CN1300084C - 2-甲氧基二苯甲酮类化合物中间体及其制备方法 - Google Patents
2-甲氧基二苯甲酮类化合物中间体及其制备方法 Download PDFInfo
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- CN1300084C CN1300084C CNB021473153A CN02147315A CN1300084C CN 1300084 C CN1300084 C CN 1300084C CN B021473153 A CNB021473153 A CN B021473153A CN 02147315 A CN02147315 A CN 02147315A CN 1300084 C CN1300084 C CN 1300084C
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- Prior art keywords
- methyl
- compound
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- bromine
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- 238000002360 preparation method Methods 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
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- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 238000005893 bromination reaction Methods 0.000 claims description 5
- 150000002191 fatty alcohols Chemical class 0.000 claims description 5
- 230000031709 bromination Effects 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
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- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
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- 229910052625 palygorskite Inorganic materials 0.000 description 1
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- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
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- 238000005245 sintering Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
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- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 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
- 239000013008 thixotropic agent Substances 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 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
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 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
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本发明公开了有下式(I)的取代的二苯甲酮类化合物。化合物可用作高内吸性的杀真菌剂。
Description
本申请是申请日为1998年8月20日、申请号为CN98118632.7、发明名称为“杀真菌的2-甲氧基二苯甲酮类化合物”的中国专利申请的分案申请。
技术领域
本发明涉及某些二苯甲酮类化合物、它们的制备方法、含有这些化合物的组合物、用这些化合物来处理某地方以杀死该地方真菌的方法以及它们作为杀真菌剂的应用。
背景技术
食物生产要靠各种农业技术以保证满足人口增长的饮食需求能够得到满足、有营养并且很容易从食品储架上获得。杀真菌剂是这些世界各地均采用的农业技术中的一种。杀真菌剂是保护作物和食物以防真菌和真菌病害的农业化学化合物。作物和食物时常受到各种真菌生物的危害,如果不加防治,它们将毁坏作物,破坏收获。
特别是子囊菌,它是引起至今仍有危害(尤其对于谷物和果类作物)的白粉病的病因。然而,施加防治疾病量的杀真菌剂却会使目标植物发生药害损失。
本发明的化合物公开在欧洲专利申请EP 0 727 141(1996年8月21日公布)的通式中。EP申请公开了有抗致植物病真菌活性、但内吸性相当低的化合物。
EP申请中没有公开有取代的二苯甲酮,其中第一个苯基基团在2位被一个甲氧基基团取代,在6位被一个卤原子或一个烷基基团取代,第二个苯基基团被三个烷氧基和一个甲基基团取代。
发明内容
本发明提供了式I结构的化合物,
其中
R1是卤原子或烷基;
R2是氢、卤原子、或烷基、烷氧基或硝基;或R1和R2同时为-CH=CH-CH=CH-基团;
R3和R4分别是任意取代的烷基;
而n是0至3的整数。
化合物对各种作物有相当好的选择杀真菌活性以及较高的内吸性。
本发明的一个目的是提供内吸性高的杀真菌化合物。
本发明的另一个目的是提供通过用杀真菌有效量的化合物接触所述植物来防治不希望的真菌的方法。
本发明的另一个目的是提供含有化合物作为活性组分的选择性杀真菌组合物。
从下面的详细描述以及所附的权利要求,本发明的这些及其它目的和特征是显而易见的。
具体实施方式
惊奇地发现,式I化合物,
其中R1至R4以及n如上所述,它有相当好的抗致植物病真菌(尤其是那些引起白粉病的真菌)的杀真菌活性,而且有较高的内吸性。
一般地说,除非另有特指,本文所用的术语卤原子是指溴、碘、氯或氟原子,特别是溴、氯或氟原子,尤其是溴或氯原子。
任意取代的部分可以不取代,或有1个至尽可能多的取代基。典型的,有0至2个取代基。每个任意取代的基团分别被一个或多个卤原子、硝基、氰基、环烷基(最好是C3-6环烷基)、环烯基(最好是C3-6环烯基)、卤代烷基(最好是C1-6卤代烷基)、卤代环烷基(最好是C3-6卤代环烷基)、烷氧基(最好是C1-6烷氧基)、卤代烷氧基(最好是C1-6卤代烷氧基)、苯基、卤代或二卤代苯基或吡啶基基团取代。
一般地说,除非另有特指,本文所用的术语烷基和烷氧基基团或部分是指一个直链或支链的基团或部分。通常,这种基团最多有10个碳原子,特别是最多有6个碳原子。合适地,烷基或烷氧基部分有1至6个碳原子,较佳地有1至5个碳原子。较佳的烷基是甲基、乙基、正丙基、异丙基或正丁基。
本发明特别涉及一种有通式I的化合物,其中基团R1至R4的任何烷基部分可以是直链或支链的烷基,烷基最多含有10个碳原子,较佳的最多有9个碳原子,更佳的最多有6个碳原子,其中每一个任意取代的基团分别被一个或多个卤原子、硝基、氰基、环烷基(最好是C3-6环烷基)、环烯基(最好是C3-6环烯基)、卤代烷基(最好是C1-6卤代烷基)、卤代环烷基(最好是C3-6卤代环烷基)、烷氧基(最好是C1-6烷氧基)、卤代烷氧基(最好是C1-6卤代烷氧基)、苯基或吡啶基取代,其中苯基部分可任意被一个或两个选自卤原子、氰基、C1-6烷基和C1-6烷氧基的基团取代。
本发明特别涉及的通式I化合物中,R1是卤原子(特别是氯)、直链或支链的C1-10烷基(特别是直链的C1-3烷基基团),最佳的是没有取代或被至少一个任意取代的苯基取代的甲基。
本发明特别涉及的通式I化合物中,R2是氢原子或卤原子(特别是氯、溴或碘原子)、硝基、C1-10烷基或C1-10卤代烷基基团,最佳的是氢、氯或溴原子。如果R2不是氢,则它最好与基团R1的邻位连接。
本发明特别涉及的通式I化合物中,R3和R4分别是一个任选取代的直链或支链C1-5烷基,特别是直链C1-3烷基,最佳的是没有取代或有取代的甲基基团。这个甲基基团最好没有取代,或是被一个苯基基团取代,苯基基团没有取代或被1至5个,最好是1至2个卤原子、C1-4烷基或C1-4烷氧基取代。
根据式I的二苯甲酮化合物是油状、胶状、或主要是结晶固体物质,它具有有用的杀真菌性能。例如,它们可以用于农业或相关领域如园艺和葡萄栽培中,以防治致植物病真菌尤其是子囊菌,特别可用于防治那些例如由禾白粉菌(Erysiphe graminis)、苹果白粉病菌(Podosphaera leucotricha)和葡萄钩似壳(Uncinula necator)等所引起的白粉病。所述二苯甲酮类化合物在很大浓度范围内均有很高的杀真菌活性,它可用于农业而不会产生有害的植物药害作用。
而且,本发明的化合物表现出对真菌和真菌病如谷物、黄瓜和葡萄白粉病的治愈和残余防治效果增强,而且与传统的杀真菌剂相比,叶片内吸性有所改善。
通过使用由式I确定的化合物可获得防治致植物病真菌的有用结果,式I中:
R1是氯原子或甲基;
R2是氢、氯或溴原子;
R3是C1-5烷基基团;
R4是C1-5烷基基团或被一个或多个氯原子或一个或多个C1-4烷基或烷氧基基团取代的苄基;
且n是0或2,特别是0。
如果R2是Cl或Br,它最好与基团R1在苯环邻位相接。
式IA的化合物是特别佳的:
其中
R1是氯原子或甲基,
R2是氢、氯或溴原子或甲基,
而R′是氢原子或C1-4烷基或是被一个或多个氟原子或一个或多个C1-4烷基基团任选取代的苯基基团。
式IB的化合物是特别佳的:
其中
R′是氢原子或C1-4烷基或是被一个或多个氟原子或一个或多个C1-4烷基基团任选取代的苯基基团。
通过采用例如式I的下列化合物可获得非常好的防治植物真菌病害效果:
6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮,
6,6′-二甲基-3′-戊氧基-2,2′,4′-三甲氧基-二苯甲酮,
5-溴-6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮,
5-氯-6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮,
5-碘-6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮,
6-氯-6′-甲基-2,2′,3′,4′-四甲氧基-二苯甲酮,
5-溴-6-氯-6′-甲基-2,2′,3′,4′-四甲氧基-二苯甲酮,
6-氯-5,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮,
2′-正丁氧基-6-氯-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮,
2′-正丁氧基-6-氯-5,6′-二甲基-2,2′,3′-三甲氧基-二苯甲酮,
6-氯-2′-(2-氟代苄氧基)-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮,
6-氯-2′-(4-氟代苄氧基)-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮,
5-溴-6,6′-二甲基-3′-正戊氧基-2,2′,4′-三甲氧基-二苯甲酮,
6-氯-6′-甲基-2′-正戊氧基-2,3′,4′-三甲氧基-二苯甲酮,
6-氯-2′-(3-甲基丁氧基)-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮,
2′-苄氧基-6-氯-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮,
6-氯-2′-(3-甲基苄氧基)-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮,
6-氯-2′-(4-甲基苄氧基)-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮,
6-氯-2-二氟代甲氧基-6′-甲基-2′,3′,4′-三甲氧基-二苯甲酮,
1-(6-甲基-2,3,4-三甲氧基苯甲酰基)-2-甲氧基萘,
1-(6-甲基-2,3,4-三甲氧基苯甲酰基)-2-二氟代甲氧基萘。
本发明还提供了制备式I化合物的方法(A),其中n是0,方法包括用甲醇碱金属盐最好是甲醇钠来处理通式II化合物,
其中R1、R2、R3、R4如前所述,X表示氟或氯原子。
另一种可行的制备式I化合物的方法是方法(B),方法包括步骤
(a)在路易斯酸(Y=离去基团)或脱水剂(Y=OH),最好是五氧化二磷或POCl3存在下,使式III化合物
其中R1、R2和n如前所述,Y是一个离去基团,特别是一个氯原子或羟基基团,与式IV化合物反应,
其中R3如权利要求1所定义;和
(b)用式V化合物来任选处理得到的式I所示的二苯甲酮(其中R4是甲基),
R4-O-Met (V)
其中R4是任选取代的非甲基烷基基团,Met表示一个碱金属原子,最好是钠。
式III化合物(其中R2是卤原子)最好通过方法(C)获得,方法包括
(a)使式VI的化合物与卤化剂反应,
其中R1和n如权利要求1所定义,R″是氢原子或烷基,
(b)任选水解得到的卤化的苯甲酸烷酯(R″=烷基),和
(c)用亚硫酰氯任选处理获得的卤化的苯甲酸。
式II、IV、V和VI的起始物是已知产品,式III起始物是部分已知部分新的产品。
因此,本发明提供了式IIIA的新的中间产物,
其中R1是烷基,尤其是甲基。
式II、IV、V和VI的起始物可根据已知的方法或其常规改良法制备。与所选反应条件不相容的取代基可以在形成二苯甲酮后引入。它们可用已知的方法,例如随后的衍生、合适基团的取代或通过消除合适的保护基团来生成。
式II的2-卤代二苯甲酮和碱金属甲醇盐之间的反应最好在溶剂如醚(例如四氢呋喃、***、叔丁基-甲醚)或二甲氧基乙烷、甲醇及这些溶剂的混合物中进行。在25至120℃内,式II化合物和碱金属甲醇盐间的摩尔比最好在0.3至1.9间。
根据已知方法(Y=Cl),式III和IV化合物间的弗瑞德-克来福特反应在路易斯酸催化剂存在下才有效。合适的催化剂包括FeCl3,AlCl3,SnCl4,ZnCl2,TiCl4,SbCl5和BF3,它们可以用等摩尔当量(以式III苯甲酰氯计)。然而,也可在升高的温度下(较佳的是在回流温度下)采用较少量的催化剂,在这些条件下较佳的催化剂是FeCl3、I2、ZnCl2、铁、铜、强的磺酸如F3CSO3H和酸性离子交换树脂如AMberlyst15和Nafion。在约50至180℃下,较佳的催化剂是0.001至0.2摩尔比的FeCl3。反应可在反应条件下在惰性溶剂例如氯化乙烯、二氯甲烷、苯、辛烷、癸烷或混合溶剂中进行,或是在没有溶剂下而是方便地用一种反应物过量(如在1∶5至5∶1范围内)来进行。如果用AlCl3,在通常为-10至70℃的温度下,摩尔比最好在0.5至2之间,合适的溶剂例如是二氯甲烷或氯化乙烯。
在本发明的另一个较佳的方法中,式III的苯甲酸(Y=OH)在五氧化二磷存在下,在大约0至50℃下(最好在室温下),或是在POCl3存在下,在约50至150℃下(最好在回流温度下)与式IV化合物反应。
式VI苯甲酸酯的卤化最好在惰性溶剂存在下进行。较佳的卤化剂例如是磺酰氯、磺酰溴和N-碘代-琥珀酰亚胺。如果R1是卤原子,则高极性溶剂如醇或羧酸,特别以乙酸较佳。如果R1是烷基,特别是甲基,则非极性溶剂以四氯化碳较佳。如果反应在0至40℃下(最好在室温下)与溴进行,则卤化主要发生在R1基团的邻位。
R2为溴原子的式III化合物的较佳例子是将式VI的化合物与溴反应制得的,式VI中R1是烷基,n是0,R″是氢原子。这步溴化最好在极性质子溶剂,例如脂族醇或脂族羧酸,特别是在乙酸中进行。溴化反应以在弱碱或缓冲体系如乙酸钠或碳酸钠中进行为好。
本发明方法实例之一是,以式VI起始化合物计,方法中溴的用量为1.0至1.5摩尔当量,特别可选用1.05至1.2摩尔当量。
式VI的化合物与溴之间的反应通常在足以使式VI化合物转变成式III化合物的最佳温度下进行。这表示温度应足够高,以维持转变,但又要足够低,以避免起始物和产品的分解。反应最好在0至40℃的温度下,特别是在室温下进行。
式VI的化合物与溴之间的反应通常要进行足够长的时间,以使式VI化合物最适当地转变成式III化合物。这表示反应时间应足够长,以使最大量的起始物转变成式III化合物。反应最好能进行1至40小时,特别是5至24小时。
如果需要的话,下面描述的方法可类似地应用于其它起始化合物。
由于良好的植物耐受性,式I化合物可用于所有不希望被待防治真菌感染的的栽培植物,如谷物、蔬菜、豆类、苹果树、葡萄藤。在防治真菌用量下,目标作物没有植物毒性是本发明的一个特点。
因此,本发明还提供了一种杀真菌组合物,它包含一种载体和至少一种前述式I的化合物作为活性组分。本发明也提供了制备这种组合物的方法,方法包括将上述定义的式I化合物与至少一种载体结合。这种组合物可含有本发明的一种化合物或几种化合物的混合物。预计不同的异构体或异构体的混合物可以有不同的活性水平或活性谱,因此组合物可以包括单个异构体或异构体的混合物。
本发明的组合物最好含有0.5%至95%重量的活性组分。
本发明组合物中的载体是任何配制入活性组分,以便于施加到待处理地方(例如可以是植物、种子或土壤),或便于储藏、运输或操作的材料。载体可以是固体或液体,包括通常为气态但被压缩成液体的材料,任何通常用于配制杀真菌组合物的载体均可采用。
组合物可以根据已有技术生产成例如浓缩乳剂、可直接喷洒或稀释的溶液、稀乳剂、可湿性粉剂、可溶性粉剂、粉剂、颗粒剂、水可分散性粒剂、微胶囊剂。施加的形式例如是喷洒、雾化、分散、倾倒,和组合物一样,这可根据希望的目标及给定的环境来选择。
制剂,即包含至少一种通式I化合物和任选的固体和/或液体助剂和佐剂的组合物,可根据已有技术来制备,例如使活性组分与其它物质,例如填充剂、溶剂、固体载体和任选的表面活性化合物或佐剂一起充分混合和/或研磨。
溶剂可以是芳烃,最好是C8至C12组分,如二甲苯类或二甲苯类混合物,有取代的萘、苯二甲酸酯(如苯二甲酸二丁酯或苯二甲酸二辛酯);或是脂族烃如环己烷或石蜡,醇和二醇及其它们的醚和酯,如乙醇、乙二醇单甲醚和乙二醇二甲醚,酮如环己酮,强极性溶剂如N-甲基-2-吡咯烷酮、二甲基亚砜、烷基甲酰胺,环氧化植物油如环氧化椰子油或环氧化豆油,水。通常,以不同液体的混合物为宜。
可用作粉剂或可分散性粉剂的固体载体可以是矿物填充剂,如方解石、滑石、高岭土、蒙脱石、绿坡缕石。通过加入高分散性硅胶或高分散性聚合物可改善物理性质。颗粒载体可以是多孔材料,如浮石、碎砖、海泡石、膨润土,非吸着性载体可以是方解石或砂。因此,可采用多种预先粒化的无机或有机材料,如白云石或压碎的植物残渣。
杀真菌组合物通常以浓缩形式配制和运输,然后由使用者在施加前稀释。少量载体表面活性剂的存在可使这种稀释能够进行。因此,本发明组合物中的一种载体最好是一种表面活性剂。例如组合物可含有至少两者载体,其中至少一种是表面活性剂。
根据待配制的通式I化合物的特点,合适的表面活性物质可以是有良好的分散性、乳化性和润湿性的非离子型、阴离子或阳离子型表面活性剂。表面活性剂也可以指表面活性剂的混合物。
合适的表面活性剂可以是所谓的水溶性肥皂和水溶性合成的表面活性化合物。
肥皂通常是高级脂肪酸(C10-C20)的碱金属、碱土金属或任选取代的铵盐,例如油酸、硬脂酸或天然脂肪酸的混合物(可从例如椰子油或动物脂制得)的钠盐或钾盐。另外,可用脂肪酸的甲基-牛磺酸盐。
然而,最好采用所谓的合成的表面活性剂,特别是脂族磺酸盐、脂族硫酸盐、磺化的苯并咪唑衍生物或烷基芳基磺酸盐。
脂族硫酸盐或脂族磺酸盐通常采用碱金属盐、碱土金属盐或任选取代的铵盐,烷基部分有8至22个碳原子,其中烷基也指酰基基团的烷基部分,如木素磺酸、十二烷基硫酸或脂族醇的混合物(从天然脂肪酸制得)的钠盐和钙盐。这也包括硫酸酯、磺酸及脂族醇和环氧乙烷的加合物的盐。磺化的苯并咪唑衍生物最好含有2个磺酸基团和一个有8至22个碳原子的脂肪酸基团。烷基芳基磺酸盐例如是十二烷基苯磺酸、二丁基萘磺酸或萘磺酸和甲醛的缩合物的钠盐、钙盐或三乙基铵盐。
而且,可以采用磷酸盐,如磷酸酯的对-壬基酚-(4-14)-环氧乙烷加合物或磷脂的盐。
非离子表面活性剂最好是脂族或环脂族醇、饱和或不饱和脂肪酸和烷基酚的聚乙二醇醚的衍生物,它有3至10个乙二醇醚基团,(脂族)烃基团中有8至20个碳原子,烷基酚的烷基基团中有6至18个碳原子。
其它合适的非离子型表面活性剂是水溶性的20至250乙二醇醚基团,它含有环氧乙烷和聚丙二醇的加聚物,乙二氨基聚丙二醇和烷基聚丙二醇(烷基部分有1至10个碳原子),该产物通常每个丙二醇单元中含有1至5个乙二醇。
非离子型表面活性剂的例子包括壬基酚聚乙氧基乙醇,蓖麻油聚乙二醇醚、环氧乙烷和聚丙烯的加成聚合物、三丁基苯氧基聚乙氧基乙醇、聚乙二醇、辛基苯氧聚乙氧基乙醇。
另外,可用聚氧乙烯山梨糖醇的脂肪酸酯,如三油酸聚氧乙烯山梨糖酯。
阳离子表面活性剂最好至少有一个8至22个碳原子的烷基基团,且有低碳的、任选卤化的烷基、苄基或羟烷基的季铵盐。而盐最好是卤化物、甲基硫酸盐或烷基硫酸盐,如硬脂酰三甲基氯化铵或苄基二(2-氯乙基)乙基溴化铵。
本发明的组合物例如可以制成可湿性粉剂、粉剂、颗粒剂、溶液、可乳化的浓缩乳剂,悬浮浓缩剂和气溶胶。可湿性粉剂通常含有25%、50%或75%w/w活性组分,而且除固体惰性载体外,它通常还含有3%-10%w/w分散剂,需要的时候,还可含有0%-10%w/w的稳定剂和/或其它添加剂如渗透剂或粘着剂。粉剂通常是制成与可湿性粉剂组成相同只是不含分散剂的粉剂浓缩物,浓缩物可在田间进一步用固体载体稀释,以形成通常含0.5%-10%w/w活性组分的组合物。颗粒剂通常制成大小为10至100目ASTM(约2.00mm-0.15mm),它可用烧结或浸渍技术来生产。通常,颗粒剂含有0.5%-75%活性组分和0-10%w/w添加剂如稳定剂、表面活性剂、缓释改性剂(slow felease modifier)和粘合剂。所谓的“可流动干粉(dryflowable powders)”由相当小的活性组分浓度相当高的颗粒组成。可乳化的浓缩物除了溶剂或溶剂混合物外,通常还含有1%-50%w/v活性组分,2%-20%w/v乳化剂和0%-20%w/v其它添加剂如稳定剂、渗透剂和缓蚀剂。悬浮浓缩剂通常经混配(compound)以获得稳定的、无沉积的可流动产品,它通常含有10%-75%w/w活性组分,0.5%-15%w/w分散剂,0.1%-10%w/w悬浮剂如保护性胶体和触变剂,0%-10%其它添加剂如消泡剂、缓蚀剂、稳定剂、渗透剂和粘着剂,以及水或一种基本上不溶解活性组分的有机液体;制剂中可溶解有某些有机固体或无机盐,以防止沉积或对水的防冻剂。
水性分散剂和乳剂,例如通过将本发明的可湿性粉剂或浓缩物稀释入水中以获得组合物,也在本发明范围内。所述的乳剂可以是油包水型或水包油型,并有类似蛋黄酱那样厚的稠度。
本发明的组合物也可含有其它组分,例如有除草、杀虫或杀真菌性能的其它化合物。
在提高本发明化合物持久保护活性方面,特别有意义的是采用可将杀真菌化合物缓慢释放入待保护植物环境中的载体。这种缓慢释放制剂可以例如施加到植物根部邻近的土壤中,或可以包含一种粘合性成分,使得它们可以直接施加于植物茎部。
作为商品,组合物最好是浓缩的形式,而最终使用者通常用的是稀释的组合物。组合物可以稀释成浓度为0.001%的活性组分(a.i.)。剂量通常在0.01至10公斤活性组分/公顷范围内。
本发明的组合物也可包含其它有生物活性的化合物,例如有类似或补充杀真菌活性的化合物或是调节植物生长、除草或杀虫活性的化合物。
其它杀真菌化合物可以是,例如,一种可以抗谷物(如小麦)疾病(例如那些由白粉病菌属(Erysipha)、柄锈病菌属(Puccinia),壳针孢菌(Septoria),赤霉病菌属(Gibberella)和长蠕孢属(Helminthosporium spp.)引起的疾病)、种子和土壤传病、和葡萄藤上的霜霉病和白粉病以及苹果树上的白粉病和疮痂病等的化合物。这些杀真菌剂的混合物比单用通式I的混合物有更广谱的活性。
其它化合物的例子是多通灵、苯菌灵、甲基托布津、涕必灵、麦穗宁、土菌灵、抑菌灵、霜脲氰、亚酰胺、甲呋酰胺、甲霜灵、福拉莱尔(furalaxyl)、苯霜灵、乙磷铝、氯苯嘧啶醇、异菌脲、普罗西密啶(procymidione)、乙烯菌核利、苯系纳唑(pencinazole)、腈菌唑、R0151297、S3308、吡嘧磷、乙菌定、迪塔里佛斯(ditalimfos)、十三吗啉、嗪氨灵、氟苯嘧啶醇、***丁基(triazbutyl)、双胍盐、丙环唑、普罗克络拉(prochloraz)、粉唑醇、己唑醇、氟硅唑、***酮、特莱叮诺(triadimenol)、苄氯***醇、丁苯吗啉、啶斑肟、环唑醇、戊唑醇、环氧康唑(epoxiconazole)、4-Cl-N-(氰基(乙氧基)甲基)苯甲酰胺、苯锈啶、乙菌利、烯唑醇、异麻杂利(imazalil)、甲呋酰苯胺、萎锈灵、氧化萎锈灵、呋菌胺、十二环吗啉、灭瘟素、春雷霉素、克瘟散、异稻瘟净、放线菌酮、四氯苯酞、噻菌灵、富士一号、三环唑、咯喹酮、灭瘟唑、甲胂铁铵、多氧霉素、有效霉素、灭锈胺、氟酰胺、戊菌隆、哒菌清、叶枯净、二甲基二硫代氨基甲酸镍、叶枯酞、双苯***醇、乙嘧酚磺酸酯、异康纳唑(etaconazole)、链霉素、酯菌胺(cypofuran)、双苯***醇、喹甲硫酯、甲菌定、1-(2-氰基-2-甲氧基亚氨基-乙酰基)-3-乙基脲、丁基苯基咪唑丙腈、托壳勒福斯甲基(toclofosmethyl)、吡络福(pyroxyfur)、代森联、代森锰、代森锌锰、敌菌丹、百菌清、敌菌灵、福美双、克菌丹、费而顿、代森锌、甲基代森锌、硫黄粉、敌螨普、乐杀螨、硝基铊异丙基(nitrothalisopropyl)、多果定、二噻农、毒菌锡、薯瘟锡、四氯硝基苯、五氯硝基苯、氯硝胺、含铜化合物如氯氧化铜、硫酸铜和波尔多液以及有机汞化合物、克莱新-甲基(kresoxim-methyl)、氧化偶氮基黑蚜虫红色素(azoxystrobin)、SSF-126、吡甲尼(pyrimethanil)、塞坡迪尼(cyprodinil)、斯吡洛克斯胺(spiroxamine)、氟二氧尼(fludioxonil)、喹啉酚(quinoxyfen)、卡丙酰胺(carpropamid)、甲新唑(metcinazole)、烯酰吗啉、法酮(famoxadone)、霜霉威(propanocarb)、氟甲奥福(flumetover)、拌种咯、氟偶氮安(fluazinam)、麦帕尼吡啉(mepanipyrim)、***氧(triazoxide)、百菌清。
此外,本发明的共同制剂(co-formulation)可含有至少一种式I的二苯甲酮和下列生物防治剂(如病毒、细菌、线虫、真菌)的任一种,以及其它适用于防治昆虫、杂草或植物疾病或用来诱导植物中的宿主抗性的微生物。这些生物防治剂的例子是:苏云金芽胞杆菌(Bacillus thuringiensis)、Verticillium lecanii,Autographicacalifornica NPV、Beauvaria bassiana、Ampelomyces quisqualis、Bacilis subtilis、Pseudomonas fluorescens、Strptomyces griseoviridis和Trichoderma harzianum。
另外,本发明的复配制剂可含有至少一种式I二苯甲酮和诱导植物内吸而获得抗性的化学试剂,例如烟酸或其衍生物或BION。
通式I的化合物可与土壤、泥煤或其它根部介质混合,来保护植物以防种子传病、土壤传病或叶真菌病。
本发明还提供了上述通式I的化合物或上述的组合物作为杀真菌剂的应用,以及一种抗某地方的真菌的方法,方法是用这种化合物或组合物来处理某地方,某地方可以是受真菌侵袭的植物、这种植物的种子或这种植物生长或将要在其中生长的基质。
本发明在保护作物和观赏性植物以防真菌侵袭方面有广泛的应用。典型的待保护作物包括葡萄藤、谷类作物如小麦和大麦、稻、甜菜、树顶水果(top fruit)、花生、马铃薯、蔬菜和西红柿。保护的耐用性通常由所选的单个化合物、以及各种外部因素(如气候,它的影响通常可通过使用合适的制剂来减小)来决定。
下列实施例进一步描述了本发明。然而,应当理解本发明不仅仅下面给出的
具体实施例。
实施例1
6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮的制备
1A 2-甲氧基-6-甲基苯甲酸
2-甲氧基-6-甲基苯甲酸乙酯(5.0g,25毫摩尔)、水(10ml)、甲醇(40ml)和氢氧化钠(2.1g,50毫摩尔)的混合物在搅拌下回流加热。反应混合物用水(150ml)稀释,并用浓盐酸酸化。过滤收集固体物,用水洗并干燥,得到暗黄色晶体2.1g(熔点136℃)。
1B 2-甲氧基-6-甲基苯甲酰氯
将1A(1.7g,10.2毫摩尔)和亚硫酰氯(2ml)的混合物回流加热1小时。浓缩混合,得到的苯甲酰氯即可使用而不需进一步纯化。
1C 6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮
将3,4,5-三甲氧基二甲苯(1.86g;10.2毫摩尔)、1B(10.2毫摩尔),氯化铝(1.33g,10毫摩尔)和二氯甲烷(20ml)的混合物在0℃下搅拌。反应设定在0℃,生成氯化氢。然后,反应混合物再在室温下搅拌4小时。然后,在0℃下缓缓加入稀盐酸和乙酸乙酯的混合物(1∶1v/v;100ml)。浓缩有机相,残余物自甲醇重结晶出。用真空吸滤收集固体物,用甲醇/水洗三次(3∶1v/v;每次100ml),干燥而获得白色晶体1.0g(30.3%,熔点84℃)。
实施例2
6,6′-二甲基-2′-正丁氧基-2,3′4′-三甲氧基-二苯甲酮的制备
搅拌正丁醇(5ml)和氢化钠(60%,在油中,l0毫摩尔)的混合物直至不再生成H2。将1C(0.7g,2.2毫摩尔)和二甲氧基乙烷(15ml)的混合物加入得到的反应混合物中。然后,反应混合物回流加热并搅拌24小时。然后在室温下缓缓加入水和乙酸乙酯的混合物(1∶1v/v;100ml)。分离浓缩有机相,残余物用柱层析(石油醚∶乙酸乙酯,95∶5v/v)来纯化,得到黄色油状的纯产物0.2g(24.4%)。
实施例3
6-氯-2′-戊氧基-6′-甲基-2,3′,4′-三甲氧基-二苯甲酮的制备
将甲醇中的甲醇钠(5.4摩尔/升,19.6毫摩尔)、2,6-二氯-3′,4′-二甲氧基-6′-甲基-2′-戊氧基-二苯甲酮(根据EP 0 727 141获得,2.69g,6.5毫摩尔)和二甲氧甲烷(20ml)的混合物在80℃下加热搅拌24小时。然后在室温下缓缓加入水和乙酸乙酯的混合物(1∶1v/v;100ml)。分离浓缩有机相,残余物用柱层析(二氯甲烷)提纯,得到黄色油状的纯净产物0.52g(19.7%)。
实施例4
5-溴-6-氯-6′-甲基-2,2′,3′4′-四甲氧基-二苯甲酮的制备
4A 5-溴-6-氯-2-甲氧基苯甲酸乙酯
将6-氯-2-甲氧基苯甲酸乙酯(1.8g,8.4毫摩尔)、溴(1.41g,8.8毫摩尔)和乙酸(5ml)的混合物在室温下搅拌24小时。将反应混合物倒入水中并用乙酸乙酯抽提。分离浓缩有机相,残余物用柱层析(石油醚∶乙酸乙酯,95∶5v/v)来纯化,得到黄色油状的纯净产物1.7g(69.%)。
4B 5-溴-6-氯-2-甲氧基苯甲酸
4A(1.7g,5.8毫摩尔)、水(10ml)、乙醇(20ml)和氢氧化钠(0.5g,12.5毫摩尔)的混合物回流加热并搅拌。反应混合物用水(80ml)稀释并用浓盐酸酸化。过滤收集固体物,用水洗并干燥获得白色晶体1.3g(85%),熔点为186-188℃。
4C 5-溴-6-氯-2-甲氧基苯甲酰氯
4B(1.2g,4.6毫摩尔)、二氯甲烷(15ml)和草酰氯(1ml)的混合物在室温下搅拌2小时。浓缩混合物,得到的苯甲酰氯即可使用而无需进一步纯化。
4D 5-溴-6-氯-6′-甲基-2,2′,3′,4′-四甲氧基-二苯甲酮
3,4,5-三甲氧基二甲苯(0.83g;4.6毫摩尔)、4C(4.6毫摩尔),氯化铝(0.62g,4.6毫摩尔)和二氯甲烷(20ml)的混合物室温下搅拌3小时。然后,加入水和乙酸乙酯的混合物(1∶1v/v;50ml)。浓缩有机相,残余物从二异丙醚中结晶出并自甲醇重结晶出。用真空吸滤收集固体物,用水洗并干燥获得黄色晶体0.7g(35.4%,熔点87-88℃)。
实施例5
1-(6′-甲基-2′,3′,4′-三甲氧基苯甲酰基)-2-甲氧基萘的制备
5A (2-甲氧基萘-1-基)羧酸甲酯
2-羟基萘-1-基羧酸(18.82g,100毫摩尔)、氢氧化钠(8.8g,220毫摩尔)、硫酸二甲酯(31.5,250毫摩尔)和水(200ml)的混合物在70℃下加热搅拌20小时。然后,反应混合物冷却至室温用乙酸乙酯抽提两次。浓缩合并的有机相,残余物即可使用而不需进一步纯化。
5B 甲基(2-甲氧基萘-1-基)羧酸
粗制的5A(10.5g,48毫摩尔)、水(100ml)、甲醇(150ml)和氢氧化钠(12g,300毫摩尔)的混合物在搅拌下回流加热。反应混合物用***抽提两次。过滤水性反应混合物并用浓盐酸酸化。过滤收集固体物,用水洗并干燥获得黄色晶体9.45g(97.4%,熔点175-176℃)。
5C 1-(6′-甲基-2′,3′,4′-三甲氧基苯甲酰基)-2-甲氧基萘
5B(2.02g,10毫摩尔)、3,4,5-三甲氧基二甲苯(1.82g;10毫摩尔)、P2O5(10.0)和二氯甲烷的混合物在室温下搅拌16小时。然后,蒸馏除去二氯甲烷,残余物用乙酸乙酯稀释。有机相用水洗并浓缩。残余物用柱层析(石油醚∶乙酸乙酯,8∶2v/v)纯化,并从石油醚∶二异丙醚(1∶1v/v)重结晶。真空吸滤收集固体物,固体物用冷的石油醚∶二异丙醚(1∶1v/v)洗并干燥,获得白色晶体0.9g(24.6%,熔点为72℃)。
实施例6
5-溴-6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮的制备
6A 5-溴-6-甲基-2-甲氧基苯甲酸乙酯
6-甲基-2-甲氧基苯甲酸乙酯(8.4g,43.2毫摩尔)、溴(6.9g,43.2毫摩尔)和四氯甲烷(170ml)的混合物在室温下搅拌60小时。将反应混合物倒入水中并用乙酸乙酯抽提。分离浓缩有机相。得到黄色油状的粗制产物10.3g(87.%)。
6B 5-溴-6-甲基-2-甲氧基苯甲酸
6A(9.8g,34.1毫摩尔)、水(40ml)、乙醇(80ml)和氢氧化钠(2.7g,68.3毫摩尔)的混合物回流加热并搅拌42小时。反应混合物用水(80ml)稀释,用浓盐酸酸化,并用二氯甲烷抽提。分离浓缩有机相。过滤收集固体物,用水洗并干燥获得灰白色晶体5.4g(61%),熔点为81-83℃。
6C 5-溴-6,6′-二甲基-2,2′,3′,4′-四甲氧基二苯甲酮
6B(24g,10毫摩尔)、3,4,5-三甲氧基二甲苯(1.82g;10毫摩尔)、P2O5(10.0g)和二氯甲烷(1500ml)的混合物室温下搅拌16小时。然后,蒸馏除去二氯甲烷,残余物用乙酸乙酯稀释。有机相用水洗并浓缩。残余物用柱层析(石油醚∶乙酸乙酯,8∶2v/v)纯化,并从二异丙醚中重结晶出。真空吸滤收集固体物,固体物用冷的石油醚∶二异丙醚(1∶1v/v)洗并干燥,获得白色晶体2.2g(54%,熔点为89-91℃)。
实施例7-49
用基本上与上述实施例1至6相同的步骤,并采用合适的标准衍生技术,制备表I和II中下列化合物:
表I
实施例 | R1 | R2 | R3 | 熔点(℃) |
7 | H | 甲基 | 甲基 | 95 |
8 | 正丙基 | 甲基 | 甲基 | 油 |
9 | 正丁基 | 甲基 | 甲基 | 油 |
10 | H | H | 甲基 | 51 |
11 | 正丙基 | H | 甲基 | 油 |
12 | 2-甲基丙基 | H | 甲基 | 55-56 |
13 | 苯基 | H | 甲基 | 120-122 |
14 | 4-氟代苯基 | H | 甲基 | 96-98 |
15 | 4-甲基苯基 | H | 甲基 | 80 |
16 | 3-甲基苯基 | H | 甲基 | 90-93 |
17 | 2-氟代苯基 | H | 甲基 | |
18 | 2-甲基丙基 | 甲基 | 甲基 | |
19 | 苯基 | 甲基 | 甲基 | |
20 | 4-氟代苯基 | 甲基 | 甲基 | |
21 | 4-甲基苯基 | 甲基 | 甲基 | |
22 | 3-甲基苯基 | 甲基 | 甲基 | |
23 | 2-氟代苯基 | 甲基 | 甲基 | |
24 | 正丙基 | Br | 甲基 | |
25 | 正丁基 | Br | 甲基 | |
26 | 2-甲基丙基 | Br | 甲基 | |
27 | 苯基 | Br | 甲基 | |
28 | 4-氟代苯基 | Br | 甲基 | |
29 | 4-甲基苯基 | Br | 甲基 | |
30 | 3-甲基苯基 | Br | 甲基 | |
31 | 2-氟代苯基 | Br | 甲基 | |
32 | 正丙基 | H | 正丁基 | 油 |
33 | H | 甲基 | 丙酰基 | |
34 | H | 甲基 | H | |
35 | H | 甲基 | 正丙基 | 油 |
36 | H | 甲基 | 正丁基 | 油 |
37 | H | 甲基 | 正戊基 | 油 |
38 | H | 甲基 | 3-甲基-丁基 | 油 |
39 | H | NO2 | 甲基 | 油 |
表II
实施例 | n | R1 | R2 | R′ | R3 | 熔点(℃) |
40 | 0 | 甲基 | Br | H | 正戊基 | 油 |
41 | 0 | 甲基 | 异丙基 | H | 甲基 | |
42 | 2 | Cl | H | H | 甲基 | 油 |
43 | 2 | -CH=CH-CH=CH- | H | 甲基 | 油 | |
44 | 0 | 甲基 | Br | 正丙基 | 甲基 | |
45 | 0 | 甲基 | Cl | H | 甲基 | |
46 | 0 | 甲基 | I | H | 甲基 | 102 |
47 | 0 | 甲基 | Br | 甲基 | 甲基 | |
48 | 0 | 甲基 | NO2 | H | 甲基 | 77 |
49 | 0 | 甲基 | 甲氧基 | H | 甲基 | 135-137 |
实施例50
5-溴-6,6′-二甲基-2,2′3′,4′-四甲氧基-二苯甲酮的制备
50A 6-甲基-2-甲氧基苯甲酸
6-甲基-2-甲氧基苯甲酸乙酯(642.0g,3.3摩尔)、水(2.5l)、乙醇(4.0l)和氢氧化钠(270g,6.6摩尔)的混合物回流加热并搅拌20小时。然后,蒸馏除去乙醇,反应混合物用水稀释并用浓盐酸酸化。真空吸滤收集固体物,用水洗并干燥,获得灰白色晶体460.0g(83.9%)。
50B 5-溴-6-甲基-3-甲氧基苯甲酸
在10至15℃下,将溴(102ml,2.0摩尔)和乙酸(225ml)的混合物加入50A(304.0g,1.8摩尔)、乙酸钠(164.0g,2.0摩尔)和乙酸(3.0l)的混合物中。反应混合物在室温下搅拌16小时。真空过滤收集固体物,用水洗并干燥,获得灰白色晶体321.0g(72.6%,熔点为81-83%)。
50C 5-溴-6,6′-二甲基-2,2′,3′,4′-四甲氧基-二苯甲酮
使50B(240g,1.0摩尔)与3,4,5-三甲氧基二甲苯(182g,1.0摩尔)在P2O5(1.0kg)和二氯乙烷存在下如实施例6所述的那样进行,获得白色晶体220g(54%,熔点89-91℃)。
上述实施例50A和50B中的皂化(和氢氧化钠)和溴化步骤分别颠倒成上述实施例6B和6A。
实施例50B和6A中所述的溴化步骤分别和游离酸和酯进行。反应条件也不一样,例如实施例50B中采用了极性质子溶剂(乙酸)和缓冲盐(乙酸钠)。而实施例6A采用非极性非质子溶剂(四氯甲烷)。
实施例51
6,6′-二甲基-5-氟-2,2′,3′,4′-四甲氧基二苯甲酮的制备
51A 2-叔丁基-4-氟-5-甲基苯酚
使4-氟-3-甲基苯酚(12.60g,0.1摩尔)、叔丁基氯(25ml)和FeCl3的混合物加热回流16小时。蒸馏除去过量的叔丁基氯,残余物用柱层析(石油醚∶乙酸乙酯,95∶5v/v)纯化,得到黄色油状纯净产物15.3g(84%)。
51B 6-溴-2-叔丁基-4-氟-5-甲基苯酚
将51A(0.91g)、四氯甲烷(20ml)、N-溴丁二酰亚胺(0.89g)和AlCl3的混合物在室温下搅拌3天。过滤并浓缩反应混合物。可使用得到的黄色油(1.25g)而不需进一步纯化。
51C 2-溴-4-氟-3-甲基苯酚
将51B(18.5g)、苯(18.5g)和AlCl3(6.5g)的混合物加热回流5小时。将反应混合物冷却至室温并用乙酸乙酯和水稀释。分离有机相并浓缩。残余物用柱层析(石油醚∶乙酸乙酯,95∶5v/v)纯化,得到白色晶体的纯净产物9.0g(62%)。
51D 2-溴-6-氟-3-甲氧基甲苯
将51C(9.0g)、碳酸钾(6g)、硫酸二甲酯(6g)和乙腈(150ml)的混合物加热回流1小时。将反应冷却物冷却至室温,并用水稀释,用***萃取两次。分离并浓缩有机相,可使用残余物(9.0g)而不需进一步纯化。
51E 3-氟-6-甲氧基-2-甲基苯甲酸
在-78℃下将正丁基锂的己烷溶液(18.1ml,2.5摩尔/升)缓慢加入51D(9.0g)和四氢呋喃(90ml)的混合物中。得到的反应混合物在-78℃下用二氧化碳饱和,并使其温热至室温。将反应混合物倒入水中,酸化并用***萃取两次。用氢氧化钠水溶液(5%)萃取有机相。对水性萃取液酸化,并用***萃取两次。干燥并浓缩有机相。可使用残余物(3.9g)而不需进一步纯化。
51F 6,6′-二甲基-5-氟-2,2′,3′,4′-四甲氧基二苯甲酮
如实施例6中所述的那样,使51E(3.9g,0021摩尔)与3,4,5-三甲氧基甲苯(3.85g;0.021摩尔)在P2O5(12.0g)和二氯甲烷(150ml)的存在下反应,得到白色晶体0.34g,熔点为58℃。
生物研究
A叶内吸性
小麦白粉病(WPM):
宿主:小麦(triticum aestivum L.)Kanzler种
病原体:禾白粉菌(Erysiphe graminis DC.)f.sp.tritici E.Marchal
测试步骤:
1.在暖房中将小麦种子(8/盆)种入直径为8cm的的塑料盆中。
2.当初生叶完全展开时,将每一盆中植物切到四个,其中两个在顶端叶表面叶顶芽下5cm处用永久性标记物作标记。这样每个盆中有两个处理区和两个未用处理区的植物。
3.用移液管将5μl配制的化合物施加到与标记物相对的叶子下表面区。施加区应盖住整个叶宽。在施用后,直至处理区变干才取出植物(半小时或以后)。
4.在经处理植物变干后,将它们移到暖房中放置2天,以使化合物离开。植物用底部浇水灌养植物。
5.施药两天后,在暖房中通过撒白粉病分生孢子来对植物接种。通常在接种后7-8天进行评价。
评价
通过评价各处理区叶子的三个区域的疾病来测定化合物传递的三种类型。
叶片转移(translaminar movement):根据疾病面积百分比来测定叶片转移区域(与施加区的叶子下表面直接相对的叶子上表面的标记区域;宽度约为5mm)。然后用下面的公式来计算叶片转移防病率:
远侧转移(distal movement)和近侧转移(proximal movement):按毫米数测定叶子表面远侧和近侧的无病区。远侧是指处理区到叶尖,近侧是指处理区到叶基。计算无病区相对于处理区到叶尖或到叶基整个距离的百分比。如果叶尖或叶基区域有可观察到的较轻微的疾病,也记录下来。
制剂和对照:
1.将化合物配制在含5%丙酮和0.05%吐温20的去离子水溶剂/表面活性剂体系中。用去离子水制备配制的化合物。化合物通常在400ppm下测试。
2.有两种对照:
用溶剂/表面活性剂溶液区域处理并接种的植物(溶剂空白)。
接过种的未经处理的植物(接种对照)。
这个评级结果列在表III中:
表III 叶内吸性
实施例 | 近侧转移(到处理区的距离)(mm) | 远侧转移(到处理区的距离)(mm) | 叶片转移活性(%) |
110 | 106 | 5046 | 100100 |
标准1标准2 | 48 | 528 | 100100 |
用曾用于EP 0 727 141的化合物作为标准,化合物如下:
标准1 2,6-二氯-6′-甲基-2′,3′,4′-三甲氧基二苯甲酮
标准2 2′,3′4′-三甲氧基-2,6,6′-三甲基二苯甲酮
B-1 2-甲氧基-二苯甲酮与2,6-二氯-及2,6-二甲基-二苯甲酮的杀真菌活性的比较
测试疾病:
(a) 小麦白粉病(WPM):
宿主: 小麦(Triticum aestivum L.)Kanzler种
病原体: 禾白粉菌(Erysiphe graminis DC.)f.sp.tritici E.Marchal
(b) 大麦白粉病(BPM):
宿主: 大麦(Hordeum vulgare L.)Golden Promise种
病原体: 禾白粉菌(Erysiphe graminis DC.)f.sp.hordei E.Marchal
测试步骤:
该测试是防治小麦和大麦白粉病按天计保护剂测试(zero day protectant test)。
1.将小麦或大麦种子(约8-10/盆)种入直径为6cm的塑料盆中并维持在暖房中。
2.当初生叶完全展开时,用顶部履带式单嘴喷灌(single nozzle overhead tracksprayer)以200升/公顷的用量喷洒配制的测试化合物。
然后风干植物。
3.在施加化合物后约3小时后接种。植物放在暖房长凳上,底部有浇水垫(water mat),通过撒白粉病感染的植物的分生孢子(10-14天的储藏培养物)对植物接种。
4.接种后约7天后根据有疾病症状/病征的叶面积的百分比来评价初生叶上的疾病。不对叶尖和叶基进行评价。然后用下面的公式来计算疾病防治率:
制剂、参比化合物和对照:
1.将工业品化合物配制在含5%丙酮和0.05%吐温20的去离子水的溶剂/表面活性剂体系中。化合物在加入水中之前先溶解在丙酮中;吐温20可通过丙酮或水加入。用溶剂/表面活性剂体系来稀释。测试化合物通常在覆盖几个重要级别浓度下进行测试,然后计算ED值来与化合物比较。
配制的化合物用去离子水来制备。
2.有两种对照:
用溶剂/表面活性剂溶液处理并接种的植物(溶剂空白)。
未经处理的接过种的植物(接种对照)。
这个评价的结果列在表IV中:
表VI 2-甲氧基二苯甲酮的杀真菌活性(ED90值)
2-甲氧基-二苯甲酮与2,6-二氯和2,6-二甲基二苯甲酮的杀真菌活性比较
0天保护剂测试的结果,其中对所有类似物进行了平行的测试
疾病 | 标准1 | 标准2 | ED90(ppm)2-甲氧基二苯甲酮的实施例 | 对照Quinoxyfen | |||||
1 | 4 | 6 | 7 | 10 | 45 | ||||
WPMBPM | 2824 | 208 | 46 | 57 | 0.10.9 | 76 | 78 | 0.1<0.1 | 1226 |
施加的化合物是配制在0.5%丙酮、0.05%吐温20的水中的工业品
B-2 2-甲氧基-二苯甲酮与2,6-二氯-及2,6-二甲基-二苯甲酮的药效和残留杀真菌活性的比较
测试疾病:
(a) 小麦白粉病(WPM):
宿主: 小麦(Triticum aestivum L.)Kanzler种
病原体: 禾白粉菌(Erysiphe graminis DC.)f.sp.tritici E.Marchal
(b) 黄瓜白粉病(QPM):
宿主: 黄瓜(Cucumis satrvus L.)Bush pickle种
病原体: 二孢白粉菌(Erysiphe cichoracearum DC)
测试步骤:
该测试步骤是测试白粉病的药效和残效防治。
1.将小麦种子(约8-10/盆)或黄瓜种子(1颗种子/盆)种入直径为6cm的塑料盆中并栽培于暖房。
2.当初生叶(小麦)或绒毛叶(黄瓜)完全展开时,用顶部履带式单嘴喷灌(single nozzle overhead track sprayer)以200升/公顷的用量喷洒配制的测试化合物。
然后风干植物。
3.对药效评价,接种在处理前2天后进行,而对残效防治评价,接种在处理后3天后进行。接种是将植物放在暖房长凳上,底部有浇水垫(water mat),通过撒白粉病感染的植物分生孢子(10-14天龄的储藏培养物)来对植物接种。在接种与进行药效评价和残效评价的处理中间,植物放在暖房中并保持底部浇水。
4.接种后约7天后,根据有疾病症状/病征的叶面积百分比来评价初生叶(小麦)或绒毛叶(黄瓜)上的疾病。在小麦例子中,不对叶尖和叶基进行评价。然后用下面的公式来计算疾病防治率:
制剂、参比化合物和对照:
1.将工业品化合物配制在含5%丙酮和0.05%吐温20的去离子水的溶剂/表面活性剂体系中。化合物在加入水中之前先溶解在丙酮中;吐温20可通过丙酮或水加入。用溶剂/表面活性剂体系来稀释。
用去离子水制备配制的化合物。
2.有两种对照:
用溶剂/表面活性剂溶液处理过并接过种的植物(溶剂空白)。
未经处理的接过种的植物(接种对照)。
这个评价的结果列在表V中:
表V 2-甲氧基二苯甲酮的治愈活性和残余杀真菌活性
疾病测试 | 用量(ppm) | 疾病防治(%效率) | 2-甲氧基二苯甲酮实施例 | ||||
标准1 | 标准2 | 1 | 6 | 4 | 7 | ||
测试 | A | B | A/B | A/B | B | C | |
WPM2 da C | 125012512,5 | 796031 | 927455 | 88/8579/6569/52 | 98/8795/8990/61 | 617155 | 979373 |
WPM3 da R | 125012512,5 | 1008375 | 1008170 | 100/100100/10090/100 | 100/100100/100100/100 | 10010099 | 10010099 |
QPM3 da R | 125012512,5 | 10000 | 89614 | 100/1005/612/3 | 100/10092/922/35 | 100978 | 100892 |
2 da C=2天治药效 在施加前2天接种
3 da R=3天残药效 在施加后3天接种
Claims (11)
2.根据权利要求1所述的方法,其中极性质子溶剂选自脂族酸和脂族醇。
3.根据权利要求2所述的方法,其中极性质子溶剂是乙酸。
4.根据权利要求1所述的方法,其中溴用量为相当于起始化合物VI为1.05-1.2摩尔当量。
5.根据权利要求1所述的方法,其中化合物VI与溴的反应在弱碱或缓冲体系存在下进行。
7.根据权利要求6所述的方法,其中极性质子溶剂选自脂族酸和脂族醇。
8.根据权利要求7所述的方法,其中极性质子溶剂是乙酸。
9.根据权利要求6所述的方法,其中溴用量为相当于起始化合物VI为1.05-1.2摩尔当量。
10.根据权利要求6所述的方法,其中化合物VI与溴的反应在弱碱或缓冲体系存在下进行。
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