CN100345483C - 使植物对细菌病害免疫的方法 - Google Patents
使植物对细菌病害免疫的方法 Download PDFInfo
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- CN100345483C CN100345483C CNB038057417A CN03805741A CN100345483C CN 100345483 C CN100345483 C CN 100345483C CN B038057417 A CNB038057417 A CN B038057417A CN 03805741 A CN03805741 A CN 03805741A CN 100345483 C CN100345483 C CN 100345483C
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Classifications
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- 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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- 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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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Abstract
本发明涉及使植物对细菌病害免疫的方法,其特征在于将植物、土壤或种子用有效量的式I化合物处理,其中:X代表卤素、C1-C4-烷基或三氟甲基;m是0或1;Q代表C(=CH-CH3)-COOCH3、C(=CH-OCH3)-COOCH3、C(=CH-OCH3)-CONHCH3、C(=N-OCH3)-COOCH3、C(=N-OCH3)-CONHCH3或N(-OCH3)-COOCH3;A代表-O-B、-CH2O-B、-CH2S-B、-OCH2-B、-CH=CH-B、-C≡C-B、-CH2O-N=C(R1)-B或-CH2O-N=C(R1)-C(R2)=N-OR3,其中:B代表任选取代的苯基、萘基、含有1至3个N原子和/或1个O或S原子或1或2个O和/或S原子的5元或6元杂芳基或5元或6元杂环基;R1代表氢、氰基、烷基、卤代烷基、环烷基、烷氧基;R2代表任选取代的苯基、苯基羰基、苯基磺酰基、5元或6元杂芳基、5元或6元杂芳基羰基或5元或6元杂芳基磺酰基,或烷基、环烷基、链烯基、链炔基、烷基羰基、链烯基羰基、链炔基羰基、烷基磺酰基或C(=NORα)-ORβ;且R3代表氢、任选取代的烷基、链烯基和链炔基。所述有效量的化合物被植物或种子吸收。
Description
本发明涉及一种使植物对细菌病害免疫的方法,其包括以有效量的式I化合物处理植物、土壤或种子:
其中:
X是卤素、C1-C4-烷基或三氟甲基;
m是0或1;
Q是C(=CH-CH3)-COOCH3、C(=CH-OCH3)-COOCH3、C(=N-OCH3)-CONHCH3、C(=N-OCH3)-COOCH3或N(-OCH3)-COOCH3;
A是-O-B、-CH2O-B、-CH2S-B、-OCH2-B、-CH=CH-B、-C≡C-B、-CH2O-N=C(R1)-B或-CH2O-N=C(R1)-C(R2)=N-OR3,其中
B是苯基、萘基、含有1至3个N原子和/或1个O或S原子或1或2个O和/或S原子的5元或6元杂芳基或5元或6元杂环基,该环系是未取代的或被1至3个基团Ra取代:
Ra是氰基、硝基、氨基、氨基羰基、氨基硫代羰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基羰基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基(sulfoxyl)、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯氧基、苯基、苯氧基、苄基、苄氧基、5或6元杂环基、5或6元杂芳基、5或6元杂芳氧基、C(=NORα)-ORβ或OC(Rα)2-C(Rβ)=NORβ,其中的环状基团又可以是未取代的或被1至3个基团Rb取代:
Rb是氰基、硝基、卤素、氨基、氨基羰基、氨基硫代羰基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯氧基、C3-C6-环烷基、C3-C6-环烯基、苯基、苯氧基、苯硫基、苄基、苄氧基、5或6元杂环基、5或6元杂芳基、5或6元杂芳氧基或C(=NORα)-ORβ;
Rα、Rβ是氢或C1-C6-烷基;
R1是氢、氰基、C1-C4-烷基、C1-C4-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基;
R2是苯基、苯基羰基、苯基磺酰基、5或6元杂芳基、5或6元杂芳基羰基或5或6元杂芳基磺酰基,该环系是未取代的或被1至3个基团Ra取代;
C1-C10-烷基、C3-C6-环烷基、C2-C10-链烯基、C2-C10-链炔基、C1-C10-烷基羰基、C2-C10-链烯基羰基、C3-C10-链炔基羰基、C1-C10-烷基磺酰基或C(Rα)=NORβ,这些基团中的烃基是未取代的或被1至3个基团Rc取代:
Rc是氰基、硝基、氨基、氨基羰基、氨基硫代羰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯氧基,C3-C6-环烷基、C3-C6-环烷氧基、5或6元杂环基、5或6元杂环氧基、苄基、苄氧基、苯基、苯氧基、苯硫基、5或6元杂芳基、5或6元杂芳氧基和杂芳硫基,所述的环状基团又可以是部分或完全卤代的或在其上连接有1至3个基团Ra;且
R3是氢、C1-C6-烷基、C2-C6-链烯基、C2-C6-链炔基,这些基团中的烃基是未取代的或被1至3个基团Rc取代;
该化合物可被植物或种子吸收。此外,本发明还涉及式I化合物用于使植物对细菌病害免疫的用途。
细菌可大量见于温带及湿暖气候地区,作为许多农作物上的疾病病原体(细菌病害)。偶而,这些疾病会造成巨大的经济损失。常见的实例为由各种欧文氏菌(Erwinia)造成的全部水果种植物的死亡(梨子及苹果的“火烧病”)、马铃薯和许多其它植物的细菌软腐病、由农杆菌所引发的各种植物肿瘤、由黄单胞菌(Xanthomonas)于各种蔬菜、稻、小麦和柑橘类水果上所引起的坏死。由假单胞菌(Pseudomonas)特别是于蔬菜、高木性果树(topfruit)及烟草所引起的细菌病害尤其令人担忧。
可预料的是,作用于真菌特异性代谢过程的常规杀真菌剂无法有效地对抗细菌病害。因此,目前可能防治它们的唯一方法是使用抗生素(例如链霉素、杀稻瘟素S或春日霉素),但该方法很少使用:于农业上大量使用抗生素一直为人们所争论,因为这些抗生素大体上是依赖与人用和兽用药对抗细菌病原体的相同的作用机制。因此它们易于产生抗药性。另外,由于其分子结构(大部分十分复杂)且只能用生物技术方法制备,因此抗生素甚为昂贵。
因此开发或模拟植物的固有防御体系构成了一套复杂的理论。
EP-A 420803描述了苯并-1,2,3-噻唑衍生物对抗各种致植物病微生物的免疫效果。WO-A 96/37493公开了吡啶基噻唑的类似效果。但是这些物质的效果常常是不够的。
本发明的目标是提供可广泛使用的方法,该方法不会与用于对抗人类及动物的细菌病害的方法相抵触,为生态上及毒理学上可接受且当产生有效的抗植物细菌病害的免疫作用时不会损伤植物。
我们已发现:该目的可以通过开始时所定义的方法来实现。所用的活性成分已知可以作为抗真菌剂,并且在某些情况下,还可作为杀虫剂(EP-A 178 826;EP-A 253 213;WO-A 93/15046;WO-A 95/18789;WO-A 95/21153;WO-A 95/21154;WO-A 95/24396;WO-A 96/01256;WO-A 97/15552)。但是目前尚未有结果显示对植物的“免疫系统”产生刺激作用,而这可导致对细菌病毒的抗性。
由于式I的活性成分在控制植物疾病所需的浓度下被植物良好耐受,因此可以对外露的植物部分进行处理,亦可对植物繁殖物质、种子及土壤进行处理。
在本发明的方法中,活性成分被植物通过叶面或根部吸收并且分布在整个植物的液体中。
因此,在施用本发明的方法后,不仅可以在直接喷药的植物部分发挥保护作用,而且还增强了整个植物对细菌病害的抵抗力。
在该方法的一个优选实施方案中,将外露的植物部分用活性成分I的制剂处理。
用于本发明方法的活性成分的制备由开始所引用文献中可知。
用于本发明方法中的特别优选的活性成份是那些取代基在任何单独或组合情况下具下列含义的成分:
对于本发明的方法,特别优选的是活性成分I,其中Q是C(=CH-OCH3)-COOCH3、C(=N-OCH3)-COOCH3或N(-OCH3)-COOCH3。
式I中的B优选为苯基、吡啶基、嘧啶基、三唑基及吡唑基。
具体地讲,对于本发明的方法,特别优选式II至VIII的活性成分,其中:
V是OCH3和NHCH3,特别是OCH3,
Y是CH和N,且
T和Z彼此独立地是CH和N。
优选的其中Q是N(-OCH3)-COOCH3的式I的活性成分是公开文献WO-A 93/15046和WO-A 96/01256中记载的化合物。
优选的其中Q是C(=CH-OCH3)-COOCH3的式I的活性成分是公开文献EP-A 178826和EP-A 278595中记载的化合物。
优选的其中Q是C(=N-OCH3)-COOCH3的式I的活性成分是公开文献EP-A 253213和EP-A 254426中记载的化合物。
优选的其中Q是C(=N-OCH3)-CONHCH3的式I的活性成分是公开文献EP-A 398692、EP-A 477631和EP-A 628540中记载的化合物。
优选的其中Q是C(=CH-CH3)-COOCH3的式I的活性成分是公开文献EP-A 280185和EP-A 350691中记载的化合物。
优选的其中A是-CH2O-N=C(R1)-B的式I的活性成分是公开文献EP-A460575和EP-A 463488中记载的化合物。
优选的其中A是-O-B的式I的活性成分是公开文献EP-A 382375和EP-A 398692中记载的化合物。
优选的其中A是-CH2O-N=C(R1)-C(R2)=N-OR3的式I的活性成分是公开文献WO-A 95/18789、WO-A 95/21153、WO-A 95/21154、WO-A 97/05103和WO-A 97/06133中记载的化合物。
特别优选如下的式I的活性成分,其中:
Q是N(-OCH3)-COOCH3,
A是CH2-O-,且
B是3-吡唑基或1,2,4-三唑基,其中B上连接有1或2个选自下列的取代基:
·卤素、甲基和三氟甲基,和
·苯基和吡啶基,特别是2-吡啶基,其被1至3个基团Rb取代。
这些活性成分由式II所表示,
其中Ra′为氯、甲基或三氟甲基,Rb具有式I中所给出的含义,x为1或2,且y为0或1。
特别优选的活性成分还有式II′的化合物,
另外,优选式III的活性成分,
其中V为OCH3或NHCH3,Y为N且Ra为卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基。
特别优选式III的活性成分,其中V为OCH3且Ra为卤素、甲基、二甲基或三氟甲基,特别是甲基。
就其用途而言,特别优选下表中所列的化合物。
表I
编号 | T | (Ra′)y | 苯基-(Rb)x的位置 | (Rb)x | 参考文献 |
I-1 | N | - | 1 | 2,4-Cl2 | WO-A 96/01256 |
I-2 | N | - | 1 | 4-Cl | WO-A 96/01256 |
I-3 | CH | - | 1 | 2-Cl | WO-A 96/01256 |
I-4 | CH | - | 1 | 3-Cl | WO-A 96/01256 |
I-5 | CH | - | 1 | 4-Cl | WO-A 96/01256 |
I-6 | CH | - | 1 | 4-CH3 | WO-A 96/01256 |
I-7 | CH | - | 1 | H | WO-A 96/01256 |
I-8 | CH | - | 1 | 3-CH3 | WO-A 96/01256 |
I-9 | CH | 5-CH3 | 1 | 3-CF3 | WO-A 96/01256 |
I-10 | CH | 1-CH3 | 5 | 3-CF3 | WO-A 99/33812 |
I-11 | CH | 1-CH3 | 5 | 4-Cl | WO-A 99/33812 |
I-12 | CH | 1-CH3 | 5 | - | WO-A 99/33812 |
表II
编号 | V | Y | Ra | 参考文献 |
II-1 | OCH3 | N | 2-CH3 | EP-A 253 213 |
II-2 | OCH3 | N | 2,5-(CH3)2 | EP-A 253 213 |
II-3 | NHCH3 | N | 2,5-(CH3)2 | EP-A 477 631 |
II-4 | NHCH3 | N | 2-Cl | EP-A 477 631 |
II-5 | NHCH3 | N | 2-CH3 | EP-A 477 631 |
II-6 | NHCH3 | N | 2-CH3、4-OCF3 | EP-A 628 540 |
II-7 | NHCH3 | N | 2-Cl、4-OCF3 | EP-A 628 540 |
II-8 | NHCH3 | N | 2-CH3、4-OCH(CH3)-C(CH3)=NOCH3 | EP-A 11 18 609 |
II-9 | NHCH3 | N | 2-Cl、4-OCH(CH3)-C(CH3)=NOCH3 | EP-A 11 18 609 |
II-10 | NHCH3 | N | 2-CH3、4-OCH(CH3)-C(CH2CH3)=NOCH3 | EP-A 11 18 609 |
II-11 | NHCH3 | N | 2-Cl、4-OCH(CH3)-C(CH3)=NOCH2CH3 | EP-A 11 18 609 |
表III
编号 | V | Y | T | Ra | 参考文献 |
III-1 | OCH3 | CH | N | 2-OCH3、4-CF3 | WO-A 96/16047 |
III-2 | OCH3 | CH | N | 2-OCH(CH3)2、4-CF3 | WO-A 96/16047 |
III-3 | OCH3 | CH | CH | 2-CF3 | EP-A 278 595 |
III-4 | OCH3 | CH | CH | 3-CF3 | EP-A 278 595 |
III-5 | NHCH3 | N | CH | 3-Cl | EP-A 398 692 |
III-6 | NHCH3 | N | CH | 3-CF3 | EP-A 398 692 |
III-7 | NHCH3 | N | CH | 3-CF3、5-Cl | EP-A 398 692 |
III-8 | NHCH3 | N | CH | 3-Cl、5-CF3 | EP-A 398 692 |
表IV
编号 | V | Y | R1 | B | 参考文献 |
IV-1 | OCH3 | CH | CH3 | (3-CF3)C6H4 | EP-A 370 629 |
IV-2 | OCH3 | CH | CH3 | (3,5-Cl2)C6H3 | EP-A 370 629 |
IV-3 | NHCH3 | N | CH3 | (3-CF3)C6H4 | WO-A 92/13830 |
IV-4 | NHCH3 | N | CH3 | (3-OCF3)C6H4 | WO-A 92/13830 |
IV-5 | OCH3 | N | CH3 | (3-OCF3)C6H4 | EP-A 460 575 |
IV-6 | OCH3 | N | CH3 | (3-CF3)C6H4 | EP-A 460 575 |
IV-7 | OCH3 | N | CH3 | (3,4-Cl2)C6H3 | EP-A 460 575 |
IV-8 | OCH3 | N | CH3 | (3,5-Cl2)C6H3 | EP-A 463 488 |
表V
编号 | V | R1 | R2 | R3 | 参考文献 |
V-1 | OCH3 | CH3 | CH3 | CH3 | WO-A 95/18789 |
V-2 | OCH3 | CH3 | CH(CH3)2 | CH3 | WO-A 95/18789 |
V-3 | OCH3 | CH3 | CH2CH3 | CH3 | WO-A 95/18789 |
V-4 | NHCH3 | CH3 | CH3 | CH3 | WO-A 95/18789 |
V-5 | NHCH3 | CH3 | 4-F-C6H4 | CH3 | WO-A 95/18789 |
V-6 | NHCH3 | CH3 | 4-Cl-C6H4 | CH3 | WO-A 95/18789 |
V-7 | NHCH3 | CH3 | 2,4-Cl2-C6H3 | CH3 | WO-A 95/18789 |
V-8 | NHCH3 | Cl | 4-F-C6H4 | CH3 | WO-A 98/38857 |
V-9 | NHCH3 | Cl | 4-Cl-C6H4 | CH2CH3 | WO-A 98/38857 |
V-10 | NHCH3 | CH3 | CH2C(=CH2)CH3 | CH3 | WO-A 97/05103 |
V-11 | NHCH3 | CH3 | CH=C(CH3)2 | CH3 | WO-A 97/05103 |
V-12 | NHCH3 | CH3 | CH=C(CH3)2 | CH2CH3 | WO-A 97/05103 |
V-13 | NHCH3 | CH3 | CH=C(CH3)CH2CH3 | CH3 | WO-A 97/05103 |
V-14 | NHCH3 | CH3 | O-CH(CH3)2 | CH3 | WO-A 97/06133 |
V-15 | NHCH3 | CH3 | O-CH2CH(CH3)2 | CH3 | WO-A 97/06133 |
V-16 | NHCH3 | CH3 | C(CH3)=NOCH3 | CH3 | WO-A 97/15552 |
表VI
编号 | V | Y | Ra | 参考文献 |
VI-1 | NHCH3 | N | H | EP-A 398 692 |
VI-2 | NHCH3 | N | 3-CH3 | EP-A 398 692 |
VI-3 | NHCH3 | N | 2-NO2 | EP-A 398 692 |
VI-4 | NHCH3 | N | 4-NO2 | EP-A 398 692 |
VI-5 | NHCH3 | N | 4-Cl | EP-A 398 692 |
VI-6 | NHCH3 | N | 4-Br | EP-A 398 692 |
表VII
编号 | V | Y | T | Ra | 参考文献 |
VII-1 | OCH3 | CH | N | 4-O-(2-CN-C6H4) | EP-A 382 375 |
VII-2 | OCH3 | CH | N | 4-O-(2-Cl-C6H4) | EP-A 382 375 |
VII-3 | OCH3 | CH | N | 4-O-(2-CH3-C6H4) | EP-A 382 375 |
VII-4 | NHCH3 | N | N | 4-O-(2-Cl-C6H4) | GB-A 22 53 624 |
VII-5 | NHCH3 | N | N | 4-O-(2,4-Cl2-C6H3) | GB-A 22 53 624 |
VII-6 | NHCH3 | N | N | 4-O-(2-CH3-C6H4) | GB-A 22 53 624 |
VII-7 | NHCH3 | N | N | 4-O-(2-CH3,3-Cl-C6H3) | GB-A 22 53 624 |
VII-8 | NHCH3 | N | N | 4-O-(2-CH3-C6H4)、5-F | WO-A 98/21189 |
VII-9 | NHCH3 | N | N | 4-O-(2-Cl-C6H4)、5-F | WO-A 98/21189 |
VII-10 | NHCH3 | N | N | 4-O-(2-CH3,3-Cl-C6H3)、5-F | WO-A 98/21189 |
VII-11 | NHCH3 | N | N | 4-O-(2-Cl,3-CH3-C6H3)、5-F | WO-A 98/21189 |
化合物I可以增强植物对细菌病害的抵抗力。它们对于控制各种农作物例如蔬菜、高木性果树种类及烟草以及这些植物的种子上的细菌尤为重要。
具体地讲,它们适于控制如下植物疾病:
在烟草、马铃薯、番茄和豆类中,假单胞菌,以及特别是
在水果、蔬菜及马铃薯中,欧文氏菌。
式III的化合物、特别是化合物II-1,特别适于防治欧文氏菌。
化合物I通过将需要防止细菌感染的植物、种子或土壤用有效量的活性成分处理来施用。施用在细菌感染植物或种子之前进行。由此可观察到植物对细菌病害的易感性显著降低。
对于在农作物保护中的应用,应用比例在每公顷0.01至2.0kg活性成分之间,这取决于病原体的类型和植物的种类。
在处理种子时,每公斤种子通常需要0.001至0.1g、优选0.01至0.05g活性成分。
可将化合物I制成杀真菌剂常用的制剂,例如溶液剂、乳剂、混悬剂、撒粉、粉末、糊剂和颗粒剂。应用形式取决于具体的目的;在任何情况下,均应确保本发明的化合物能够良好并且均匀地分布。
制剂以已知的方式制备,例如,用溶剂和/或载体对活性成分增容,如需要,可使用乳化剂和分散剂,当使用水作为稀释剂时,还可以使用其它有机溶剂作为助溶剂。适宜的辅剂基本上是常用于杀真菌剂的那些。
通常,制剂含有0.01至95重量%、优选0.1至90重量%的活性成分。所用活性成分的纯度为90%至100%、优选95%至100%(根据NMR波谱确定)。
以下是制剂的实例:
I.将5重量份本发明的化合物与95重量份细粉状的高岭土紧密混合。由此得到合有5重量%活性成分的撒粉。
II.将30重量份本发明的化合物与92重量份粉状硅胶和8重量份石蜡油的混合物混合,其中,所述的石蜡油已被喷雾在所述硅胶的表面。由此得到具有良好粘附特性的活性成分的制剂(活性成分含量23重量%)。
III.将10重量份本发明的化合物溶于由90重量份二甲苯、6重量份8至10mol环氧乙烷和1mol油酸N-一乙醇酰胺的加合物、2重量份十二烷基苯磺酸钙和2重量份40mol环氧乙烷和1mol蓖麻油的加合物组成的混合物(活性成分含量9重量%)。
IV.将20重量份本发明的化合物溶于由60重量份环己酮、30重量份异丁醇、5重量份7mol环氧乙烷和1mol异辛基苯酚的加合物和5重量份40mol环氧乙烷和1mol蓖麻油的加合物组成的混合物(活性成分含量16重量%)。
V.将80重量份本发明的化合物与3重量份二异丁基萘-α-磺酸钠、10重量份来自亚硫酸盐废液的木质素磺酸的钠盐和7重量份粉状的硅胶充分混合,然后将混合物在锤磨机中研磨(活性成分含量80重量%)。
VI.将90重量份本发明的化合物与10重量份N-甲基-α-吡咯烷酮混合,由此得到适于以微滴的形式使用的溶液(活性成分含量90重量%)。
VII.将20重量份本发明的化合物溶于由40重量份环己酮、30重量份异丁醇、20重量份7mol环氧乙烷和1mol异辛基苯酚的加合物和10重量份40mol环氧乙烷和1mol蓖麻油的加合物组成的混合物。将该溶液倒入100000重量份的水中并将其均匀地分散在其中,得到含有0.02重量%活性成分的含水分散液。
VIII.将20重量份本发明的化合物与3重量份二异丁基萘-α-磺酸钠、17重量份自亚硫酸盐废液的木质素磺酸的钠盐和60重量份粉状的硅胶充分混合,然后将混合物在锤磨机中研磨。将该混合物均匀地分散在20000重量份的水中,得到含有0.1重量%活性成分的喷雾混合物。
含水的使用形式可以按照常规方式通过加入水从乳液浓缩物、糊剂或可湿性粉末(可喷雾的粉末、油分散液)制备。为了制备乳液、糊剂和油分散液,可将物质本身或溶于油或溶剂中的物质用湿润剂、粘合剂、分散剂或乳化剂在水中均质化。或者,可以制备由活性物质、湿润剂、粘合剂、分散剂或乳剂以及,如果合适的话,溶剂或油组成的浓缩物,这些浓缩物适于用水进行稀释。
即可使用的制剂中的活性成分浓度可以在较宽的范围内变化。通常,它们可以在0.0001至10%之间,优选在0.01至1%之间。
活性成分还可以成功地用于极微量(ULV)法,可以使用含有95重量%以上活性成分的制剂,甚至可以使用不含添加剂的活性成分。
如果合适的话,还可以在临用前向活性成分中加入各种类型的油、除草剂、其它杀真菌剂、其它杀虫剂、抗菌剂(罐混合)。可将这些试剂与本发明的试剂以重量比1∶10至10∶1进行混合。
活性成分I诱发细菌抗性的效果可以以标签的形式存在于包装上或产品资料单内。该说明还可以存在于可与活性成分I联合使用的制剂箱内。
诱导抵抗力也可以构成官方批准活性成分I的一种适应症。
用如下实验证实通式I化合物的作用:
诱发细菌抗性的用途实施例
植物材料
为了进行实验,使烟草植物(Nicotiana tabacum cv.Xanthi-nc)在25℃、大气湿度59%和日光照时间16小时(150-200μM量子/s-1/m-2)的条件下在罐装堆肥(标准土壤型ED 73)中生长6至8周。每周一次通过向浇灌水中加入推荐比例的市售家养植物肥料(10%总氮、9%磷酸盐、7%钾碱)对部分植物施肥。
施用活性成分
活性成分以0.1mM水溶液形式(以1%v/v二甲基亚砜[DMSO]制备的稀释液)喷雾在植物上或借助极细的插管直接渗入叶片组织中。对照组植物以不含活性成分的溶液按照类似的方法处理。为使生物学差异的影响减到最低,部分实验涉及于每一情况下以活性成分的溶液处理叶片的一半(中央叶脉的左边或右边),同一叶子的另外一半以对照溶液处理。
施用活性成分后以及在以丁香假单胞菌(Pseudomonas syringae)接种后,将植物置于生长室内。
接种/感染和抗性的确定
将如上所述已施用了活性成分的烟草植物或叶片用丁香假单胞菌番茄致病型(Pseudomonas syringae pv.tomato,DC3000株,来源:加州大学柏克莱分校的Brian Staskawicz)或丁香假单胞菌烟草致病型(Pseudomonassyringae pv.tabaci)(德国微生物与细胞培养物保存中心,Brunswick,德国)感染。为此,使细菌在30℃下于King′s培养基中生长一天,离心,洗涤,并使其在10mM MgCl2溶液中的密度为105cfu/ml。将约200μl该接种物(2×104cfu/ml)经由插管在叶片上所致的小划痕直接渗入叶片组织中。
在随后的一星期中,以叶坏死的程度作为感染的结果加以确定。没有坏死症状是叶片组织的抗性被诱发的特征。
细菌生长的确定
为了定量细菌的数目,自感染的叶片区域打两个孔(φ1cm),得到两个一组的各组叶节,并于500μL无菌水中均化。将该稀释序列接种于King′s B琼脂中,并于30℃下培育两天后,基于所形成的菌落数计算每个叶盘的起始菌数浓度(cfu)。
应用实施例
用活性成分I-5处理后,烟草叶对丁香假单胞菌番茄致病型DC3000的抗性增加(不相容的相互作用)且由丁香假单胞菌烟草致病型所造成的疾病症状的产生减少(相容的相互作用)。
实施例1:对丁香假单胞菌烟草致病型的免疫作用(相容的相互作用)
在相容的宿主-病原体组合的情况下,(接种前24至48小时)应用≤0.01%强度的活性成分I-5的制剂抑制了细菌的生长并减少了疾病症状的显现。
在存在或不存在活性成分I-5时用菌落接种King′s B培养基后,丁香假单胞菌烟草致病型的生长动力学进程证明:活性成分自身在体外对细菌的生长并无影响。
因此所观察的作用是基于对植物对病原体的固有防御或抗性的刺激。
表A.丁香假单胞菌烟草致病型在接种烟草叶片中的生长
时间(小时) | 细菌(×106细胞/ml(叶盘-1) | |
活性成分I-5 | 对照组 | |
0 | 0 | 0 |
16 | 0.3 | 0.3 |
24 | 1.2 | 3.3 |
48 | 1.4 | 3.7 |
实施例2:对丁香假单胞菌番茄致病型DC3000的免疫作用(不相容的相互作用)
即使在不相容的相互作用的情况下,疾病症状的显现亦大大地减少(即植物本身迅速地通过形成坏死(“防御”)而对已渗入的病原体有所响应,但是这种情况也包括感染组织区域的死亡)。
表B:用丁香假单胞菌番茄致病型DC3000接种叶脉区域后,烟草叶片中的感染进程
时间(小时) | 叶片的改变(叶脉区域面积%) | |||
活性成分I-5 | 对照组 | |||
萎凋症状 | 坏死 | 萎凋症状 | 坏死 | |
0 | 0 | 0 | 0 | 0 |
24 | 0 | 0 | 100 | 0 |
48 | 0 | 5 | - | 100 |
72 | 0 | 8 | - | 100 |
144 | 0 | 15 | - | 100 |
168 | 0 | 20 | - | 100 |
施用活性成分I-5的制剂后,少数显现坏死的区域直接局限于接种部位,在那里叶片被划开。24小时后,对照组植物的叶片已萎凋,且于48小时后全部死亡。
Claims (7)
1.使植物对细菌病害免疫的方法,其包括将植物、土壤或种子用有效量的式I化合物处理,
其中:
X是卤素、C1-C4-烷基或三氟甲基;
m是0;
Q是C(=CH-CH3)-COOCH3、C(=CH-OCH3)-COOCH3、C(=N-OCH3)-CONHCH3、C(=N-OCH3)-COOCH3或N(-OCH3)-COOCH3;
A是-O-B、-CH2O-B、-CH2O-N=C(R1)-B或-CH2O-N=C(R1)-C(R2)=N-OR3,其中
B是苯基、吡啶基、嘧啶基、吡唑基、三唑基,这些环系被1或2个基团Ra取代:
Ra是氰基、硝基、氨基、氨基羰基、氨基硫代羰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基羰基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯氧基、苯基、苯氧基、苄基、苄氧基、5或6元杂环基、5或6元杂芳基、5或6元杂芳氧基、C(=NORα)-ORβ或OC(Rα)2-C(Rβ)=NORβ,
其中的环状基团又可以是未取代的或被1至3个基团Rb取代:
Rb是氰基、硝基、卤素、氨基、氨基羰基、氨基硫代羰基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧基羰基、C1-C6-烷硫基、C1-C6-烷基氨基、二-C1-C6-烷基氨基、C1-C6-烷基氨基羰基、二-C1-C6-烷基氨基羰基、C1-C6-烷基氨基硫代羰基、二-C1-C6-烷基氨基硫代羰基、C2-C6-链烯基、C2-C6-链烯氧基、C3-C6-环烷基、C3-C6-环烯基、苯基、苯氧基、苯硫基、苄基、苄氧基、5或6元杂环基、5或6元杂芳基、5或6元杂芳氧基或C(=NORα)-ORβ;
Rα、Rβ是氢或C1-C6-烷基;
R1是氢、氰基、C1-C4-烷基、C1-C4-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基;
R2是C1-C6-烷基、C2-C10-链烯基、C3-C6-环烷基,这些基团是未取代的或被1或2个基团Rb’取代;
Rb’是C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、苄基、苯基或苯氧基;
或未取代的或被1或2个基团Ra取代的苯基;
R3是C1-C6-烷基、C2-C10-链烯基或C2-C10-链炔基;该化合物可被植物或种子吸收。
2.如权利要求1所述的方法,其中使用式II的活性成分,
其中T为CH或氮原子,Ra′为氯、甲基或三氟甲基,Rb具有式I中所给出的含义,且x为1或2,y为0或1。
3.根据权利要求1的方法,其中使用式III的活性成分,
其中V为OCH3,Y为N且Ra为甲基、二甲基或卤素。
4.权利要求1至3中任一项所述的方法,其用于抗欧文氏菌免疫。
5.权利要求1至3中任一项所述的方法,其中对植物进行处理。
6.权利要求1至3中任一项所述的方法,其中对种子进行处理。
7.权利要求1至3中任一项所述的式I、II或III化合物用于使植物对细菌病害免疫的用途。
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CA2698293A1 (en) | 2007-09-13 | 2009-03-26 | Thomas Subkowski | Use of hydrophobin polypeptides as penetration intensifiers |
CA2707814C (en) * | 2007-12-21 | 2012-10-02 | Basf Se | Method for increasing the milk of milk producing animals fed with silage obtained from plants treated with a strobilurin compound |
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JP2013500297A (ja) | 2009-07-28 | 2013-01-07 | ビーエーエスエフ ソシエタス・ヨーロピア | 多年生植物の貯蔵組織における遊離アミノ酸レベルを増大させる方法 |
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CN102741327B (zh) | 2010-02-05 | 2014-11-05 | 巴斯夫欧洲公司 | 在水溶液中加溶疏水性活性成分的方法 |
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CA2800369C (en) | 2010-05-31 | 2018-07-10 | Basf Se | Method for increasing the health of a plant |
EP2654427B1 (en) | 2010-12-22 | 2014-09-24 | Basf Se | Agrochemical mixtures for increasing the health of a plant |
EP3378313A1 (en) | 2011-03-23 | 2018-09-26 | Basf Se | Compositions containing polymeric, ionic compounds comprising imidazolium groups |
EP3050919A1 (de) | 2015-01-29 | 2016-08-03 | Basf Se | Lignocellulosehaltige materialen enthaltend mischungen mit salzen von n-substituierten carbamidsäuren |
WO2023111297A1 (en) | 2021-12-17 | 2023-06-22 | Basf Se | Lactones for enhancing the activity of antimicrobial agents |
WO2023111296A1 (en) | 2021-12-17 | 2023-06-22 | Basf Se | Composition comprising an antimicrobial agent and a carboxamide |
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ATE275551T1 (de) * | 1999-06-18 | 2004-09-15 | Bayer Cropscience Ag | Halogenpyrimidine |
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PL372938A1 (en) | 2005-08-08 |
EA200401131A1 (ru) | 2005-02-24 |
CA2478591C (en) | 2012-01-03 |
AU2003212325B8 (en) | 2003-09-22 |
TW200408350A (en) | 2004-06-01 |
EP1484973B1 (de) | 2012-05-09 |
BR0308325B1 (pt) | 2014-10-07 |
WO2003075663A1 (de) | 2003-09-18 |
EP1484973A1 (de) | 2004-12-15 |
CN1642424A (zh) | 2005-07-20 |
CA2478591A1 (en) | 2003-09-18 |
TWI349525B (en) | 2011-10-01 |
BR0308325A (pt) | 2004-12-28 |
BR0308325A8 (pt) | 2018-03-20 |
AU2003212325B2 (en) | 2007-08-23 |
EA012135B1 (ru) | 2009-08-28 |
MXPA04008043A (es) | 2004-11-26 |
PL211515B1 (pl) | 2012-05-31 |
AU2003212325A1 (en) | 2003-09-22 |
NZ534978A (en) | 2006-03-31 |
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