CN1216441A - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
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- CN1216441A CN1216441A CN97194055A CN97194055A CN1216441A CN 1216441 A CN1216441 A CN 1216441A CN 97194055 A CN97194055 A CN 97194055A CN 97194055 A CN97194055 A CN 97194055A CN 1216441 A CN1216441 A CN 1216441A
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- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
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- 235000016213 coffee Nutrition 0.000 description 1
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- 230000001276 controlling effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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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
- 239000011777 magnesium Substances 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- 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)
- Indole Compounds (AREA)
Abstract
杀真菌混合物,它包含增效活性量的至少一种式(Ⅰ)和(Ⅱ)的化合物:a1)式Ⅰ的肟醚,其中,X是氧或氨基(NH);Y是CH或N;Z是氧、硫、氨基(NH)或C1－C4－烷基氨基(N－C1－C4－烷基);R’是C1－C6－烷基、C1－C6－卤代烷基、C3－C6－链烯基、C2－C6－卤代链烯基、C3－C6－炔基、C3－C6－卤代炔基、C3－C6－环烷基甲基或苄基,后者可以部分或全部卤代和/或可以带有一至三个下列基团:氰基、C1－C4－烷基、C1－C4－卤代烷基、C1－C4－烷氧基、C1－C4－卤代烷氧基和C1－C4－烷硫基;a2)式Ⅱ的氨基甲酸酯,其中T是CH或N,n是0、1或2且R是卤素、C1－C4－烷基或C1－C4－卤代烷基,当n是2时基团R可以不同,和b)选自化合物Ⅲ和Ⅳ的邻苯二甲酰亚胺衍生物。
Description
本发明涉及杀真菌混合物，它包含增效活性量的a1)和a2)中的至少一种化合物
a1)式Ⅰ的肟醚
其中取代基具有下列含意：
X是氧或氨基(NH)；
Y是CH或N；
Z是氧、硫、氨基(NH)或C1-C4-烷基氨基(N-C1-C4-烷基)；
R’是C1-C6-烷基、C1-C6-卤代烷基、C3-C6-链烯基、C2-C6-卤代链烯基、C3-C6-炔基、C3-C6-卤代炔基、C3-C6-环烷基甲基或苄基，该苄基可以部分或全部卤化和/或可以带有一至三个下列基团：氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基和C1-C4-烷硫基；
a2)式Ⅱ的氨基甲酸酯
其中T是CH或N,n是0、1或2且R是卤素、C1-C4-烷基或C1-C4-卤代烷基，当n是2时基团R可以不同，
以及
b)选自化合物Ⅲ和Ⅳ的邻苯二甲酰亚胺衍生物
而且，本发明还涉及使用化合物Ⅰ或Ⅱ与Ⅲ、或者Ⅰ或Ⅱ与Ⅳ的混合物防治有害真菌的方法，以及涉及化合物Ⅰ、化合物Ⅱ和化合物Ⅲ和Ⅳ制备这些混合物的应用。
式Ⅰ化合物、其制备和其对有害真菌的作用也已公开于文献中(WO-A 95/21,153、WO 95/21 154和DE-A 19 528 651.0)。
式Ⅱ化合物、其制备和其对有害真菌的作用已公开于文献中(WO-A 96/01,256和WO-A 96/01,258)。
邻苯二甲酰亚胺衍生物Ⅲ和Ⅳ(US-A2,553,770；2,553,771；2,553,776)、其制备和其对有害真菌的作用也已公开。
本发明的目的是提供对有害真菌具有改进作用且降低施用活性成分总量的混合物(增效混合物)，目的在于使这些已知化合物施用量降低并且改进其作用谱。
因此，我们发现此目的通过开头定义的混合物实现。而且，我们发现，通过同时一起或分别施用化合物Ⅰ或Ⅱ和化合物Ⅲ或化合物Ⅳ，或依次施用化合物Ⅰ或Ⅱ和化合物Ⅲ或化合物Ⅳ，可以比使用单独的化合物更好地防治有害真菌。
特别是，在通式Ⅰ代表的化合物中，优选其中X是氧且Y是CH或者其中X是氨基且Y是N的肟醚。
此外，优选的是那些其中Z是氧的化合物Ⅰ。
同样，优选的是那些其中R’是烷基或苄基的化合物Ⅰ。
对于其在本发明增效混合物中的应用而言，特别优选的化合物Ⅰ是汇集于下表中的那些：
表1．
式ⅠA化合物，其中对于每一化合物，ZR’相应于表A中的一行
表2．
式ⅠB化合物，其中对于每一化合物而言，ZR’相应于表A中的一行
表A：
| 序号 | ZR′ |
| Ⅰ.1 | O-CH2CH2CH3 |
| Ⅰ.2 | O-CH(CH3)2 |
| Ⅰ.3 | O-CH2CH2CH2CH3 |
| Ⅰ.4 | O-CH(CH3)CH2CH3 |
| Ⅰ.5 | O-CH2CH(CH3)2 |
| Ⅰ.6 | O-C(CH3)3 |
| Ⅰ.7 | S-C(CH3)3 |
| Ⅰ.8 | O-CH(CH3)CH2CH2CH3 |
| Ⅰ.9 | O-CH2C(CH3)3 |
| Ⅰ.10 | O-CH2C(Cl)=CCl2 |
| Ⅰ.11 | O-CH2CH=CH-Cl(trans) |
| Ⅰ.12 | O-CH2C(CH3)=CH2 |
| Ⅰ.13 | O-CH2-(cyclopropyl) |
| Ⅰ.14 | O-CH2-C6H5 |
| Ⅰ.15 | O-CH2-[4-F-C6H4] |
| Ⅰ.16 | O-CH2CH3 |
| Ⅰ.17 | O-CH(CH2CH3)2 |
由于存在C=Y双键，式Ⅰ化合物可以存在E或Z构形(相对于羧酸官能团)。因此，在每一种情况下，它们可以以纯E或Z异构体或以E/Z异构体混合物用于本发明混合物中。优选使用E/Z异构体混合物或E异构体，特别优选的是E异构体。
化合物Ⅰ的侧链上的肟醚基团的C=N双键在每一种情况下可以纯E或Z异构体或E/Z异构体混合物形式存在。化合物Ⅰ可以以其异构体混合物或纯异构体使用于本发明混合物中。对于其使用而言，特别优选的化合物Ⅰ是那些其中在侧链上的未端肟醚基是顺式构形(OCH3基团相对于ZR’)的化合物Ⅰ。
特别是，在式Ⅱ代表的氨基甲酸酯中，优选其中取代基的组合相应于下文表中的一行：
表3
| 序号 | X | Rn |
| Ⅱ.1 | N | 2-F |
| Ⅱ.2 | N | 3-F |
| Ⅱ.3 | N | 4-F |
| Ⅱ.4 | N | 2-Cl |
| Ⅱ.5 | N | 3-Cl |
| Ⅱ.6 | N | 4-Cl |
| 序号 | X | Rn |
| Ⅱ.7 | N | 2-Br |
| Ⅱ.8 | N | 3-Br |
| Ⅱ.9 | N | 4-Br |
| Ⅱ.10 | N | 2-CH3 |
| Ⅱ.11 | N | 3-CH3 |
| Ⅱ.12 | N | 4-CH3 |
| Ⅱ.13 | N | 2-CH2CH3 |
| Ⅱ.14 | N | 3-CH2CH3 |
| Ⅱ.15 | N | 4-CH2CH3 |
| Ⅱ.16 | N | 2-CH(CH3)2 |
| Ⅱ.17 | N | 3-CH(CH3)2 |
| Ⅱ.18 | N | 4-CH(CH3)2 |
| Ⅱ.19 | N | 2-CF3 |
| Ⅱ.20 | N | 3-CF3 |
| Ⅱ.21 | N | 4-CF3 |
| Ⅱ.22 | N | 2,4-F2 |
| Ⅱ.23 | N | 2,4-Cl2 |
| Ⅱ.24 | N | 3,4-Cl2 |
| Ⅱ.25 | N | 2-Cl,4-CH3 |
| Ⅱ.26 | N | 3-Cl,4-CH3 |
| Ⅱ.27 | CH | 2-F |
| Ⅱ.28 | CH | 3-F |
| Ⅱ.29 | CH | 4-F |
| Ⅱ.30 | CH | 2-Cl |
| Ⅱ.31 | CH | 3-Cl |
| Ⅱ.32 | CH | 4-Cl |
| Ⅱ.33 | CH | 2-Br |
| Ⅱ.34 | CH | 3-Br |
| Ⅱ.35 | CH | 4-Br |
| Ⅱ.36 | CH | 2-CH3 |
| Ⅱ.37 | CH | 3-CH3 |
| Ⅱ.38 | CH | 4-CH3 |
| Ⅱ.39 | CH | 2-CH2CH3 |
| Ⅱ.40 | CH | 3-CH2CH3 |
| Ⅱ.41 | CH | 4-CH2CH3 |
| Ⅱ.42 | CH | 2-CH(CH3)2 |
| Ⅱ.43 | CH | 3-CH(CH3)2 |
| Ⅱ.44 | CH | 4-CH(CH3)2 |
| Ⅱ.45 | CH | 2-CF3 |
| 序号 | X | Rn |
| Ⅱ.46 | CH | 3-CF3 |
| Ⅱ.47 | CH | 4-CF3 |
| Ⅱ.48 | CH | 2,4-F2 |
| Ⅱ.49 | CH | 2,4-Cl2 |
| Ⅱ.50 | CH | 3,4-Cl2 |
| Ⅱ.51 | CH | 2-Cl,4-CH3 |
| Ⅱ.52 | CH | 3-Cl,4-CH3 |
化合物Ⅱ.12、Ⅱ.23、Ⅱ.32和Ⅱ.38是特别优选的。
由于它们的基本特性，化合物Ⅰ和Ⅱ能够与无机或有机酸或与金属离子形成加成物或盐。
无机酸的实例是氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸，硫酸、磷酸和硝酸。
适合的有机酸是(例如)甲酸、碳酸和链烷酸如乙酸、三氟乙酸、三氯乙酸和丙酸，以及乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(具有1至20个碳原子的直链或支链烷基基团的磺酸)、芳基磺酸或芳基二磺酸(芳族基团如苯基和萘基，它们具有一或二个连于其上的磺基基团)、烷基膦酸(具有1至20个碳原子的直链或支链烷基基团的膦酸)、芳基膦酸或芳基二膦酸(芳族基团如苯基和萘基，它们具有一或二个连于其上的膦酸残基)，对于烷基或芳基基团，也可能有另外的取代基连于其上，例如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
适合的金属离子(特别)是第二主族元素、特别是钙和镁，第三和第四主族元素、特别是铝、锡和铅，和第一至八副族元素、特别是铬、锰、铁、钴、镍、铜、锌及其它的离子。特别优选的是第四周期各副组元素的金属离子。这些金属可以以各种它们可以出现的价位存在。
当制备混合物时，优选的是采用纯的活性成分Ⅰ和Ⅱ或Ⅲ和Ⅳ，且如果需要的话，它们可以与其它的杀有害真菌或其它害虫如昆虫、蜱螨或线虫的活性成分，或是与除草的或生长调节的活性成分或化肥混合。
化合物Ⅰ和/或Ⅱ和Ⅲ、或者Ⅰ和/或Ⅱ和Ⅳ的混合物，或同时一起或分别使用的化合物Ⅰ和/或Ⅱ和Ⅲ、或者Ⅰ和/或Ⅱ和Ⅳ，对广谱的植物病原真菌，特别是对子囊菌纲、半知菌纲、担子菌纲和藻状菌纲有突出的作用。它们中的一些有内吸作用，因此可以用作叶面和土壤作用的杀真菌剂。
它们在防治各种作物如棉花、蔬菜(例如黄瓜、豆和胡瓜)、大麦、禾草、燕麦、咖啡、玉米、水果、稻、黑麦、大豆、葡萄、小麦、观赏植物、甘蔗和各种种子上的许多植物病原真菌方面特别重要。
它们特别适合于防治下列植物病原真菌：禾谷类上的禾白粉菌(Erysiphe graminia)，胡瓜上的二孢白粉菌(Erysiphe cichoracearum)和苍耳单丝壳菌(Sphaerotheca fuliginea)，苹果上的苹果白粉病柄球菌(Podosphaera leucotricha)，禾谷类上的柄锈菌(Puccinia)，棉花、稻和草坪上的丝核菌(Rhizoctonia)，禾谷类和甘蔗上的黑粉菌(Ustilago)，苹果上的苹果黑星菌(Venturia Inaequalis)，禾谷类上的长蠕孢菌(Helminthosporium)，小麦上的颖枯病菌(Septoria nodorum)，草莓、蔬菜、观赏植物和葡萄上的灰霉菌(Botrytis cinera)，花生上的花生尾孢菌(Cercospora arachidicola)，小麦和大麦上的眼斑病菌(Pseudocercospora herpotophthora)，稻上的稻梨孢(Pyriculariaoryzae)，马铃薯和蕃茄上的蔓延疫霉(Phytophthora infestans)，胡瓜和蛇麻草上的假霜霉(Pseudoperonospora)，葡萄上的葡萄生单轴霉(Plasmopara viticola)，蔬菜和水果上的链格孢菌(Alternaria)，以及镰刀菌(Fusarium)和轮枝孢菌(Verticillium)。
它们也可以用在材料的保护上(例如，木材防腐)，例如防治宛氏拟青霉(Paecilomhces variotii)。
化合物Ⅰ和/或Ⅱ和Ⅲ、或者Ⅰ和/或Ⅱ和Ⅳ可以同时一起或分别或依次施用，在分别施用时，施用顺序通常不影响防治措施的效果。
化合物Ⅰ和/或Ⅱ和Ⅲ、或者Ⅰ和/或Ⅱ和Ⅳ通常以1∶1至1∶100、优选1∶1至1∶50、特别是1∶3至1∶30(Ⅰ或Ⅱ∶Ⅲ或Ⅳ)的重量比使用。
依据所需的效果的性质的不同，本发明混合物的使用量通常为0.02至5千克/公顷，优选0.05至3.5千克/公顷，特别是0.1至3.5千克/公顷。
在化合物Ⅰ和/或Ⅱ的情况下，施用量一般是0.005至0.5千克/公顷，优选是0.01至0.5千克/公顷，特别是0.01至0.3千克/公顷。
相应地，在化合物Ⅲ或化合物Ⅳ的情况下，施用量是0.1至5千克/公顷，优选0.1至3.5千克/公顷。
处理种子时，混合物的施用量通常是0.001至50克/千克种子，优选0.01至10克/千克种子，特别是0.01至5克/千克种子。
如果意欲防治的是植物病原真菌，则通过向种子、植物或播种前或播种后植物出芽前或后的土壤喷雾或喷粉，分别或一起施用化合物Ⅰ和/或Ⅱ和Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ，或者化合物Ⅰ和/或Ⅱ与Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ的混合物。
本发明的增效混合物或化合物Ⅰ和/或Ⅱ与Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ可以加工成(例如)可直接喷雾溶液、粉末和悬浮液形式，或高浓度水悬剂、油悬剂或其它悬浮剂、分散液、乳液、油分散液、膏剂、粉剂、撒施剂或颗粒剂，并可通过喷雾、弥雾、喷粉、撒施或浇泼使用。施用形式取决于使用的目的；在每一种情况下，应确保本发明混合物的分散尽可能的细微和均匀。
制剂以其本身已知的方式来生产，例如，添加溶剂和/或载体。惰性添加剂如乳化剂或分散剂通常用来与制剂混合。
适合的表面活性剂是芳族磺酸例如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐，和脂肪酸、烷基磺酸和烷基芳基磺酸、烷基硫酸、月桂基醚硫酸和脂肪醇硫酸的碱金属盐、碱土金属盐和铵盐，以及硫酸化的十六-、十七-和十八烷醇或脂肪醇二醇醚的盐，磺化萘和其衍生物与甲醛的缩合产物，萘或萘磺酸与苯酚和甲醛的缩合产物，聚氧乙烯辛基酚醚，乙氧基化的异辛基-、辛基-或壬基酚，烷基苯酚或三丁基苯基聚二醇醚，烷基芳基聚醚醇，异十三烷醇、脂肪醇/环氧乙烷缩合物，乙氧基化蓖麻油，聚氧乙烯烷基醚或聚氧丙烯，月桂醇聚二醇醚乙酸酯，失水山梨醇酯，木素亚硫酸盐废液或甲基纤维素。
粉剂、撒施材料和喷粉剂可以通过将化合物Ⅰ和/或Ⅱ与Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ，或者化合物Ⅰ和/或Ⅱ与Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ的混合物与固体载体混合或一起研磨而制备。
颗粒剂(例如，涂敷、浸渍或均质颗粒剂)通常是通过将一种或多种活性化合物结合到固体载体上而制备的。
可以使用的填料和固体载体的实例是矿石土如硅胶、二氧化硅、硅胶类、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁，研磨的合成材料，和化肥如硫酸铵、磷酸铵、硝酸铵、尿素，以及植物产品如面粉、树皮粉、木粉和坚果壳粉、纤维素粉，或者其它固体载体。
制剂中通常含有0.1至95％(重量)、优选0.5至90％(重量)的化合物Ⅰ和/或Ⅱ与Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ之一，或者化合物Ⅰ和/或Ⅱ与Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ的混合物。采用的活性成分纯度为90％至100％，优选95％至100％(根据NMR或HPLC谱)。
化合物Ⅰ和/或Ⅱ或Ⅲ、或Ⅰ和/或Ⅱ或Ⅳ、或混合物或相应的制剂，是通过使用杀真菌活性量的混合物，或(在分别施用的情况下)使用杀真菌活性量的化合物Ⅰ和/或Ⅱ和Ⅲ、或Ⅰ和/或Ⅱ和Ⅳ，处理真菌或处理意欲防除有害真菌的植物、种子、土壤、区域、材料或空间来施用的。施用可以在有害真菌侵染前或后进行。
这些化合物与混合物的杀真菌活性用下列实验来说明：
活性成分分别或一起加工成于下列混合物中的浓度为10％的乳剂：70％(重量)的环己酮、20％(重量)的NekanilLN(LutensolAP6，基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)和10％(重量)的EmulphorEL(EmulanEL，基于乙氧基化脂肪醇的乳化剂)。并用水稀释至所需浓度。
通过确定感病的叶面积百分率进行评价，并将这些百分率值转化成效力。活性成分混合物的预期效力是用Colby公式来计算[R.S.Colby，《杂草(Weeds)》15,20-22(1967)]，并与实测效力作比较。
Colby公式：
E=x+y-xy/100
E以浓度a与b使用活性成分A与B的混合物时的预期效力，以相对于未处理对照的％表示
x以浓度a使用活性成分A时的效力，以相对于未处理对照的％表示
y以浓度b使用活性成分B时的效力，以相对于未处理的％表示。
效力(
W)使用Abbot公式计算
W=(1-α)100/β
α是处理植物的真菌感染％
β是未处理植物对照的真菌感染％。
效力为0指感染程度与未处理对照的相同；效力为100指处理的植物未感染。
实施例1至21
对柿子椒灰霉病(Botrytis cinerea)的效力
在4至5个叶片完全长成后，将栽培品种“Neusiedler Ideal Elite”的柿子椒秧用由10％活性成分、63％环己酮和27％乳化剂的母液制备出的活性化合物的含水制剂喷雾直到雾滴向下滴流点。第二天，将处理的植株用于2％浓度的Biomalz溶液中的含有1.7×106孢子/ml的灰霉病菌(Botrytis cinerea)的孢子悬浮液接种。将试验植株放置在22-24℃和高空气湿度下的环境控制室中。5天后，目测确定叶片上的真菌发病程度。
结果示于表4中。
表4
| 实施例 | 活性成分 | 喷雾混合物中的活性成分浓度(ppm) | 相对于未处理对照的效力％ |
| 1Ⅴ | 对照(未处理) | (病害水平99％) | 0 |
| 2Ⅴ | A=表1A,No.2 | 502512.5 | 000 |
| 3Ⅴ | B=表1A,No.4 | 502512.5 | 000 |
| 4Ⅴ | Ⅲ=克菌丹 | 2512.5 | 00 |
| 5Ⅴ | Ⅳ=Folpet | 2512.5 | 00 |
表5
*)根据colby公式计算
| 实施例 | 喷雾混合物中的混合物：活性成分浓度(ppm) | 实测效力 | 计算效力*) |
| 6 | 50A+25Ⅲ | 70 | 0 |
| 7 | 25A+12.5Ⅲ | 30 | 0 |
| 8 | 25A+25Ⅲ | 97 | 0 |
| 9 | 12.5A+12.5Ⅲ | 50 | 0 |
| 10 | 50A+25Ⅳ | 90 | 0 |
| 11 | 25A+12.5Ⅳ | 20 | 0 |
| 12 | 25A+25Ⅳ | 97 | 0 |
| 13 | 12.5A+12.5Ⅳ | 20 | 0 |
| 14 | 50B+25Ⅲ | 80 | 0 |
| 15 | 25B+12.5Ⅲ | 40 | 0 |
| 16 | 25B+25Ⅲ | 95 | 0 |
| 17 | 12.5B+12.5Ⅲ | 30 | 0 |
| 18 | 50B+25Ⅳ | 90 | 0 |
| 19 | 25B+12.5Ⅳ | 80 | 0 |
| 20 | 25B+25Ⅳ | 80 | 0 |
| 21 | 12.5B+12.5Ⅳ | 70 | 0 |
实施例22-42
对柿子椒灰霉病(Botrytis cinerea)的效力
将绿柿子椒果盘用由10％活性成分、63％环己酮和27％乳化剂的母液制备出的活性化合物的含水制剂喷雾直到雾滴向下滴流点。在喷雾液层变干2小时后，将果盘用于2％浓度的Biomalz溶液中的含有1.7×106孢子/ml的灰霉病菌(Botrytis cinerea)的孢子悬浮液接种。接种的果盘随后在18℃的保湿室中培养4天。随后目测评价果盘的灰霉菌感染程度。
表6
| 实施例 | 活性成分 | 喷雾混合物中的活性成分浓度(ppm) | 相对于未处理对照的效力％ |
| 22Ⅴ | 对照(未处理) | (病害水平99％) | 0 |
| 23Ⅴ | A | 2001002512.5 | 2950199 |
| 24Ⅴ | B | 502512.5 | 50399 |
| 25Ⅴ | Ⅲ=克菌丹 | 1002512.5 | 1999 |
| 26Ⅴ | Ⅳ=Folpet | 1002512.5 | 2990 |
表7
*)根据colby公式计算
| 实施例 | 喷雾混合物中的混合物：活性成分浓度(ppm) | 实测效力 | 计算效力*) |
| 27 | 200A+100Ⅲ | 95 | 43 |
| 28 | 25A+12.5Ⅲ | 60 | 27 |
| 29 | 100A+100Ⅲ | 90 | 59 |
| 30 | 25A+25Ⅲ | 50 | 27 |
| 31 | 200A+100Ⅳ | 95 | 50 |
| 32 | 25A+12.5Ⅳ | 39 | 19 |
| 33 | 25A+25Ⅳ | 60 | 27 |
| 34 | 12.5A+12.5Ⅳ | 29 | 9 |
| 35 | 50B+25Ⅲ | 85 | 54 |
| 36 | 25B+12.5Ⅲ | 70 | 45 |
| 37 | 50B+50Ⅲ | 97 | 59 |
| 38 | 25B+25Ⅲ | 80 | 45 |
| 39 | 50B+25Ⅳ | 85 | 54 |
| 40 | 25B+12.5Ⅳ | 85 | 39 |
| 41 | 25B+25Ⅳ | 85 | 45 |
| 42 | 12.5B+12.5Ⅳ | 70 | 9 |
实施例1至42的结果表明，所有混合比率的观察效力均超过用Colby公式计算得到的效力。
实施例43至58
对柿子椒灰霉病(Botrytis cinerea)的效力
在4至5个叶片完全长成后，将栽培品种“Neusiedler Ideal Elite”的柿子椒秧用由10％活性成分、63％环己酮和27％乳化剂的母液制备出的活性化合物的含水制剂喷雾直到雾滴向下滴流点。第二天，将处理的植株用于2％浓度的Biomalz溶液中的含有1.7×106孢子/ml的灰霉病菌(Botrytis cinerea)的孢子悬浮液接种。将试验植株放置在22-24℃和高空气湿度下的环境控制室中。5天后，目测确定叶片上的真菌发病程度。
表8
| 实施例 | 活性成分 | 喷雾混合物中的活性成分浓度(ppm) | 相对于未处理对照的效力％ |
| 43Ⅴ | 对照(未处理) | (病害水平99％) | 0 |
| 44Ⅴ | c= 化合物Ⅱ.32 | 502512.5 | 808050 |
| 45Ⅴ | D= 化合物Ⅱ.38 | 502512.5 | 30300 |
| 46Ⅴ | Ⅲ=克菌丹 | 2512.5 | 00 |
| 47Ⅴ | Ⅳ=Folpet | 2512.5 | 00 |
表9
*)根据colby公式计算
| 实施例 | 喷雾混合物中的活性成分浓度(ppm) | 实测效力 | 计算效力*) |
| 48 | 50C+25Ⅲ | 97 | 80 |
| 49 | 25C+25Ⅲ | 99 | 80 |
| 50 | 50C+25Ⅳ | 90 | 80 |
| 51 | 25C+25Ⅳ | 97 | 80 |
| 52 | 12.5C+12.5Ⅳ | 95 | 50 |
| 53 | 25D+25Ⅲ | 98 | 29 |
| 54 | 12.5D+12.5Ⅲ | 97 | 0 |
| 55 | 50D+25Ⅳ | 95 | 29 |
| 56 | 25D+12.5Ⅳ | 70 | 29 |
| 57 | 25D+25Ⅳ | 98 | 29 |
| 58 | 12.5D+12.5Ⅳ | 85 | 0 |
实施例59-79
对柿子椒灰霉病(Botrytis cinerea)的效力
将绿柿子椒果盘用由10％活性成分、63％环己酮和27％乳化剂的母液制备出的活性化合物的含水制剂喷雾直到雾滴向下滴流点。在喷雾液层变干2小时后，将果盘用于2％浓度的Biomalz溶液中的含有1.7×106孢子/ml的灰霉病菌(Botrytis cinerea)的孢子悬浮液接种。接种的果盘随后在18℃的保湿室中培养4天。随后目测评价果盘的灰霉菌感染程度。
表10
| 实施例 | 活性成分 | 喷雾混合物中的活性成分浓度(ppm) | 相对于未处理对照的效力％ |
| 59Ⅴ | 对照(未处理) | (病害水平99％) | 0 |
| 60Ⅴ | C=表3中的化合物Ⅱ.32 | 10025 | 5050 |
| 61Ⅴ | D=表3中的化合物Ⅱ.38 | 502512.5 | 50399 |
| 62Ⅴ | Ⅲ=克菌丹 | 200100502512.5 | 2919999 |
| 63Ⅴ | Ⅳ=Folpet | 100502512.5 | 291990 |
| 实施例 | 喷雾混合物中的活性成分浓度(ppm) | 实测效力 | 计算效力*) |
| 64 | 100C+50Ⅲ | 95 | 59 |
| 65 | 25C+12.5Ⅲ | 80 | 54 |
| 66 | 100C+100Ⅲ | 95 | 59 |
| 67 | 25C+25Ⅱ | 90 | 54 |
| 68 | 100C+50Ⅳ | 90 | 59 |
| 69 | 25C+12.5Ⅳ | 80 | 50 |
| 70 | 100C+100Ⅳ | 95 | 64 |
| 71 | 25C+25Ⅳ | 70 | 54 |
| 72 | 200D+100Ⅲ | 80 | 43 |
| 73 | 50D+25Ⅲ | 60 | 18 |
| 74 | 50D+50Ⅲ | 90 | 27 |
| 75 | 25D+25Ⅲ | 80 | 18 |
| 76 | 100D+50Ⅳ | 80 | 35 |
| 77 | 50D+25Ⅳ | 50 | 18 |
| 78 | 100D+100Ⅳ | 80 | 43 |
| 79 | 25D+25Ⅳ | 50 | 18 |
所有实施例的结果均表明，所有混合比率的观察效力均超过用Colby公式计算得到的效力。
Claims (7)
1．杀真菌混合物，它包含增效活性量的
a)至少一种选自a1)和a2)的化合物：
a1)式Ⅰ的肟醚
其中取代基具有下列含意：
X是氧或氨基(NH)；
Y是CH或N；
Z是氧、硫、氨基(NH)或C1-C4-烷基氨基(N-C1-C4-烷基)；
R’是C1-C6-烷基、C1-C6-卤代烷基、C3-C6-链烯基、C2-C6-卤代链烯基、C3-C6-炔基、C3-C6-卤代炔基、C3-C6-环烷基甲基或苄基，该苄基可以部分或全部卤化和/或可以带有一至三个下列基团：氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基和C1-C4-烷硫基；
a2)式Ⅱ的氨基甲酸酯
其中T是CH或N,n是0、1或2且R是卤素、C1-C4-烷基或C1-C4-卤代烷基，当n是2时基团R可以不同，和
b)选自化合物Ⅲ和Ⅳ的邻苯二甲酰亚胺衍生物
2．根据权利要求1的杀真菌混合物，它包含权利要求1中所述的式Ⅰ或Ⅱ化合物和邻苯二甲酰亚胺衍生物Ⅲ。
3．根据权利要求1的杀真菌混合物，它包含权利要求1中所述的式Ⅰ或Ⅱ化合物和邻苯二甲酰亚胺衍生物Ⅳ。
4．根据权利要求1的杀真菌混合物，其中化合物Ⅰ或Ⅱ与化合物Ⅲ或化合物Ⅳ的重量比是1∶1至1∶100。
5．防治有害真菌的方法，它包括用权利要求1中所述的式Ⅰ或Ⅱ化合物以及权利要求1所述的式Ⅲ化合物或权利要求1中所述的式Ⅳ化合物处理有害真菌、它们的环境或者意欲不受真菌侵染的植物、种子、土壤、区域、材料或空间。
6．根据权利要求5的方法，其中权利要求1中所述的化合物Ⅰ或Ⅱ以0.005至0.5千克/公顷的量处理有害真菌、它们的环境或者意欲不受真菌侵染的植物、种子、土壤、区域、材料或空间。
7．根据权利要求5的方法，其中权利要求1中所述的化合物Ⅲ或化合物Ⅳ以0.1至5千克/公顷的量处理有害真菌、它们的环境或者意欲不受真菌侵染的植物、种子、土壤、区域、材料或空间。
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19616684.5 | 1996-04-26 | ||
| DE19616684 | 1996-04-26 | ||
| DE19617233.0 | 1996-04-30 | ||
| DE19617233 | 1996-04-30 | ||
| DE19635518.4 | 1996-09-02 | ||
| DE19635518 | 1996-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1216441A true CN1216441A (zh) | 1999-05-12 |
Family
ID=27216185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97194055A Pending CN1216441A (zh) | 1996-04-26 | 1997-04-03 | 杀真菌混合物 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6083970A (zh) |
| EP (1) | EP0900008B1 (zh) |
| JP (1) | JP3810093B2 (zh) |
| KR (1) | KR20000065012A (zh) |
| CN (1) | CN1216441A (zh) |
| AR (1) | AR006855A1 (zh) |
| AT (1) | ATE219882T1 (zh) |
| AU (1) | AU732286B2 (zh) |
| BR (1) | BR9708831A (zh) |
| CA (1) | CA2252534A1 (zh) |
| CO (1) | CO4761032A1 (zh) |
| CZ (1) | CZ330898A3 (zh) |
| DE (1) | DE59707655D1 (zh) |
| DK (1) | DK0900008T3 (zh) |
| EA (1) | EA000837B1 (zh) |
| IL (1) | IL126233A (zh) |
| NZ (1) | NZ332099A (zh) |
| PL (1) | PL329504A1 (zh) |
| SK (1) | SK140998A3 (zh) |
| TW (1) | TW340034B (zh) |
| WO (1) | WO1997040672A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102696646A (zh) * | 2012-06-29 | 2012-10-03 | 陕西上格之路生物科学有限公司 | 一种含克菌丹的杀菌组合物 |
| CN106857599A (zh) * | 2017-04-27 | 2017-06-20 | 广东广康生化科技股份有限公司 | 一种含有吡唑醚菌酯和灭菌丹的杀菌组合物及其应用 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9809959A (pt) * | 1997-06-06 | 2000-08-01 | Basf Ag | Mistura fungicida, e, processo para controlar fungos nocivos |
| US6352895B1 (en) * | 2000-03-15 | 2002-03-05 | International Business Machines Corporation | Method of forming merged self-aligned source and ONO capacitor for split gate non-volatile memory |
| FR2812633A1 (fr) * | 2000-08-04 | 2002-02-08 | Aventis Cropscience Sa | Derives de phenyl(thio)urees et phenyl(thio)carbamates fongicides |
| CN107125252A (zh) * | 2017-07-03 | 2017-09-05 | 南京农业大学 | 一种含有氰烯菌酯和克菌丹的杀菌组合物 |
| KR20240132077A (ko) * | 2022-01-12 | 2024-09-02 | 아다마 마켓심 리미티드 | 프탈이미드 살진균제를 함유하는 조합물을 포함하는 살진균제 혼합물 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553771A (en) * | 1948-09-23 | 1951-05-22 | Standard Oil Dev Co | Method of preparing n-trichloromethylthioimides |
| BE494267A (zh) * | 1948-05-18 | |||
| ATE136730T1 (de) * | 1993-09-24 | 1996-05-15 | Basf Ag | Fungizide mischungen |
| EP0741970B1 (en) * | 1993-12-02 | 2002-04-24 | Sumitomo Chemical Company Limited | Bactericidal composition |
| PT738259E (pt) * | 1994-02-04 | 2001-01-31 | Basf Ag | Derivados do acido fenilacetico processo e produtos intermediarios para sua preparacao e agentes que os contem |
| NZ278072A (en) * | 1994-02-04 | 1998-02-26 | Basf Ag | Phenylacetic acid oxime derivatives; biocides |
| DE4421041A1 (de) * | 1994-06-17 | 1995-12-21 | Basf Ag | Fungizide Mischungen |
| DE4423612A1 (de) * | 1994-07-06 | 1996-01-11 | Basf Ag | 2-[(Dihydro)pyrazolyl-3'-oxymethylen]-anilide, Verfahren zu ihrer Herstelung und ihre Verwendung |
| DE4423613A1 (de) * | 1994-07-06 | 1996-01-11 | Basf Ag | 2-[1',2',4'-Triazol-3'yloxymethylen]-anilide, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19528651A1 (de) * | 1995-08-04 | 1997-02-06 | Basf Ag | Hydroximsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel |
| AU6742296A (en) * | 1995-08-17 | 1997-03-12 | Basf Aktiengesellschaft | Fungicidal mixtures of an oxime ether carboxylic acid amide with an n-trichloromethyl thiophthalimide |
-
1997
- 1997-04-03 BR BR9708831A patent/BR9708831A/pt unknown
- 1997-04-03 EA EA199800904A patent/EA000837B1/ru not_active IP Right Cessation
- 1997-04-03 CN CN97194055A patent/CN1216441A/zh active Pending
- 1997-04-03 US US09/171,602 patent/US6083970A/en not_active Expired - Lifetime
- 1997-04-03 PL PL97329504A patent/PL329504A1/xx unknown
- 1997-04-03 CA CA002252534A patent/CA2252534A1/en not_active Abandoned
- 1997-04-03 JP JP53848897A patent/JP3810093B2/ja not_active Expired - Fee Related
- 1997-04-03 NZ NZ332099A patent/NZ332099A/xx unknown
- 1997-04-03 AU AU25081/97A patent/AU732286B2/en not_active Ceased
- 1997-04-03 DK DK97916430T patent/DK0900008T3/da active
- 1997-04-03 IL IL12623397A patent/IL126233A/xx not_active IP Right Cessation
- 1997-04-03 DE DE59707655T patent/DE59707655D1/de not_active Expired - Lifetime
- 1997-04-03 KR KR1019980708549A patent/KR20000065012A/ko not_active Application Discontinuation
- 1997-04-03 CZ CZ983308A patent/CZ330898A3/cs unknown
- 1997-04-03 WO PCT/EP1997/001668 patent/WO1997040672A1/de not_active Application Discontinuation
- 1997-04-03 SK SK1409-98A patent/SK140998A3/sk unknown
- 1997-04-03 EP EP97916430A patent/EP0900008B1/de not_active Expired - Lifetime
- 1997-04-03 AT AT97916430T patent/ATE219882T1/de active
- 1997-04-24 TW TW086105366A patent/TW340034B/zh active
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102696646A (zh) * | 2012-06-29 | 2012-10-03 | 陕西上格之路生物科学有限公司 | 一种含克菌丹的杀菌组合物 |
| CN106857599A (zh) * | 2017-04-27 | 2017-06-20 | 广东广康生化科技股份有限公司 | 一种含有吡唑醚菌酯和灭菌丹的杀菌组合物及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6083970A (en) | 2000-07-04 |
| BR9708831A (pt) | 1999-08-03 |
| NZ332099A (en) | 2000-03-27 |
| AU732286B2 (en) | 2001-04-12 |
| EP0900008B1 (de) | 2002-07-03 |
| EA199800904A1 (ru) | 1999-04-29 |
| EP0900008A1 (de) | 1999-03-10 |
| CO4761032A1 (es) | 1999-04-27 |
| CA2252534A1 (en) | 1997-11-06 |
| IL126233A0 (en) | 1999-05-09 |
| JP3810093B2 (ja) | 2006-08-16 |
| ATE219882T1 (de) | 2002-07-15 |
| DK0900008T3 (da) | 2002-07-22 |
| WO1997040672A1 (de) | 1997-11-06 |
| AR006855A1 (es) | 1999-09-29 |
| DE59707655D1 (de) | 2002-08-08 |
| CZ330898A3 (cs) | 1999-06-16 |
| JP2000509048A (ja) | 2000-07-18 |
| KR20000065012A (ko) | 2000-11-06 |
| PL329504A1 (en) | 1999-03-29 |
| AU2508197A (en) | 1997-11-19 |
| TW340034B (en) | 1998-09-11 |
| IL126233A (en) | 2000-12-06 |
| SK140998A3 (en) | 1999-04-13 |
| EA000837B1 (ru) | 2000-04-24 |
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