CN1226242A - 二氢呋喃-羧酰胺 - Google Patents
二氢呋喃-羧酰胺 Download PDFInfo
- Publication number
- CN1226242A CN1226242A CN97196706A CN97196706A CN1226242A CN 1226242 A CN1226242 A CN 1226242A CN 97196706 A CN97196706 A CN 97196706A CN 97196706 A CN97196706 A CN 97196706A CN 1226242 A CN1226242 A CN 1226242A
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- carbon atom
- alkyl
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- cycloalkyl
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明涉及具有通式(Ⅰ)的二氢呋喃—羧酰胺,其中R表示具有通式(a)(b)或(c)的基团,式中R1、R2、R3、X、m、n和p具有在说明书中的定义。本发明还涉及制备该新型物质的方法及其作为用于植物和材料保护目的抗击不需要的细菌的运用。
Description
本发明涉及新型二氢呋喃-羧酰胺、涉及其制备方法及其作为杀菌剂的用途。
人们已经知道某些二氢呋喃N-羧酰苯胺具有杀真菌性能(参见DE-A1914954和J,Pesticide Sci.18(1993),245-251),因此举例来说,可以采用2-甲基-4,5-二氢呋喃-3-羧酰苯胺和2-甲基-4,5-二氢-3-N-(1,1,3-三甲基二氢化茚-4-基)羧酰胺-来控制真菌。这些化合物的活性是良好的,但是在低剂量的情况下,还有不足。
R1代表任意取代的环烷基、任意取代的双环烷基、任意取代的环链烯基、任意取代的环烷基烷基、任意取代的芳基、任意取代的芳氧基、任意取代的芳烷基或代表烷基,
X代表具有1-6个碳原子的烷基、卤素、具有3-8个碳原子的环烷基、具有1-6个碳原子的烷氧基、具有1-4个碳原子和1-5个卤素原子的卤代烷基或具有1-4个碳原子和1-5个卤素原子的卤代烷氧基,
m表示0-3的整数,
R2代表烷基、环烷基、任意取代的芳基或任意取代的芳烷基,
n表示0-3的整数,
R3表示烷基、环烷基,任意取代的芳基或任意取代的芳烷基以及
p表示0-3的整数。
此外,已经发现当在一种酸粘合剂的适当存在下以及在一种稀释剂的适当存在下将具有下列通式(Ⅱ)的2-甲基-4,5-二氢呋喃-3-碳酰卤与具有通式(Ⅲ)的胺起反应时,可以获得具有通式(Ⅰ)的二氢呋喃-羧酰胺式中Hal表示氯或溴,
H2N-R (Ⅲ)式中R如上所定义。
最后,已经发现具有通式(Ⅰ)的新型二氢呋喃-羧酰胺具有非常好的杀菌性能并且可以在农作物保护和材料保护过程中用于控制不需要的微生物。
出乎人们意料的是,本发明的二氢呋喃-羧酰胺具有比2-甲基-4,5-二氢呋喃-3-羧酰苯胺和2-甲基-4,5-二氢呋喃-3-N-(1,1,3-三甲基二氢化茚-4-基)-羧酰胺更好的杀真菌活性,后两种化合物是具有相同作用方向的在组成上相类似的现有的活性化合物。
通式(Ⅰ)提供了本发明的二氢呋喃-羧酰胺的一般定义。R优选地代表具有下列通式的基团:式中
R1优选地代表具有3-8个碳原子的环烷基,该基团任选地被相同的或不同的具有1-4个碳原子的烷基基团单取代或三取代,代表具有7-12个碳原子的双环烷基,该基团任选地被相同的和不同的具有1-4个碳原子的烷基基团单取代或三取代,代表5-8个碳原子的环链烯基,该基团任选地被相同的或不同的具有1-4个碳原子的烷基基团单取代或三取代,或者代表在环烷基部分具有3-8个碳原子和在烷基部分具有1-4个碳原子的环烷基烷基,该基团任选地被相同的或不同的具有1-4个碳原子的烷基基团单取代或三取代,或者
代表苯基,该苯基可以被相同的或不同的取代基单或三取代,所说的取代基选自卤素和具有1-4个碳原子的烷基,或者
代表苯氧基,该苯氧基可以被相同的或不同的取代基单或三取代,所说的取代基选自卤素和具有1-4个碳原子的烷基,或者
代表在烷基部分具有1-4个碳原子的苯烷基,该苯烷基在苯基部分可以被相同的或不同的取代基单或三取代,所说的取代基选自卤素和具有1-4个碳原子的烷基,
或者代表具有1-12个碳原子的直链或支链烷基,
X优选地代表具有1-4个碳原子的直链或支链烷基、氟、氯、溴、具有3-8个碳原子的环烷基、具有1-4个碳原子的直链或支链烷氧基、具有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基或代表具有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基,
m优选地表示0、1或2,
R2优选地代表具有1-12个碳原子的直链或支链烷基、具有3-8个碳原子的环烷基、苯基,该苯基任选地被相同的或不同的选自卤素和具有1-4个碳原子的取代基单取代或三取代,或者代表在烷基部分具有1-4个碳原子的苯烷基,该苯烷基任选地被相同的或不同的选自卤素和具有1-4个碳原子的烷基的取代基单或三取代,
n优选地表示0、1、2或3,
R3优选地代表具有1-12个碳原子的直链或支链烷基,具有3-8个碳原子的环烷基,苯基,该苯基任选地被相同的或不同的选自卤素和具有1-4个碳原子的取代基单取代或三取代,或者代表在烷基部分具有1-4个碳原子的苯烷基,该苯烷基任选地被相同的或不同的选自卤素和具有1-4个碳原子的烷基的取代基单或三取代以及
p优选地表示0、1、2或3。
特别优选的是下列具有通式(Ⅰ)的二氢呋喃-羧酰胺,其中
R1代表具有3-8个碳原子的环烷基,该基团任选地被相同的或不同的选自甲基、乙基、正丙基、异丙基和叔丁基的取代基单取代或三取代,或者代表具有7-12个碳原子的双环烷基,该基团任选地被相同的和不同的选自甲基、乙基、正丙基、异丙基和叔丁基的取代基单取代或三取代,或
代表5-8个碳原子的环链烯基,该基团任选地被相同的或不同的选自甲基、乙基、正丙基、异丙基和叔丁基的取代基单取代或三取代,或者代表在环烷基部分具有3-8个碳原子和在烷基部分具有1或2个碳原子的环烷基烷基,该基团任选地被相同的或不同的选自甲基、乙基、正丙基、异丙基和叔丁基的取代基单取代或三取代,或者
代表苯基,该苯基可以被相同的或不同的取代基单或三取代,所说的取代基选自氟、氯、溴、甲基、乙基、正丙基、异丙基和叔丁基或者
代表苯氧基,该苯氧基可以被相同的或不同的取代基单或三取代,所说的取代基选自氟、氯、溴、甲基、乙基、正丙基、异丙基和叔丁基,或者
代表在烷基部分具有1或2个碳原子的苯烷基,该苯烷基在苯基部分可以被相同的或不同的取代基单或三取代,所说的取代基选自氟、氯、溴、甲基、乙基、正丙基、异丙基和叔丁基
或者代表具有1-12个碳原子的直链或支链烷基,
X代表甲基、乙基、正丙基、异丙基和叔丁基、氟、氯、溴、环丙基、环戊基、环己基、环庚基、环辛基、甲氧基、乙氧基、三氯甲基、三氟甲基、二氟甲基、二氟氯甲基、三氟甲氧基或二氟甲氧基,
m优选地表示0、1或2,如果m表示2,则X代表相同的或不同的基团,
R2代表选自甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、辛基、癸基、十二烷基、环丙基、环戊基、环己基、环庚基、环辛基、苯基,该苯基任选地被氟、氯、溴、甲基、乙基、正丙基、异丙基和/叔丁基单取代或二次取代,或者代表在烷基部分具有1-2个碳原子的苯烷基,该苯烷基的苯基部分任选地被氟、氯、溴、甲基、乙基、正丙基、异丙基和/叔丁基单或二次取代,
n表示0、1、2或3,如果n表示2或3,则R2代表相同的或不同的基团,
R3代表甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、辛基、癸基、十二烷基、环丙基、环戊基、环己基、环庚基、环辛基、苯基,该苯基任选地被氟、氯、溴、甲基、乙基、正丙基、异丙基和/叔丁基单取代或二次取代,或者在其烷基部分具有1或2个碳原子的苯烷基,该苯烷基的苯基部分任选地被氟、氯、溴、甲基、乙基、正丙基、异丙基和/叔丁基单或二次取代,以及
p表示0、1、2或3,如果p表示2或3,则R3代表相同或不同的基团。
通式(Ⅱ)提供了2-甲基-4,5-二氢呋喃-3-碳酰卤的一般定义,该化合物用作进行本发明的工艺的原料。Hal优选地代表氯或溴。
2-甲基-4,5-二氢呋喃-3-碳酰卤是已经的或者可以通过已知的方法制得(参见DE-A1914954和Chem.Ber.104(1971),734-738)。
通式(Ⅲ)提供了用作进行本发明的工艺的反应成分的胺类一般定义。在该通式中,R优选地具有针对本发明的通式(Ⅰ)的化合物的描述已经提到的优选的基团的定义。
通式(Ⅲ)的胺类是已知的或者可以通过已知的方法制得(参见US-A5223526、EP-A0545099、EP-A0589301和DE-A4445545)。
用于进行本发明的工艺的合适酸粘合剂是通常用于这类反应的所有有机和无机碱。优选的是采用碱土金属或碱金属氢氧化物,如氢氧化钠、氢氧化钙、氢氧化钾或氢氧化铵、碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠、碱金属或碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙,还有叔胺类,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮环辛烷(DABCO)、二氮二环壬烯(DBN)或二氮二环十一碳烯(DBU)。但是,也可以不加入另外的酸粘合剂进行该反应,或者采用过量的胺成分,从而将其同时作为酸粘合剂。
用于进行本发明的工艺的合适稀释剂是所有常用的惰性有机溶剂,优选的是采用任意卤化的脂肪族、脂环族或芳香族烃类,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,如二乙醚、二异丙醚、甲基-叔丁醚、甲基叔戊醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈类,如乙腈、丙腈、正或异丁腈或苄腈;酰胺类,如N,N-二甲基甲酰胺、N-N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷三酰胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜或砜类,如环丁砜。
当进行本发明的工艺时,反应温度可以在较宽的温度范围内变化,一般说来,该反应是在0-100℃,优选地在10-80℃之间的温度下进行。
本发明的工艺通常是在大气压力下进行,但是也可以在升高的压力或降压下进行。
当进行本发明的工艺时,通常每摩尔通式(Ⅱ)的2-甲基-4,5-二氢呋喃-3-碳酰卤采用1摩尔或过量的通式(Ⅲ)的胺和1-3摩尔酸粘合剂。但是也可以以其它的比例采用反应成分。采用常规的方法进行操作。通常是将反应混合物与水混合并且分离出有机相,干燥以后,在降压下浓缩。如果需要,采用常规的方法,如色谱法或重结晶法去除残余杂质。
本发明的化合物具有潜在的杀菌活性并且可以在农作物保护和材料保护过程中用于控制不需要的微生物,如真菌和细菌。
可以采用杀真菌剂来保护农作物,以控制疟原虫、Oomycetes、壶菌、接合菌、子囊菌、担子菌和半知菌。
可以采用杀菌剂来保护农作物,以控制假单胞菌、根瘤菌、肠杆菌、棒状杆菌和链霉菌。
作为例子可以举出引起上述常规名称的真菌和细菌疾病的某些病原体,但不是为了进行限制:
黄单胞菌类,如野油菜及水稻黄单胞菌;
假单胞菌类,如丁香假单胞菌及异型丁香假单胞菌;
欧文氏菌类,如解淀粉欧文氏菌;
腐霉菌类,如最终腐霉菌;
疫霉菌类,如传染性疫霉菌;
假斜尖状孢子类,如律草假斜尖状孢子或古巴假斜尖状孢子;
霜霉菌类,如蔓荆霜霉菌;
盘梗霉菌类,如莴苣盘梗霉菌;
斜尖状孢子类,如豌豆斜尖状孢子或芸苔斜尖状孢子;
丹毒丝菌类,如裸麦丹毒丝菌;
单丝壳菌类,如煤烟状单丝壳菌;
叉丝单囊壳菌类,白发叉丝单囊壳菌;
球腔菌类,如萍果球腔菌;
核球壳菌类,如圆核球壳菌或草核球壳菌;
(分生孢子形式:Drechslera,合成:Helminthosporium);
旋孢菌类,如洒剔(sativus)旋孢菌;
尿霉菌类,如阑尾尿霉菌;
美州血根菌类,如recondita美州血根菌;
子囊菌类,如麦角子囊菌;
腥黑粉菌类,如龋齿腥黑粉菌;
黑粉菌类,如虚有黑粉菌或燕麦黑粉菌;
薄膜革菌类,如sasakii薄膜革菌;
Pyricularia类,如Pyricularia oryzac;
新月孢子菌类,如culmorum新月孢子菌;
葡萄孢子菌类,如灰质葡萄孢子菌;
壳针孢子菌类,如nodorum壳针孢子菌;
小球腔菌类,如nodorum小球腔菌;
孢子菌类,如发白孢子菌;
鞭毛孢子菌类,如芸苔鞭毛孢子菌;
假鞭毛孢子菌类,如毛发状假鞭毛孢子菌。
这些活性化合物在控制植物疾病所需的浓度下可以被植物很好地接受使得我们可以对植物的气生部分、传播树杆和种子以及土壤进行处理。
本发明的活性化合物可以特别成功地用于控制水果和蔬菜生长以及葡萄栽培的疾病,例如控制文丘里菌、足球果菌、疫霉菌和单轴霉菌类。它们还可以非常成功地用于控制稻谷疾病,如Pyricularia菌类。
在材料保护中,本发明的化合物可以用于保护工业材料,以防止受到不合适的细菌的感染和破坏。
本发明中的工业材料可以理解成已经准备用于工业中的无生命材料。举例来说,可以采用本发明的活性材料来保护以防止细菌变化或破坏的工业材料可以是粘结剂、上浆剂、纸和纸板、织物、皮革、木材、涂料和塑料制品、冷却润滑剂和其它可以被细菌感染或破坏的材料。由于微生物的繁殖而受到破坏的生产装置的部件,如冷却水路也属于所要保护的材料范围。在本发明的范围内可以提出的工业材料优选地是粘接剂、上浆剂、纸和纸板、皮革、木材、涂料、冷却润滑剂和传热液体,特别优选的是木材。
可以提出的能够使工业材料降解或改变的微生物例如是细菌、真菌、酵母、藻类和泥土生物。本发明的活性化合物优选地可以对真菌起作用,特别是霉菌、使木材脱色和破坏木材的真菌(担子菌)以及对泥土生物和藻类。
作为例子可以提出下列微生物:
链格孢子菌,如细链格孢子菌,
曲霉菌,如黑曲霉菌,
黑毛菌,如球形黑毛菌,
粉孢革菌,如地窖粉孢革菌,
褶孔层菌,如虎纹褶孔层菌,
青霉菌,如蓝绿色青霉菌,
多孔菌,如杂色多孔菌,
金担子,如污染金担子,
Sclerophoma,如Sclerophoma pityophila,
木霉菌,如绿色木霉菌,
埃希氏杆菌,如大肠杆菌,
假单胞菌,如铜绿假单胞菌,
葡萄球菌,如金色葡萄球菌。
根据它们的特定物理和/或化学性能,这些活性化合物可以转变成常规的配方,如溶液、乳液、悬浮液、粉末、泡沫、浆料、颗粒、气溶胶和用于种子、ULV冷和暖雾配方的在聚合物和涂覆组合物中的微胶囊。
这些配方可以以已知的方式制成,例如通过将活性化合物与补充剂混合,该补充剂是液体溶剂、加压液化气体和/或固体载体,任选地可以采用表面活性剂,该表面活性剂是乳化剂和/或分散剂和/或泡沫形成剂。在采用水作为补充剂的情况下,例如还可以采用有机溶剂作为辅助溶剂。下列物质是适合作为液体溶剂的主要物质:芳香族,如二甲苯、甲苯或烷基萘,氯代芳香族或氯代脂肪烃类,如氯苯、氯乙烯或二氯甲烷,脂肪烃类,如环己烷或石蜡,如石油馏份,醇类,如丁醇和亚醇以及它们的醚类和酯类,酮类,如丙酮、甲乙酮、甲异丁酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,或水。液化的气体补充剂或载体可以理解为在标准温度和大气压下是气态的液体,如气溶胶推进剂,如乳代烃类,或者丁烷、丙烷、氮气和二氧化碳。合适的固体载体例如是模细的天然矿物,如高岭土、粘土、滑石、白垩、石英、活性粘土、蒙脱石或硅藻土和磨细的合成矿物,如高分散石英、氧化铝和硅酸盐。用于颗粒的合适固体载体例如是破碎并分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石、或者无机和有机粉料的合成颗粒,以及无机材料的颗粒,如锯屑、椰子壳、玉米块和红薯茎。合适的乳化剂和/或泡沫形成剂例如是非离子和阳离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,如烷基芳基聚乙二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯或者蛋白质水解物。合适的分散剂例如是木质素-亚硫酸盐废液和甲基纤维素。
在这些配方中可以采用粘接剂,如羧甲基纤维素和天然与合成的聚合物,它们可以是粉末、颗粒或胶乳,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,或天然磷脂,如脑磷脂和卵磷脂,以及合成的磷酯。其它的添加剂可以是矿物或蔬菜油。
可以采用差色剂,如无机颜料,如氧化铁、氧化钛和普鲁士蓝,以及有机染料,如茜数染料、偶氮染料、和金属酞菁染料,和极少量营养成分,如铁、锰、硼、铜、钴、钼和锌的盐。
这些配方通常由0.1-95%重量活性化合物,优选地为0.5-90%重量活性化合物组成。
本发明的活性化合物可以这样使用,也可以在它们与已知的杀真菌剂、杀菌剂、杀螨剂、杀线虫剂或杀虫剂混合的配方中使用,从而扩大作用范围或者防止抗性的形成。在多种情况下,可以获得协同作用,即混合物的活性超过单一组分的活性。
在混合物中的辅助成的例子是下列化合物:杀真菌剂:aldimorph,ampropylfos,ampropylfos钾,andoprim,防霉灵,戊环唑,azoxystrobin,benalaxyl,委锈灵,苯菌灵,benzamacril,benzamacril-异丁基,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,杀稻瘟菌素-S,糠菌唑,磺嘧菌灵,粉病啶,聚硫化钙,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,香芹酮,醌甲二磺酸酯,chlobenthiazone,chlorfenazole,地茂散,氯化苦,百菌清,乙菌利,clozylacon,硫杂灵,cymoxanil,环唑醇,cyprodinil,cyprofuram,debacarb,二氯芬,苄氯三唑醇,diclofluanid,哒菌清,2,6-二氯-4-硝基苯胺,乙霉威,恶醚唑,甲菌定,烯酰吗啉,烯唑醇,速得利-M,消螨普,二苯胺,灭菌磷,二硫二氰蒽醌,吗菌灵,多果定,敌菌酮,敌瘟磷,epoxiconazole,etaconazole,乙菌定,氯唑灵,famoxadon,菌拿灵,异嘧菌醇,fenbuconazole,呋菌胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,氢氧化三苯锡,福美铁,嘧菌腙,氟啶胺,flumetover,,fluoromide,fluquinconazole,调嘧醇,氟硅唑,氟硫酰胺,氟纹胺,粉唑醇,灭菌丹,fosetyl-铝,fosetyl-钠,氯百杀,呋喃基苯并咪唑,呋氨丙灵,furametpyr,呋喃甲酰苯胺,呋菌唑,furconazole-顺式,furmecyclox,双胍辛醋酸盐,六氯苯,己唑醇,土菌消,烯菌灵,酰胺唑,iminoctadine iminoctadine albesilate,双胍辛三醋酸盐,iodocarb,ipconazole,iprobenfos(IBP),异丙二酮,irumamycin,稻瘟灵,isoyaledione,春日霉素,kresoxim-甲基,铜制剂,如氢氧化铜,奈酸铜,氯氧化铜,硫酸铜,氧化铜,oxine-铜和波尔多混合物,代森锰铜,代森锰锌,代森锰,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,metomeclam,metsulfovax,灭粉霉素,腈菌唑,myclozolin,二甲基二硫氨基甲酸镍,nitrothal-异丙基,氟苯嘧啶醇,甲呋酰胺,恶霜灵,oxamocarb,喹酸,萎锈散,oxyfenthiin,多效唑,稻瘟酯,戊菌唑,戊菌隆,phosdiphen,多马徽素,粉病灵,多氧菌素,polyoxorim,烯丙异噻唑,丙氨灵,杀菌利,百维灵,propanosine-钠,丙环唑,甲基代森锌,定菌磷,啶斑肟,pyrimethanil,咯喹酮,pyroxyfur,quinconazole,五氯硝基苯(PCNB),硫和硫制剂,戊唑醇,叶枯酞,四氧硝基苯,tetcyclacis,氟醚唑,噻苯达唑,噻菌腈,thifluzamide,甲基托布津,福美双,tioxymid,甲基立枯磷,tolylfluanid,三唑酮,唑菌醇,triazbutil,唑菌嗪,扬菌胺,三环唑,十三吗啉,氟菌唑,嗪胺灵,triticonazole,烯效唑,有效霉素A,烯菌酮,viniconazole,zarilamide,亚乙基双二硫代氨基甲酸锌,二甲基二硫代氨基甲酸锌和Dagger G,OK-8705,OK-8801,2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-羧酰苯胺,2,6-二氯-N-(4-三氟甲基苄基)苯酰胺,2-氨基丁烷,2-苯基苯酚(OPP),硫酸8-羟基喹啉,顺式-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇,(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇,α-(1,1-二甲乙基)-β-(2-苯氧乙基)-1H-1,2,4-三唑-1-乙醇,1-[1-[2-[(2,4-二氯苯基)-甲氧基]苯基]乙烯基]-1H-咪唑,双(1-甲乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧]-2,5-硫代苯二羧酸酯,2,6-二氯-N-[[4-(三氟甲基)-苯基]甲基]苯甲酰胺,(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,9H-占吨-2-[(苯氨基)-羰基]-9-羧基酰肼,O-甲基S-苯丙基磷酰氨硫代酸酯,N-(5-氯-2-甲苯基)-2-甲氧基-N-(2-氧-3-恶唑烷基)乙酰胺,1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙烯酮-O-(苯甲基)肟,N-(2,6-二甲苯基)-2-甲氧基-N-(四氢-2-氧-3-噻吩基)乙酰胺,顺式-4-[3-[4-(1,1-二甲苯基)-苯基-2-甲丙基]-2,6-二甲基]吗啉盐酸盐,1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯啉二酮,1-甲基-5-壬基-2-(苯甲基)-3-吡咯啉二酮,1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,甲烷四硫醇钠盐,2-(2,3,3-三碘-2-丙烯基)-2H-四唑,N-[3-氯-4,5-双(2-丙炔基氧)-苯基]-N’-甲氧基甲咪唑酰胺,α-(5-甲基-1,3-二恶-5-基)-β-[[4-(三氟甲基)-苯基]亚甲基]-1H-1,2,4-三唑-1-乙醇,1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,N-(2,6-二甲苯基)-2-甲氧基-N-(四氢-2-氧-3-呋喃基)-乙酰胺,3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]乙基]-苯甲酰胺,N-甲酰基-N-羟基-DL-苯胺钠盐,N-(4-环己苯基)-1,4,5,6-四氢-2-嘧啶胺,4-甲基-四唑[1,5-a]喹唑啉-5(4H)-酮,2-氯-N-(2,6-二甲苯基)-N-(异硫代氰酰甲基)-乙酰胺,[(4-氯苯基)-偶氮]-氰乙酸乙酯,N-(4-己基苯基)-1,4,5,6-四氢嘧啶胺,N-(2-氯-4-硝基苯)-4-甲基-3-硝基苯磺酰胺,N-(氯乙酰基)-N-(2,6-二甲苯基)-DL-丙氨酸甲酯,3-[2-(4-氯苯基)-5-乙氧基-3-异恶唑啉基]-嘧啶,2-[(1-甲乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,螺旋[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮,N-(2,6-二甲苯基)-N-(5-异恶唑基羰基)-DL-丙氨酸甲酯,碳酸氢钾,1-[[2-(2,4-二氯苯基)-1,3-二氧-2-基]-甲基]-1H-咪唑,1-[(二碘甲基)磺酰基]-4-甲基苯,2-溴-2-(溴甲基)戊烷二腈,2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯[2,3-d]嘧啶-5-碳腈,1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-嘧啶羧酰胺,O,O-二乙基[2-(二丙氨基)-2-氧乙基]-乙基磷酰胺硫代酸酯,α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇,3-(1,1-二甲丙基-1-氧-1H-茚-2-碳腈,2,6-二氯-5-(甲基硫)4-嘧啶-硫代氰酸酯,1,2,3-苯并噻二唑-7-碳硫代酸S-甲酯,N-(6-甲氧基)-3-嘧啶基-环丙烷羧酰胺,3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧]-甲基]-苯甲酰胺,4-氯-2-氰-N,N-二甲基-5-(4-甲苯基)-1H咪唑基-1-磺酰胺,8-(1,1-二甲乙基)N-乙基-N-丙基-1,4-二氧螺旋(4,5)癸烷-2-甲胺,2,2-二氯-N-[1-(4-氯苯基)乙基]-1-乙基-3-甲基-环丙烷羧酰胺,N-(2,3-二氯-4-羟苯基)-1-甲基环已烷羧酰胺。杀菌剂:溴硝丙二醇,二氯芬,硝基吡,二甲基二硫氨基甲酸镍,春霉素,辛基异噻唑酮,呋喃羧酸,土霉素,噻菌灵,链霉素,烯丙异噻唑,硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:阿巴美丁,AC303630,高灭磷,acrinathrin,棉铃威,灭威,甲体氯氰菊酯,虫螨眯,阿凡曼菌素,AZ60541,印苦楝子素,谷赛昂A,谷赛昂M,唑环锡,thuringiensis杆菌,草虫威,丙硫克百威,地散磷,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷A,丁苯氨酯,噻嗪酮,布托萎锈灵,丁基哒螨酮,硫线磷,甲萘威,二硫磷,丁硫克百威,cartap,CGA157419,CGA184699 chloethocarb,chlorethoxyfos,毒虫畏,定虫隆,氯甲磷,毒死蜱,毒死蜱M,顺式-灭虫菊,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯,格林奈,三环锡,氯氰菊酯,环丙三氨三嗪,溴氰菊酯,内吸磷M,内吸磷S,内吸磷S-甲基,杀螨隆,二嗪磷,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,伏虫脲,乐果,dimethylvinphos,敌杀磷,乙拌磷,稻瘟光,emamectin,高氰戊菊酯,杀虫丹,乙赛昂,醚菊酯,灭克磷,etrimphos,克线磷,喹螨醚,杀螨锡,杀螟松,fenobucarb,苯硫威,双氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,杀灭菊酯,fipronil,氟啶胺,氟螨脲,氟氰戊菊酯,flufenprox,氯氟胺氰戊菊酯,地虫磷,安果,噻唑硫磷,fubfenprox,呋线威,HCH,蚜螨磷,氟铃脲,噻螨酮,咪蚜胺,iprobenfos,异唑磷,异丙胺磷,异丙威,异恶唑磷,伊维菌素,λ-格林奈,lufenuron,马拉硫磷,减蚜磷,mervinphos,甲硫芬,聚乙醛,methacrifos,甲胺磷,杀扑磷,灭虫威,灭多虫,metolcarb,milbemectin,久效磷,moxidectin,二溴磷,NC184,NI25,nitenpyram,氧乐果,草氨酰,砜吸磷,oxydeprofos,对硫磷A,对硫磷M,扑灭司林,稻丰散,甲拌磷,伏杀磷,亚胺硫磷,磷胺,肟硫磷,抗蚜威,虫螨磷M,溴丙磷,猛杀威,丙苯磷,残杀威,prothiofos,发果,pymetrozin,吡唑硫磷,边嗪硫磷,熏虫菊,除虫菊,哒螨酮,pyrimidifen,蚊蝇醚,喹硫磷,RH5992虫蔬果磷,sebufos,silafluofen,治螟磷,硫灭克磷,乙丙硫磷,tebufenozide,tebufenpyrad,tebupirimiphos,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫畏,thiafenox,硫双卡,thiofanox,甲基乙拌磷,硫磷嗪,thuringiensin,四溴菊酯,triarathen,三唑磷,triazuron,敌百虫,triflumuron,trimethacarb,蚜减多,XMC,xylylcarb,zetamethrin。
还可以混入其它与之的活性化合物,如杀草剂、肥料和生长调节剂。
这些活性化合物可以这样使用,也可以以其配方形式,或者以制得的使用形式,例如即用形溶液、悬浮液、可润湿的粉末、浆料、可溶的粉末、粉尘和颗粒。它们可以常规的方式使用,例如可以通过倾倒、喷雾、雾化、撒播、扬尘、发泡、刷涂等等,还可以通过超低溶剂法来使用这些活性化合物,或者注射活性化合物的制剂,或该化合物本身到土壤中。植物的种子也可以处理。
在植物部分的处理中,使用形式的活性化合物的浓度可以在基本范围内变化,通常它们为1-0.0001%重量,优选地为0.5-0.001%重量。
在处理种子时,通常每公斤种子需要0.001-50克,优选地为0.01-10克的活性化合物。
在处理土壤时,在作用位置需要0.00001-0.1%重量,优选地为0.0001-0.02%重量的活性化合物浓度。
用于保护工业材料的组合物通常由1-95,优选地10-75%重量活性化合物组成。
本发明的活性化合物的使用浓度取决于要控制的微生物的种类和发生情况以及取决于要保护的材料的组成。最佳使用速度可以通过实验来确定。通常使用浓度基于所保护的材料为0.001-5重量,优选地为0.05-1.0%重量。
如果需要,可以通过加入其它具有抗菌作用的化合物、杀真菌剂、杀菌剂、除草剂、杀虫剂或其它用于增加活性谱或获得特定的效果,如额外的防虫作用的化合物,由此增加根据本发明用于保护材料的活性化合物或由这些化合物制得的组合物、浓缩物或十分常见的配方的活性和活性谱。这此混合物可以比本发明的化合物具有更广谱的活性。
在室温下,一边搅拌一边滴加1.5克(0.01摩尔)2-甲基-4,5-二氢呋喃-3-碳酰氯在10毫升甲苯中的溶液到2.2克(0.01摩尔)4-氟-2-环辛基苯胺、1.0克三乙胺和40毫升甲苯的混合物中。在加料结束以后,将反应混合物在室温下再搅拌2小时。而后将反应混合物与水混合。分离开有机相,在硫酸钠上干燥并且减压浓缩。将余下的残留物与已烷一起搅拌。将所获得的结晶产物吸附过滤并在59℃下减压干燥。用这种方式可以获得2.2克(理论值的66.7%)N-(4-氟-2-环辛基)-2-甲基-4,5-二氢呋喃-3-羧酰胺,其形式为固体物质,熔点为91℃。
以相似的方式制备下表1中所列出的通式(Ⅰ)的二氢呋喃羧酰胺。
表1 表1-续表1-续表1-续表1-续表1-续表1-续表1-续表1-续表1-续表1-续*)1H-NMR谱,采用四甲基硅烷(TMS)作为内部标准记录在dentero氯仿(CDCl3)中。所说的化学位移以δ值(ppm)表示。用途实施例
在下列实施例中,采用下面列出的化合物作为对比物质:(A):2-甲基-4,5-二氢呋喃-3-羧酰苯胺(由DE-A-1914954获知)(B):2-甲基-4,5-二氢呋喃-3-N-(1,1,3-三甲基-二氢化茚-4-基)-羧酰胺(由J.Pesicide Sci.18(1993),245-251获知)实施例A灰霉病试验(豆)/保护溶剂 47份重量丙酮乳化剂: 3份重量烷芳基聚二醇醚
为了制得活性化合物的适当制剂,将1份重量的活性化合物与所说重量的溶剂和乳化剂混合并且用水将浓缩物稀释到所需的浓度。
为了试验保护活性,在幼年植物上喷涂活性化合物制剂,直到发霉。在喷雾涂层干燥后,将2小块琼脂(用灰霉病灰超时生长)放在每一片叶上。将培养后的植物放在20℃黑暗的潮湿环境下。
培养3天后,测定叶子上感染区域的尺寸并用%表示,0%表示对应于对照物的效率,而100%的效率表示没有看见感染。
为了制得活性化合物的适当制剂,将1份重量的活性化合物与所说重量的溶剂和乳化剂混合并且用水将浓缩物稀释到所需的浓度。
为了试验保护活性,在所说的涂覆位置在幼年植物上喷涂活性化合物制剂。
在喷雾涂层干燥后,将裸麦果糖丹毒丝菌-小麦的孢子撒在植物上。
将植物放在温室中,温度为20℃、相对湿度约为80%,以促进霉脓胞的生长。
培养7天后,进行评价,0%表示对应于对照物的效率,而100%的效率表示没有看见感染。
为了制得活性化合物的适当制剂,将1份重量的活性化合物与所说重量的溶剂和乳化剂混合并且用水将浓缩物稀释到所需的浓度。
为了试验保护活性,在幼年植物上喷涂活性化合物制剂,直到发霉。在喷雾涂层干燥后,将煤烟状单丝壳菌灰撒在植物上。将培养后的植物放在温室中,温度为23-24℃、相对湿度为约75%。
培养10天后进行评价,0%表示对应于对照物的效率,而100%的效率表示没有看见感染。
为了制得活性化合物的适当制剂,将1份重量的活性化合物与所说重量的溶剂和乳化剂混合并且用水将浓缩物稀释到所需的浓度。
为了试验保护活性,在幼年植物上喷涂活性化合物制剂,直到发霉。在喷雾涂层干燥后,用萍果痂萍果球腔菌锈发器官的水灰悬浮液培养植物。将培养后的植物放在温室中达一天,温度为20℃、相对湿度为约100%。
培养12天后进行评价,0%表示对应于对照物的效率,而100%的效率表示没有看见感染。
为了制备活性化合物的适当制剂,将0.2份重量活性化合物与99.8份重量上述溶剂混合。
在每一种情况下,将用麦芽汁氯化聚醚制得的琼脂在液相中与活性化合物制剂在涂覆位置混合。固化后,将所获得的营养介质用菌丝体片在27℃下保温培养,该菌丝片已经挖出了担子菌克隆体。
在贮存在27℃下3天或7天后通过温室菌丝体的生长以及以所获得的抑制百分比(与未处理的对照物相比)来进行评价。0%表示对应于对照物的生长抑制,而100%的效率表示没有看见生长出丝菌体。
在下表中列出了活性化合物、活性化合物浓度和试验结果。表E破坏木材的担子菌生长的抑制
真菌种类 | 在6ppm本发明的活性化合物下径向生长巨型克隆体的抑制百分比 | |
(28) | (42) | |
小梁粘褶菌地窖粉孢革菌胎盘孔菌虎纹褶孔层菌杂色革盖菌血色韧革菌 | 505030707070 | 6060508010080 |
Claims (7)
R1代表任意取代的环烷基、任意取代的双环烷基、任意取代的环链烯基、任意取代的环烷基烷基、任意取代的芳基、任意取代的芳氧基、任意取代的芳烷基或代表烷基,
X代表具有1-6个碳原子的烷基、卤素、具有3-8个碳原子的环烷基、具有1-6个碳原子的烷氧基、具有1-4个碳原子和1-5个卤素原子的卤代烷基或具有1-4个碳原子和1-5个卤素原子的卤代烷氧基,
m表示0-3的整数,
R2代表烷基、环烷基、任意取代的芳基或任意取代的芳烷基,
n表示0-3的整数,
R3表示烷基、环烷基,任意取代的芳基或任意取代的芳烷基以及
p表示0-3的整数。
R1代表具有3-8个碳原子的环烷基,该基团任选地被相同的或不同的具有1-4个碳原子的烷基基团单取代或三取代,代表具有7-12个碳原子的双环烷基,该基团任选地被相同的和不同的具有1-4个碳原子的烷基基团单取代或三取代,代表5-8个碳原子的环链烯基,该基团任选地被相同的或不同的具有1-4个碳原子的烷基基团单取代或三取代,或者代表在环烷基部分具有3-8个碳原子和在烷基部分具有1-4个碳原子的环烷基烷基,该基团任选地被相同的或不同的具有1-4个碳原子的烷基基团单取代或三取代,或者
代表苯基,该苯基可以被相同的或不同的取代基单或三取代,所说的取代基选自卤素和具有1-4个碳原子的烷基,或者
代表苯氧基,该苯氧基可以被相同的或不同的取代基单或三取代,所说的取代基选自卤素和具有1-4个碳原子的烷基,或者
代表在烷基部分具有1-4个碳原子的苯烷基,该苯烷基在苯基部分可以被相同的或不同的取代基单或三取代,所说的取代基选自卤素和具有1-4个碳原子的烷基,
或者代表具有1-12个碳原子的直链或支链烷基,
X代表具有1-4个碳原子的直链或支链烷基、氟、氯、溴、具有3-8个碳原子的环烷基、具有1-4个碳原子的直链或支链烷氧基、具有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷基或代表具有1或2个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基,
m表示0、1或2,
R2代表具有1-12个碳原子的直链或支链烷基、具有3-8个碳原子的环烷基,任选地被相同的或不同的选自卤素和具有1-4个碳原子的取代基单取代或三取代的苯基,或者代表在烷基部分具有1-4个碳原子的苯烷基,该苯烷基任选地被相同的或不同的选自卤素和具有1-4个碳原子的烷基的取代基单或三取代,
n表示0、1、2或3,
R3代表具有1-12个碳原子的直链或支链烷基,具有3-8个碳原子的环烷基,任选地被相同的或不同的选自卤素和具有1-4个碳原子的取代基单取代或三取代的苯基,或者代表在烷基部分具有1-4个碳原子的苯烷基,该苯烷基任选地被相同的或不同的选自卤素和具有1-4个碳原子的烷基的取代基单或三取代以及
p表示0、1、2或3。
3.制备根据权利要求1的具有通式(Ⅰ)的二氢呋喃-羧酰胺的方法,其特征在于在一种酸粘合剂的适当存在下以及在一种稀释剂的适当存在下将具有下列通式(Ⅱ)的2-甲基-4,5-二氢呋喃-3-碳酰卤与具有通式(Ⅲ)的胺起反应式中Hal表示氯或溴,
H2N-R (Ⅲ)式中R如上所定义。
4.杀菌制剂,其特征在于它们至少含有一种根据权利要求1的具有通式(Ⅰ)的二氢呋喃-羧酰胺。
5.根据权利要求1的具有通式(Ⅰ)的二氢呋喃-羧酰胺的用途,作为在农作物保护和材料保护中的杀菌剂。
6.用于在在农作物保护和材料保护中控制不需要的细菌的方法,其特征在于将根据权利要求1的具有通式(Ⅰ)的二氢呋喃-羧酰胺施加到细菌和/或它们的栖息地上。
7.制备杀菌制剂的方法,其特征在于将根据权利要求1的具有通式(Ⅰ)的二氢呋喃-羧酰胺与补充剂(Streckmitteln)和/表面活性剂混合。
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DE19629825A DE19629825A1 (de) | 1996-07-24 | 1996-07-24 | Dihydrofuran-carboxamide |
DE19629825.3 | 1996-07-24 |
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CN1113062C CN1113062C (zh) | 2003-07-02 |
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US (1) | US6107336A (zh) |
EP (1) | EP0915863B1 (zh) |
JP (1) | JP2000515146A (zh) |
KR (1) | KR100473829B1 (zh) |
CN (1) | CN1113062C (zh) |
AU (1) | AU3444097A (zh) |
DE (2) | DE19629825A1 (zh) |
ES (1) | ES2190538T3 (zh) |
WO (1) | WO1998003495A1 (zh) |
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PT1341757E (pt) | 2000-11-08 | 2006-12-29 | Syngenta Participations Ag | Pirrolecarboxamidas e pirrolecarbotiamidas e suas utilizações agroquímicas |
DE10222884A1 (de) * | 2002-05-23 | 2003-12-04 | Bayer Cropscience Ag | Furancarboxamide |
EP1548007A1 (en) | 2003-12-19 | 2005-06-29 | Bayer CropScience S.A. | 2-Pyridinylethylcarboxamide derivatives and their use as fungicides |
WO2005103006A1 (en) * | 2004-04-26 | 2005-11-03 | Bayer Cropscience Sa | 2-pyridinylcycloalkylcarboxamide derivatives useful as fungicides |
DE102004059725A1 (de) | 2004-12-11 | 2006-06-22 | Bayer Cropscience Ag | 2-Alkyl-cycloalk(en)yl-carboxamide |
EP2079739A2 (en) | 2006-10-04 | 2009-07-22 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
WO2009036494A1 (en) * | 2007-09-18 | 2009-03-26 | Jomune Pty Limited | Man-over-board rescue device |
KR101303786B1 (ko) * | 2009-01-06 | 2013-09-04 | 쇼와 덴코 가부시키가이샤 | N-(1-히드록시에틸)카르복실산 아미드 화합물 및 그 제조방법 |
CN102317259B (zh) | 2009-02-17 | 2015-12-02 | 拜尔农科股份公司 | 杀真菌n-(苯基环烷基)羧酰胺,n-(苄基环烷基)羧酰胺和硫代羧酰胺衍生物 |
US8653114B2 (en) * | 2010-06-03 | 2014-02-18 | Bayer Intellectual Property Gmbh | O-cyclopropylcyclohexyl-carboxanilides and their use as fungicides |
MX2013005407A (es) | 2010-11-15 | 2013-07-03 | Bayer Ip Gmbh | 5-halopirazolcarboxamidas. |
JP2013543858A (ja) | 2010-11-15 | 2013-12-09 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 5−ハロゲノピラゾール(チオ)カルボキサミド類 |
EP2662363A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole biphenylcarboxamides |
WO2016066644A1 (en) * | 2014-10-29 | 2016-05-06 | Bayer Cropscience Aktiengesellschaft | N-(phenylcycloalkyl)carboxamides and n-(phenylcycloalkyl)thiocarboxamides as fungicides |
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JPH02157266A (ja) * | 1988-12-12 | 1990-06-18 | Mitsubishi Kasei Corp | N−インダニルカルボン酸アミド誘導体およびこれを有効成分とする農園芸用殺菌剤 |
CA2081935C (en) * | 1991-11-22 | 2004-05-25 | Karl Eicken | Anilide derivatives and their use for combating botrytis |
US5223526A (en) * | 1991-12-06 | 1993-06-29 | Monsanto Company | Pyrazole carboxanilide fungicides and use |
DE4231517A1 (de) * | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
DE4445545A1 (de) * | 1994-12-20 | 1996-06-27 | Bayer Ag | Verwendung von Laurinsäureestern zum Steigern der Wirkung von Pyrazolcarboxamiden |
-
1996
- 1996-07-24 DE DE19629825A patent/DE19629825A1/de not_active Withdrawn
-
1997
- 1997-07-11 DE DE59709159T patent/DE59709159D1/de not_active Expired - Fee Related
- 1997-07-11 KR KR10-1999-7000426A patent/KR100473829B1/ko not_active IP Right Cessation
- 1997-07-11 CN CN97196706A patent/CN1113062C/zh not_active Expired - Fee Related
- 1997-07-11 WO PCT/EP1997/003693 patent/WO1998003495A1/de active IP Right Grant
- 1997-07-11 US US09/230,198 patent/US6107336A/en not_active Expired - Fee Related
- 1997-07-11 EP EP97930521A patent/EP0915863B1/de not_active Expired - Lifetime
- 1997-07-11 ES ES97930521T patent/ES2190538T3/es not_active Expired - Lifetime
- 1997-07-11 AU AU34440/97A patent/AU3444097A/en not_active Abandoned
- 1997-07-11 JP JP10506505A patent/JP2000515146A/ja not_active Ceased
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KR100473829B1 (ko) | 2005-03-07 |
EP0915863A1 (de) | 1999-05-19 |
DE19629825A1 (de) | 1998-01-29 |
DE59709159D1 (de) | 2003-02-20 |
CN1113062C (zh) | 2003-07-02 |
JP2000515146A (ja) | 2000-11-14 |
AU3444097A (en) | 1998-02-10 |
EP0915863B1 (de) | 2003-01-15 |
US6107336A (en) | 2000-08-22 |
KR20000067942A (ko) | 2000-11-25 |
ES2190538T3 (es) | 2003-08-01 |
WO1998003495A1 (de) | 1998-01-29 |
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