 |
| TR26895A (tr) | 1994-08-22 |
| BR9302380A (pt) | 1994-01-11 |
| EP0575122A3 (en) | 1994-05-25 |
| IL106012A0 (en) | 1993-10-20 |
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