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CN1159278C - 杀真菌方法、化合物和含二苯甲酮的组合物 - Google Patents

杀真菌方法、化合物和含二苯甲酮的组合物 Download PDF

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Publication number
CN1159278C
CN1159278C CNB961010142A CN96101014A CN1159278C CN 1159278 C CN1159278 C CN 1159278C CN B961010142 A CNB961010142 A CN B961010142A CN 96101014 A CN96101014 A CN 96101014A CN 1159278 C CN1159278 C CN 1159278C
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CN
China
Prior art keywords
chloro
group
compound
methyldiphenyl ketone
methoxyl group
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Expired - Fee Related
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CNB961010142A
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English (en)
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CN1134929A (zh
Inventor
�ڶ������´�
于尔根·柯茨
͢��H��G��³����
克里斯廷·H·G·鲁道夫
路德维格·施罗德
吉多·艾伯特
Ee
安奈罗斯·E·E·雷尼格
G���ֶ�����
埃瓦尔·G·西林定
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Wyeth Holdings LLC
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American Cyanamid Co
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Priority claimed from US08/479,502 external-priority patent/US5679866A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of CN1134929A publication Critical patent/CN1134929A/zh
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    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
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    • A01N33/18—Nitro compounds
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    • A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
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    • 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
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    • 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
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    • 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
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    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
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    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
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Abstract

本发明提供一种控制植物病原体性真菌和由此引起疾病的方法，它包括使上述真菌与有效杀真菌量的具有式I所示结构的二苯甲酮类化合物接触，本发明还提供对保护植物免受植物病原体性真菌和真菌性疾病侵害有用的杀真菌剂即式Ia所示二苯甲酮类化合物及其组合物。

Description

杀真菌方法、化合物和含二苯甲酮的组合物
为了满足不断增长的人口对食物的可供性、营养性和货架寿命的要求，食品生产依靠各种农业技术。杀真菌剂是全球有效的这些农业技术中的一种。杀真菌剂是农业化学物质，可使作物和食物免受真菌和真菌疾病的侵害。作物和食物经常受到各种真菌类微生物的威胁，如不加以控制，会引起作物毁坏和欠收。
特别是子囊菌，是一种尤其对谷物和果物始终存在威胁的白粉粉病的致病菌。然而，以控制病害的用量使用杀真菌剂，会给目标植物带来植物毒性损害。
因此，本发明的目的在于提供一种控制植物病原体性真菌而不会对宿主植物产生并存的植物毒性损害的方法。
本发明的另一个目的在于提供一种有效安全地保护重要农作物免受植物病原体性真菌的感染和由此引发的病害所致的侵害和损失的方法。
本发明的还有一个目的是提供二苯甲酮类杀真菌剂和含二苯甲酮类化合物的杀真菌组合物。
本发明的上述及其他目的和特征将在下述详细描述中变得清晰明了。
本发明提供一种控制植物病原体性真菌和由此引起的病害的方法，包括使上述真菌与有效杀真菌量的具有式I所示结构的二苯甲酮类化合物接触，
Figure C9610101400091
式中，R1表示卤原子、可任意取代的烷基或烷氧基、氰基或硝基；m为0或整数1、2、3或4；R2独立地表示卤原子、可任意取代的烷基或烷氧基、硝基或当R1和R2与两个邻近碳原子相连时，R1和R2可一起表示-CH＝CH-CH＝CH-或可任意取代的亚烷基或氧亚烷氧基，如O-CF2-O；R3表示氢原子、卤原子、可任意取代的烷基、烷氧基、链烯基、烷硫基、烷基亚磺酰基、烷基磺酰基、氰基、羧基、羟基、硝基或可任意取代的氨基；R4表示氢原子或可任意取代的烷基或酰基；R5表示氢原子、卤原子、可任意取代的的烷基、烷氧基、链烯氧基、炔氧基、烷硫基、环烷基、环烷氧基、硝基、羟基、苯氧基、三烷基硅氧基、-ONa、-OK、-OC(O)R7、-OCHR8C(O)R7、-OC(O)NR8R9、-OS(O)2R8、-OS(O)2NR8R9、-OP(X1)(OR8)OR9、-OP(X1)(R8)R9、-S(O)R8、-S(O)2R8或R4和R5可一起表示可任意取代的亚烷基或亚烷氧基链；n表示0或整数1或2；R6独立地表示卤原子、可任意取代的烷基、链烯基、炔基、烷氧基、链烯氧基、炔氧基、环烷基、环烷氧基、羟基、-OC(O)R10基团、或当R5和R6与两个邻近的碳原子相连时，R5和一个R6可一起表示-CH＝CH-CH＝CH-或可任意取代的氧亚烷氧基链；R7表示氢原子或可任意取代的烷基、烷氧基或芳基；R8、R9和R10独立地表示氢原子、烷基、芳基或芳烷基，或R8和R9可一起表示可任意地被氧或氮原子中断的亚烷基链；X表示氧原子、硫原子或基团NOR；X1表示氧或硫原子；Y表示氧或硫原子或磺酰基、亚磺酰基；R表示氢原子或可任意取代的烷基、芳烷基、芳基或酰基。
在本说明书和权利要求书中，“二苯甲酮”一词的含义包括二苯甲酮的肟衍生物(X＝NOR)、二苯硫酮(X＝S)和未衍生的酮二苯甲酮。
本发明还提供保护作物的方法、具有式Ia所示结构的杀真菌的二苯甲酮类化合物、制备上述二苯甲酮类化合物和至少含有一个具有式I或Ia所示结构的化合物以及农业上可接受的载体的组合物。
由真菌感染和侵扰引发的重要农作物和园艺作物的欠收和损害已导致巨大的经济损失。控制病虫害的战略、田间抗病性、病毒性菌株均成为农业工作者在防治植物病原体性真菌疾病方面所关注的对象。尤其是子囊菌，作为白粉病的致病菌，仍然是谷物和水果生产中的一大问题。而且，使用各种杀真菌剂往往会同时产生对宿主植物的损害。
业已发现，式I的二苯甲酮类化合物是高效杀真菌剂，尤其对控制霉病如白粉病有效。在控制真菌的方法中有用的式I的化合物是具有下述结构的二苯甲酮类化合物：
式中，X、Y、R1、R2、R3、R4、R5、R6、m和n的定义同上。
作为取代基，或作为其他取代基如烷氧基或烷硫基的一部分的烷基，可以是直链的，也可以是支链的，可以含多至18个碳原子，较好的是宜在14个以内，最好不超过10个碳原子，具体例子包括：甲基、乙基、丙基、丁基、戊基、己基等以及它们的异构体，如异丙基、异丁基、叔丁基、异戊基等。低级烷基或烷氧基含1～10个碳原子。作为取代基或其它取代基的一部分的环烷基部分宜含3-10个，最好3～6个碳原子。链烯基或炔基宜含2～6个，最好2～4个碳原子，例如乙烯基、丙烯基、烯丙基、丁烯基等以及含一个以上双键的链，如戊二烯基等。亚烷基宜含1～5个，最好1～4个碳原子。
从形式上而言，通过从羧基中除去羟基便形成酰基，在本发明中使用的酰基包括甲酰基和可任意取代的烷羰基、芳羰基。
卤原子表示氟、氯、溴和碘，以氯为佳。较佳的卤代烷基部分宜为二氟甲基和三氟甲基。
可任意取代的部分可以是未取代的，也可以是有一至化学上最大可能数目的取代基。任意的取代基可以是生物杀灭物质的开发和/或改良这些物质以改变它们的活性、持久性、渗透性和任何其它特性的过程中通常使用的任一种取代基。这些取代基的具体例子包括卤原子，尤其是氟、氯或溴，硝基、氰基、羟基、羧基、氨基、烷基-或芳烷基氨基、二烷基氨基、环烷基氨基、哌啶基、哌啶子基、吗啉基、氨基甲酰基、芳基或苄基氨基甲酰基、一或二烷基氨基甲酰基、吗啉基羰基、三烷基硅烷基、烷基、链烯基、炔基、烷氧基、烷氧烷基、烷氧烷氧基、环烷基、环烷氧基、酰基、可任意取代的苯甲酰基、苯并噁唑基、烷氧羰基、可任意取代的吡啶基、苯氧基或萘基、苯基或被选自卤原子、烷基、烷氧基、烷氧烷基、烷氧烷氧基、烷硫基、苯硫基、苄硫基、芳烷氧基、羟基、羧基、烷酯基、氰基中的一或多个取代基取代的苯基、可任意取代的氨基、硝基、三氟甲基、三氟甲氧基等。这些任意的取代基的烷基部分可以含1～6个碳原子，最好含1或2个碳原子。若这里所述的被取代的基含两或多个取代基，这些取代基可以是相同的，也可以是不同的。
式I的二苯甲酮类化合物呈油状或胶状，但绝大多数为晶状固体物质，具有有用的杀真菌特性。例如，它们可用于农业或相关领域，如园艺业和葡萄裁培业，以控制植物病原体性真菌，尤其是子囊菌，以及白粉病如(学名)Erysiphe gramiris、Podosphaeraleucotricha、Uncinula necator等。这些二苯甲酮类化合物在一个宽的浓度范围内具有较强的杀真菌活性，可用于农业而没有有害的植物毒性效果。
在本发明的方法中有用的式I的化合物的较佳例为取代基具有下述定义的化合物：R1表示卤原子或可任意取代的烷基或烷氧基；m表示0或整数1、2或3；R2独立地表示卤原子或可任意取代的烷基或烷氧基；或R1和R2一起表示-CH＝CH-CH＝CH-、氧亚烷氧基、氧二氟亚甲氧基或亚烷基；R3表示卤原子、可任意取代的烷基、链烯基、烷硫基或烷基磺酰基、硝基或可任意取代的氨基；R5表示氢原子、可任意取代的烷基、烷氧基、链烯氧基、炔氧基、环烷氧基或烷硫基、羟基、三烷基硅氧基、或-OC(O)R7、-OCHR8C(O)R7、-OC(O)NR8R9、NH-CO-R7、-OS(O)2R8或-OS(O)2NR8R9基团；或R4和R5一起表示可任意取代的亚烷氧基；n表示O或整数1；R6表示可任意取代的烷基、链烯基、炔基、烷氧基、链烯氧基、炔氧基、环烷基或环烷氧基、-OC(O)R10基团；R7表示氢原子或烷基、烷氧基；X表示氧原子或NOR基团；R表示氢原子或可任意取代的烷基。
用有效杀真菌量的取代基具有下述定义的式I化合物可很好地控制植物病原性真菌：R1表示卤原子或可任意取代的低级烷基；m表示整数1或3；R2独立地表示卤原子或可任意取代的低级烷基；R3表示卤原子、可任意取代的烷基或链烯基、或可任意取代的氨基；R5表示可任意取代的烷基、烷氧基、链烯氧基、炔氧基、环烷氧基或烷硫基或R4和R5可一起表示可任意取代的亚烷氧基；n表示0或整数1；R6表示可任意取代的烷基、链烯基、炔基、烷氧基、链烯氧基、炔氧基、环烷基或环烷氧基、-OC(O)R10基团；R7表示烷基或烷氧基；X表示氧原子或NOR基团；Y表示氧原子；R表示氢原子或C1～C4烷基。
取代基具有下述定义的式I化合物尤佳：R1表示卤原子或C1～C4烷基；R2独立地表示卤原子或C1～C4烷基；R3表示卤原子或可任意取代的C1～C4烷基；R4表示可任意取代的C1～C4烷基；R5表示可任意取代的低级烷基、烷氧基、链烯氧基、炔氧基或环烷氧基；R6表示可任意取代的C1～C6烷氧基、链烯氧基、炔氧基或环烷氧基。
用有效杀真菌量的一或多个下述化合物可有效控制植物病原体性真菌：
2，3，5，6-四甲基-4′，5′，6′-三甲氧基-2′-甲基二苯甲酮；
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮-O-甲肟；
2，6-二氯-5′-叔丁氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′，6′-二正丁氧基-4′-甲氧基-2′-甲基二苯甲酮；
2′-烯丙基氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-苄氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-丁氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-环己基甲氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-苯甲酰氧基甲氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-环戊基氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′3′，4′-三甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′-乙氧基-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′-庚氧基-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′-己氧基-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-2′-(2-甲氧基-乙氧基)-6′-甲基二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-(3-甲基丁氧基)二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-(丙-2-炔基氧基)二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-戊氧基二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-丙氧基二苯甲酮；
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-(3-甲基丁氧基)二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-(丙-2-炔基氧基)二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-(辛氧基)二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-(戊氧基)二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-丙氧基二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-三甲基硅烷基甲氧基二苯甲酮；
2，6-二氯-5′-(1-乙基-丙氧基)-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-二氟甲氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-乙氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-庚氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-己氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮-O-正丙肟；
2，6-二氯-5′-异丁氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-异丙氧基-4′-甲氧基-2′-甲基二苯甲酮；
5′-丁氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环己基甲氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环己基氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环戊基氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环丙基甲氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；或
5′-癸氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
式IB的化合物具有特别的杀真菌用途。
Figure C9610101400151
式中，Q表示氢或氯原子；R表示氢原子、C3～C8环烷氧基或可被一或多个氟原子、或一个苯基、苯氧基、苯硫基或苄氧基任意取代的C1～C8烷氧基，其中的苯基部分可被卤原子、C1～C4烷基、C1～C4烷氧基、三氟甲基或三氟甲氧基取代；R′表示氢或可被一或多个卤原子、C1～C4烷氧基、苯基、苯氧基或苯硫基取代的C1～C10烷基，其中的苯基部分可被卤原子、C1～C4烷基、C1～C4烷氧基、三氟甲基或三氟甲氧基取代；条件是：当Q和R表示氢时，R′不可以是甲基。
取代基具有下述定义的式IB化合物尤佳：
式中，Q表示氢或氯原子；R表示氢原子、C5～C7环烷氧基、可被一或多个氟原子或一个苯基、苯氧基、苯硫基或苄氧基任意取代的C1～C6烷氧基，其中的苯基部分可被卤原子、甲基、甲氧基、三氟甲基或三氟甲氧基任意取代，R′表示氢或可被氟、氯、C1～C4烷氧基、苯基、苯氧基或苯硫基任意取代的C1～C8烷基，其中的苯基部分可被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基取代。
具有特别价值的化合物还有式IC化合物。
式中，Q和Q′独立地表示氢原子或甲基；R表示氢原子、C3～C8环烷氧基或可被一或多个氟原子、苯基、苯氧基、苯硫基或苄氧基任意取代的C1～C8烷氧基，其中的苯基部分可被一或多个卤原子、C1～C4烷基、C1～C4烷氧基、三氟甲基或三氟甲氧基取代；R′表示氢或可被一或多个卤原子、C1～C4烷氧基、苯基、苯氧基或苯硫基任意取代的C1～C10烷基，其中的苯基部分可被一或多个卤原子、C1～C4烷基、C1～C4烷氧基、三氟甲基或三氟甲氧基取代。
取代基具有下述定义的式IC化合物尤佳：
Q和Q′独立地表示氢原子或甲基，R表示氢原子、C5～C7环烷氧基或可被一或多个氟原子、一个苯基、苯氧基、苯硫基或苄氧基任意取代的C1～C6烷氧基，其中的苯基部分可被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基取代；R′表示氢或可被一或多个氟、氯、C1～C4烷氧基、苯基、苯氧基或苯硫基任意取代的C1～C8烷基，其中的苯基部分可被一或多个溴、甲基、甲氧基、三氟甲基或三氟甲氧基取代。
本发明还提供式Ia表示的新型二苯甲酮类化合物
式中，R1表示卤原子、可任意取代的烷基或氰基；m为整数2、3或4；R2独立地表示卤原子、可任意取代的烷基或烷氧基或当R1和R2与两个邻近碳原子相连时，R1和R2可一起表示-CH＝CH-CH＝CH-或可任意取代的亚烷基或氧亚烷氧基；R3表示氢原子、卤原子、可任意取代的烷基、烷氧基、链烯基、烷硫基、烷基亚磺酰基、烷基磺酰基、氰基、羧基、羟基、硝基或可任意取代的氨基；R4表示可任意取代的烷基或酰基；R5表示卤原子、可任意取代的烷氧基、链烯氧基、炔氧基、烷硫基、环烷基、环烷氧基、三烷基硅氧基、-ONa、-OK、-OC(O)R7、-OCHR8C(O)R7、-OC(O)NR8R9、-OS(O)2R8、-OS(O)2NR8R9、-OP(X1)(OR8)OR9、-OP(X1)(R8)R9、-S(O)R8、-S(O)2R8或R4和R5可一起表示可任意取代的亚烷基或亚烷氧基链；n表示0或整数1或2；R6独立地表示可任意取代的烷氧基、羟基、-OC(O)R10基团、或当R5和R6与两个邻近的碳原子相连时，R5和一个R6可一起表示-CH＝CH-CH＝CH-或可任意取代的氧亚烷氧基链；R7表示氢原子或可任意取代的烷基、烷氧基或芳基；R8、R9和R10独立地表示氢原子、烷基、或R8和R9可一起表示可任意地被氧或氮原子中断的亚烷基链；X表示氧原子、硫原子或基团NOR；X1表示氧或硫原子；Y表示氧或硫原子或磺酰基、亚磺酰基；R表示氢原子或可任意取代的烷基、芳烷基、芳基或酰基；条件是：当X表示氧或硫原子且
(1)当R1表示卤原子时，(R2)m不可以是卤原子或是至多一个烷基或烷氧基；
(2)当R1表示烷基时，R2不可以是烷基；
(3)当m为1时，R3不可以是烷氧基；
(4)当R3表示链烯基时，R3不可以被烷氧基或酰基取代；
(5)当R3表示卤代烷基时，R1和R2不可以是卤代烷基；
(6)当Y表示氧原子时，R3和R6不可以是氢原子且n必须是1或2。
式I化合物可用通常的方法制备。
因此，式I化合物(包括式Ia化合物)可通过包含使式II化合物与式III化合物进行反应的方法来制备，
Figure C9610101400181
式中，R1、R2、R3、R4、R5、R6、Y、m和n的定义同前，Z1和Z2中的一个表示氢原子，另一个表示基团COCl；或一个表示卤化镁基团MgHal，其中的Hal表示卤原子，以溴、碘为佳，另一个表示COCl或醛基、腈基，当为最后二种情况时，再随后分别进行氧化或水解，或任意地再进一步衍生化。
式II和III的起始物质是已知产品，故可以用已确立的方法或它们的常规的修改法来制备。与选择的反应条件不相适应的取代基R1至R9可在二苯甲酮形成后导入。它们可通过已知方法如随后的衍生化或合适基团的取代或切除合适的保护基来产生。
当Z1和Z2中的一个为氢，另一个为COCl时，上述方法是弗瑞德-克来福特反应，可在路易斯酸催化剂的存在下，按已确立的步骤进行。合适的催化剂包括FeCl3、AlCl3、SnCl4、ZnCl2、TiCl4、SbCl5和BF3，催化剂可以是等摩尔当量的(以酰基卤为基准)。然而，在高的温度下，合适的是在回流温度下，也可以使用较少量的催化剂，在这些条件下的优选的催化剂是FeCl3、I2、ZnCl2、铁、铜、强磺酸如F3CSO3H，和酸性离子交换树脂如Amberlyst_15和Nafion_。在约50～180℃下，优选的催化剂是FeCl3，摩尔比为0.001～0.2。反应可在惰性溶剂如氯化乙烯、二氯甲烷、苯、辛烷、癸烷中或在溶剂混合物中或无溶剂的条件下进行，其方便的做法是使用过量的一种反应剂，例如，以1∶5至5∶1的范围使用反应剂。如使用AlCl3，摩尔比宜为0.5～2，适宜的溶剂为二氯甲烷或氯化乙烯，温度通常在-10至-70℃。如在起始物质中、R3表示甲基且R6或一个R6表示5-烷氧基(式III)，可能发生醚的开裂，给出6-羟基化合物，该6-羟基化合物然后可用通常的方法加以衍生化。
如果式II化合物表示2，6-二氯苯甲酰氯而式III化合物为1，2，3-三烷氧基-5-烷基苯，以AlCl3为催化剂，根据反应条件，可用弗瑞德-克来福特反应制备不同的产物。在氯化铝的摩尔量为0.5～2、温度约为0～25℃、溶剂为例如二氯甲烷或氯化乙烯的情况下，在约1～20小时内，在式I化合物的6位(邻位)发生醚开裂；在更高的温度(约40℃)和如果需要，更长的反应时间(约2～24小时)，在5位(间位)也会发生醚开裂。
如果希望的话，下述方法可类似地用于其它起始物质。
由下式所示化合物出发，
式中，R1、R2宜为Cl、CH3、R表示H或O-烷基，烷基宜为甲基，在50～100℃和HBr/乙酸的条件下发生醚开裂，得下式所示化合物，
式中，R′表示H或OH。
由下式所示化合物出发，
Figure C9610101400203
式中，R1和R2的定义同前，在催化剂AlCl3(0.5～2摩尔)和二氯甲烷等惰性溶剂中，在约20～50℃，发生O-烷基开裂，得相应的OH化合物。
式VIII化合物、IX和由X得到的醚开裂产物的烷基化可按通常方法进行。
可在高的温度(例如60～150℃)下，在碱性化合物如碳酸钾的存在下，于低级醇中，使R′为H的式IX化合物与烷基卤(烷基部分可有取代基)反应。
当羟基在其它位置(如在VIII中，R′＝OH或在由X得到的反应产物中)时，必须使羟基化合物与例如氢氧化钾反应得到金属盐。然后将该盐在无水条件下，于极性溶剂(例如二甲基甲酰胺)中与可被任意取代的烷基卤反应。
由相应的二碱金属盐(最好为二钠盐，由二羟基化合物与氢化钠在惰性溶剂如四氢呋喃中反应而制得)出发，再将该盐在惰性极性溶剂(例如二甲基甲酰胺)中与过量的可任意取代的烷基卤于约80～120℃的温度下反应，可用相同的可任意取代的烷基进行R′为OH的式IX化合物的二烷基化。
用式Hal-(CH2)n-Hal(Hal＝Cl、Br或I；n＝1-4)表示的二卤代化合物进行的二烷基化导致环化(化合物XI；n的定义同前)：
Figure C9610101400211
在过量碳酸钾和小量的作为催化剂的氧化铜的存在下，于约10～50℃，最好在室温下进行二羟基化合物IX(R′＝OH)与二卤代化合物的反应。
为制备酰基化物，将相应的羟基化合物，例如式XII化合物
(式中，R1和R2表示Cl和CH3)以其盐(例如钾盐)的形式在惰性极性溶剂如二甲基甲酰胺中与可任意取代的酰基氯在约10～50℃反应。
式IX化合物(式中，R′＝H)的酰基化可通过在惰性溶剂中，或无惰性溶剂的情况下将该化合物与酸酐于约80～120℃加热来进行。
为制备式XIII化合物，
Figure C9610101400222
(式中，R表示叔丁氧基，R1和R2的定义同前，但优选Cl)将相应的羟基化合物(XIII；R＝OH)溶于惰性溶剂中，然后将溶液冷却至-70℃，再加入催化量的三氟甲磺酸，住混合液中吹入2-甲基丙烯气流2～6小时。将酸中和后，可分离出生成的叔丁氧基化合物。
式XIV所示的5-硝基化合物(R＝NO2)
Figure C9610101400231
可通过用浓(65％)硝酸在约50～100℃将5位上未取代的相应化合物(R＝H)硝化来制备。
用浓(65％)硝酸在约30～60℃的条件下，可进行式XV化合物的2位硝化。
Figure C9610101400232
在高的温度(60～100℃)下，于水/乙酸(50∶1)的混合液中，用过量的铁粉可将生成的或另法制备的硝基化合物还原成相应的氨基化合物，例如式XVI化合物。
Figure C9610101400233
用过量的甲酸与此氨基化合物在回流温度下反应，导致氨基化合物甲酰化。
式XIV化合物(R＝H)的5位溴化可通过在10～30℃下，往该化合物在三氯甲烷中的溶液里滴加等摩尔量的溴(例如，在三氯甲烷的溶液中)来进行。
在惰性溶剂中，于回流温度下将相应的二苯甲酮类化合物与五硫化二磷加热2～10小时，可由相应的二苯甲酮类化合物制备二苯硫酮类化合物(I；X＝S)。
当将有机卤化镁与腈反应时，即，其它基团Z1或Z2(式II、III)表示CN时，瞬间反应产物为式IV表示的亚胺：
适当地使用无机酸如盐酸或硫酸进行酸水解，可容易地将该中间体转化成目的产物即X为氧原子的式I所示的二苯甲酮衍生物。
当有机卤化镁与醛反应时，即，其它基团Z1或Z2表示CHO时，瞬间反应产物为式V表示的叔醇：
Figure C9610101400242
适当地在催化剂的存在下，使用Mn(IV)、Mn(VII)、Ce(IV)或Cr(VI)衍生物、硝酸或氧进行氧化，可容易地将该式V所示中间体转化成目的产物即IX为氧原子的式I所示二苯甲酮类化合物。
在氯化铝存在下，通过于惰性溶剂中使有适当取代的式VI所示腈氧化物(氧腈)与合适的式VII所示的邻二甲氧基苯反应，生成中间体，再在酸水溶液中水解该中间体，生成目的产物化合物IB，从而可制备式I化合物的一些肟衍生物。反应示于下列流程图1中。
                     流程图I
Figure C9610101400251
在式Ib所示化合物中，取代基R1、R2、R3、R6和n的定义与在上述式I和Ia中的相同，m表示0或整数1、2或3。通过使用惯用的烷基化和酰基化技术，可将式Ib表示的肟进行O-烷基化或O-酰基化。
按已确立的方法或它们的常规改良法如氢化、酰基化、醚键开裂、烷基化或硝化，可将按本发明的方法制得的二苯甲酮类化合物的取代基进一步加以衍生。
本发明的式Ia化合物是优异的杀真菌剂，尤其是可在农业或相关领域用于控制植物病原体性真菌。它们可用于控制白粉病，尤其是Erysiphe graminis、Podosphaera leucotricha或Uncinula necator.由于植物具有优异的耐药性，故对于不希望被可控制的真菌感染的所有植物裁培物均可使用上述化合物，例如，可用于小粒谷类作物、苹果树、葡萄树。在控制真菌剂量水平上，对目标作物没有植物毒性是本发明的一个特征。
本发明还提供一种杀真菌组合物，它包括具有前述定义的式I或Ia所示化合物和农业上可接受的载体，该组合物可含一或多个本发明的化合物。本发明组合物中的至少一个载体宜为表面活性剂。例如，组合物可含至少两个载体，它们中的至少一个是表面活性剂。
式I或Ia表示的化合物可以工业品施用，然而，这些物质最好作为组合物施用，所述组合物除了式I或Ia化合物外，还包含制成制剂时使用的助剂和辅剂，通过已确立的方法制成例如浓缩乳液、可直接喷洒或可被稀释的溶液、稀释过的乳液、可湿性粉剂、可溶性粉剂、粉末剂、颗粒剂、微胶囊。与组合物(剂型)一样，施用方式如喷洒、喷雾、散布、泼浇可根据所需目的和所处环境而定。
可以预期，式I或Ia化合物可制成制剂或单独、或与一或多种农药或植物生长调节剂一起施用。组合使用的农药可以是除草剂、杀虫剂或其它杀真菌剂或它们的组合物。当式I或Ia化合物与另一种或多种农药合用时，它们可以同时使用或前后使用。可与式Ia化合物合用的杀虫真菌剂的例子有4，6-二硝基邻甲苯酚、benalaxyl、苯菌灵、敌菌丹、克菌丹、多菌灵、百菌清、铜、cymoxanil、抑菌灵、二氯萘醌、difenoconazole、dimethomorph、diniconzole、敌螨普、二噻农、fenpicloril、fenpropiomorph、土菌消、imazalil、iprodione、二氯苯基甲乙基二氧咪唑烷羧酰胺、富士一号、春雷霉素、代森锰锌、mepronil、黄色氧化汞、oxadixyl、噁喹酸、penconazole、甲基代森锌、pyrifenox、涕必灵、福美双、tolclofos-methyl、三唑二甲酮、triflumizole、嗪氨灵、有效霉素A、vinclozolin、代森锌、福美锌等。
本发明的杀真菌组合物可用已确立的方法如将活性成分与其它物质如填充剂、溶剂、固体载体和任意的表面活性化合物(表面活性剂)进行彻底混合和/或研磨来制备。
溶剂可以是芳族烃，优选C8～C12馏分，例如二甲苯或二甲苯混合物、有取代的萘、苯二甲酸酯如苯二甲酸二丁酯或二辛酯、脂族烃，例如环己烷或石蜡、醇类和二元醇类似及它们的醚和酯如乙醇、乙二醇—和二甲醚、酮，例如环己酮、高极性溶剂如N-甲基-2-吡咯烷酮、二甲基亚砜、烷基甲酰胺、环氧化的植物油、例如环氧化的椰子油或豆油、水。
可用于粉末剂或可分散性粉剂的固体载体的例子有无机填充剂，如方解石、滑石、高岭土、蒙脱石、硅镁土。加入高分散的硅胶或聚合物可改善载体的物理特性。
用于颗粒剂的载体可以是多孔物质，如浮石、碎砖、海泡石、皂土、非吸附性载体如方解石或砂。另外，大量的预颗粒化的无机或有机物质如白云石或研碎的植物残渣也可以使用。
根据待制成制剂的二苯甲酮类化合物的性质，合适的表面活性物质的例子有具有良好分散、乳化和湿润特性的非离子型、阴离子型或阳离子型表面活性剂。表面活性剂也可以是表面活性物质的混合物。
合适的表面活性剂可以是所谓的水溶性皂以及水溶性合成表面活性化合物。皂通常是高级脂肪酸(C10～C20)的碱金属盐、碱土金属盐或可任意取代的铵盐，如油酸或硬脂酸的钠或钾盐、由例如椰子油或牛油制得的天然脂肪酸混合物的钠或钾盐。此外，还可以使用脂肪酸的甲基牛磺酸盐。但以所谓合成的表面活性剂为优选，尤其是脂族磺酸盐、脂族硫酸盐、磺化苯并咪唑衍生物和烷芳基磺酸盐。肪族硫酸盐或脂族磺酸盐一般以碱金属盐、碱土金属盐或可任意取代的铵盐供用，其烷基部分含8～22个碳原子，此烷基还表示酰基残基的烷基部分，如木质素磺酸钠或钙、或硫酸十二烷酯、由天然脂肪酸制得的脂肪醇混合物的钠或钙盐。还包括硫酸酯的盐、磺酸的盐和脂肪醇和环氧乙烷的加成物。磺化过的苯并咪唑衍生物宜含2个磺酸残基和一个C8～C22脂肪酸残基。烷芳基磺酸盐的例子有十二烷基苯磺酸、二丁基萘磺酸或萘磺酸和甲醛缩合物的钠、钙或三乙铵盐。此外，也可以使用磷酸盐，如对壬基苯酚-(4-14)-环氧乙烷加成物的磷酸酯或磷脂的盐。
非离子型表面活性剂优选脂族或环脂族醇、饱和的或非饱和的脂肪酸以及烷基酚的聚乙二醇醚衍生物，该聚合物含3～10个乙二醇醚基以及在(脂族)烃残基上含8～20个碳原子，在烷基酚的烷基残基上含6～18个碳原子。其它合适的非离子型表面活性剂是水溶性的、含20～250个乙二醇醚基团的环氧乙烷和聚丙二醇的多加合物、乙二氨基聚丙二醇和烷基部分含1～10个碳原子的烷基聚丙二醇，一般每个丙二醇单元含1～5个乙二醇单元的物质。非离子型表面活性剂的例子有壬基苯酚聚乙氧基乙醇类、蓖麻油聚乙二醇醚、环氧乙烷和聚丙烯的多加合物、三丁基苯氧基聚乙氧基乙醇、聚乙二醇、辛基苯氧基聚乙氧基乙醇。此外，也可以使用聚氧亚乙基脱水山梨糖醇的脂肪酸酯，如聚氧亚乙基山梨糖醇三油酸酯。
阳离子型表面活性剂优选含至少一个C8～C22烷基残基以及含可任意卤代的低级烷基、苄基或羟烷基残基的季铵盐。这些盐以卤盐、甲基硫酸盐或烷基硫酸盐为佳，例如硬脂基三甲基氯化铵或苄基二(2-氯乙基)乙基溴化铵。
通常用于本发明组合物的表面活性剂在例如下述出版物中已有揭示：
“MeCutheon′s Detergents and Emulsifiers Annual″，MCPublishing Corp.，Ridgewood，NJ，USA 1981；H.Stache，“Tensid-Taschenbuch”，2nd ed.，C.Hanser，Munich，Vienna，1981；
M.and J.Ash，″Encyclopedia of Surfactants″，vol.I-III，Chemical Publishing Co.，New York，NY，USA 1980-1981.
本发明的农药组合物可含0.1～95％，最好0.1～80％的至少一个式I或Ia化合物和1～99.9％的固体或液体辅剂以及0～25％，最好0.1～25％的表面活性剂。
本发明组合物的例子有：
浓缩乳液
活性成份         1～20％        优选5～10％
表面活性物质     5～30％        优选10～20％
液体载体         50～94％       优选70～85％
浓缩悬浮液
活性成分         5～75％        优选10～50％
水               94～24％       优选88～30％
表面活性物质     1～40％        优选2～30％
可湿性粉剂
活性成分         0.5～90％      优选1～80％
表面活性物质     0.5～20％      优选1～15％
固体载体         5～95％        优选15～90％
粉末剂
活性成分         0.1～10％      优选0.1～1％
固体载体         99.9～90％     优选99.9～99％
颗粒剂
活性成分          0.5～30％         优选3～15％
固体载体          99.5～70％        优选97～85％
作为商品，本发明的杀真菌组合物可能以浓缩型为宜，而终端用户一般使用稀释的组合物。上述组合物可稀释至活性成分浓度为0.001％。剂量通常在0.01～10公斤活性物质/公顷的范围内。
该组合物还可包含其他辅剂，如稳定剂、去泡沫剂、粘度调节剂、增稠剂、粘合剂、肥料或其他活性成分，以得到特殊效果。
为能更清晰地理解本发明，下面举出具体实施例。这些实施例仅用来说明本发明而绝不能理解为是对本发明的范围和对其基本原理的限制。事实上，对本领域的技术人员而言，可从下述实施例和上述说明出发，对本发明进行各种变更是显而易见的。这些变更同样地属于随附的权利要求书的范围。在下述实施例中使用的术语HNMR、CIMS和IR分别表示质子核磁共振、质谱和红外。
实施例1
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮(化合物1)(R1＝Cl、R2＝6-Cl、R3＝CH3、R4＝CH3、R5＝OCH3、X＝O、Y＝O、m＝1、n＝0)
将4-甲基-藜芦醚(76.1克，500mmol)、2，6-二氯苯甲酰氯(120.4克，575mmol)和氯化铁(III)(0.5克)加热搅拌。反应在90℃开始，同时形成氯化氢，主要反应在95℃、于10分钟内完毕。接着，将反应混合液在100℃继续搅拌30分钟，然后冷却至65℃。加入甲醇(350ml)后，化合物1开始结晶。然后在40℃缓慢加入水/甲醇混合液(1∶1v/v；300ml)，将该混合液冷却至室温并搅拌30分钟。减压滤取固体物质，用甲醇/水(3∶1v/v；各100ml)洗涤3次，干燥，得无色结晶148.6克(得率91.4％)，熔点101.5℃。
实施例2
二苯甲酮化合物的衍生化
A)2，6-二氯-4′，5′-二甲氧基-2′-硝基-二苯甲酮(化合物2)(R1＝Cl、R2＝6-Cl、R3＝NO2、R4＝CH3、R5＝OCH3、X＝O、Y＝O、m＝1、n＝0)
将与实施例1类似地制成的一份2，6-二氯-3′，4′-二甲氧基二苯甲酮(6.22克，20mmol)在15分钟内加入已加热至40℃的硝酸(65％；40ml)中。在40℃下搅拌透明溶液10分钟，再在室温下搅拌1小时。然后将反应混合液倾入水中，于是，有缓慢固化的油形成。加热下，将该物质溶于小量的N，N-二甲基甲酰胺，然后加入甲醇，将混合液冷却、过滤，得到呈黄色结晶的化合物2，共5.57克(得率78％)，熔点143℃。
B)2′-氨基-2，6-二氯-4′，5′-二甲氧基二苯甲酮(化合物3)(R1＝Cl、R2＝6-Cl、R3＝NH2、R4＝CH3、R5＝OCH3、X＝O、Y＝O、m＝1、n＝0)
在70℃下，于15分钟内将2，6-二氯-3′，4′-二甲氧基-2′-硝基二苯甲酮(化合物2)(3.56克，10mmol)加至水(50ml)、冰乙酸(1ml)和铁粉(3.30克，60mmol)的混合物中。然后将该反应混合物在95℃继续搅拌3小时。冷却后，加入甲苯50ml，减压滤去固体物。用甲苯洗涤滤饼。合并滤液和洗液，用水洗涤、干燥，然后在快速层析柱中(硅胶，50克)上样。用甲苯、含丙酮1％、2％、5％、10％的甲苯(各250ml)依次洗脱。将被10％丙酮洗脱的部分减压浓缩至最终体积为10ml，由此析出化合物3，得黄色结晶1.61克(得率49％)，熔点181℃。
C)2，6-二氯-4′，5′-二甲氧基-2′-甲酰基氨基-二苯甲酮(化合物4)(R1＝Cl、R2＝6-Cl、R3＝NHCHO、R4＝CH3、R5＝OCH3、X＝O、Y＝(R1＝Cl、R2＝6-Cl、R3＝NHCHO、R4＝CH3、R5＝OCH3、X＝O、Y＝O、m＝1、n＝0)
将2′-氨基-2，6-二氯-4′，5′-二甲氧基二苯甲酮(化合物3；0.82克，2.5mmol)和甲酸(30ml)的混合液回流加热24小时，然后减压蒸馏。将残渣溶于小量甲苯中，加入环己烷，得呈无色结晶的化合物4，共0.64克(得率72％)，熔点152℃。
D)2，6-二氯-5′-羟基-4′-甲氧基-2′-甲基二苯甲酮(化合物5)(R1＝Cl、R2＝6-Cl、R3＝CH3、R4＝CH3、R5＝OH、X＝O、Y＝O、m＝1、n＝0)
将2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮(化合物1；2.5克，7.7mmol)、溴化氢/乙酸(33％，10ml)和冰乙酸(10ml)的混合液在75℃搅拌1.5小时，然后倾入水(100ml)中，用二氯甲烷(各50ml)萃取二次。合并萃取液，干燥、减压浓缩。将所得油状物在快速层析柱(硅胶，30克)顶部上样。用甲苯和甲苯/丙酮(9∶1)各500ml洗脱。合并含Rf＝0.54(硅胶；甲苯/丙酮＝9∶1)的物质的部分，减压蒸去溶剂至达到最终体积20ml。然后用氢氧化钠水溶液(2N)萃取三次(各30ml)。再用盐酸(6M)酸化水层，减压滤取沉淀物，干燥，得呈无色结晶的化合物5，共1.1克(得率45.9％)，熔点152℃。
E)2，6-二氯-4′-甲氧基-2′-甲基-5′-正丙氧基二苯甲酮(化合物6)(R1＝Cl、R2＝6-Cl、R3＝CH3、R4＝CH3、R5＝O-n-C3H7、X＝O、Y＝O、m＝1、n＝0)
将2，6-二氯-5′-羟基-4′-甲氧基-2′-甲基二苯甲酮(化合物5；1.0克，3.2mmol)、正丙基溴(0.5克，4mmol)、碳酸钾(2.8克，20mmol)和乙醇(10ml)的混合物在80℃搅拌6小时，然后过滤，减压蒸馏滤液。将残渣上样至快速层析柱(硅胶，30克)。用甲苯(750ml)洗脱，得呈褐色油状的化合物6，共800毫克(得率70.7％)，油状物缓慢结晶，熔点73-75℃。
F)2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮(化合物7)(R1＝Cl、R2＝6-Cl、R3＝CH3、R4＝O-CH3、R5＝O-CH3、X＝S、Y＝O、m＝1、n＝0)
将2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮(化合物1；3.25克，10.0mmol)、五硫化二磷(2.22克，10.0mmol)和甲苯(50ml)在110℃搅拌5小时，然后用对二噁烷处理，继续在100℃搅拌24小时。从黑色焦油状反应产物中滗去上清液，加入硅胶(15克)，减压蒸去溶剂。将硅胶(100克)装入快速层析柱，在其顶部铺上吸有样品的硅胶。依次用石油醚/丙酮(500ml，98∶2，v/v)和石油醚/丙酮(750ml，95∶5，v/v)洗脱，得呈深绿色油状的化合物7，共40毫克(得率1.2％)，油状物缓慢固化。用环己烷与该油状物一起研磨，共三次，变成固体物，熔点142℃。
实施例3
按与上述实施例1和2基本相同的步骤和使用合适的标准的衍生化技术，制得表1所示的化合物。
Figure C9610101400331
                                        表1
化合物
No.     R1       R2        R2      R3       R4      R5        R6      Y        Mp℃
 8      Cl        6-Cl       H        CH3      CH3     OC2H5     H        O        87
 9      Cl        6-Cl       H        CH3      C2H5   OCH3       H        O        106
10      Cl        6-Cl       H        CH3      CH3     Cl           H        O        168
11      Cl        6-Cl       3-NO2   CH3      CH3     OCH3       H        O        油
12      Br        H          H        CH3      CH3     OCH3       H        O        69-71
13      Cl        6-Cl       H        CH3      CH3     OC(O)C2H5 H        O        142-145
14      Cl        6-Cl       H        CH3      CH3     H           H        O         89
15      I         H          H        CH3      CH3     OCH3       H        O         66-68
16      Cl        6-CH3     H        CH3      CH3     OCH3       H        O         56
17      Cl        6-CH3     H        F         CH3     OCH3       H        O         95
18        (CH＝CH)2         6-Cl     CH3      CH3     OCH3       H        O
19      I         3-I        5-I      CH3      CH3     OCH3        H        O        油
20      Br        5-Br       H        CH3      CH3     OCH3        H        O        油
21      Cl        4-NO2     H        CH3      CH3     OCH3        H        O        126-128
                                     表1(续)
化合物
No.       R1     R2    R2     R3     R4     R5      R6     Y      Mp℃
22        Cl      6-Cl    H       CH3    CH3    SCH3    H       S      105
23        Cl      6-Cl    H       CH3    CH3    OCH3    2-OCH3 O      92
24        Cl      6-Cl    H       CH3            CH2O    H        O      142
25        Cl      6-Cl    H       CH3    CH3    I        H        S
26        Br      5-OCH3 H       CH3    CH3    OCH3    H       O      油
27        Cl      5-Br    H       CH3    CH3    OCH3    H       O      94-96
28        Cl      6-Cl    H       CH3    CH3    OC(O)CH- H       O      132-135
                                                  (CH3)2
29        Cl      5-Cl    6-OCH3 CH3    CH3    OCH3    H      O       油
30        Cl      6-Cl    H       CF3    CH3    Cl       H       O
31        Cl      6-Cl    H       CH3    CH3    OCHF2   H       O      126-128
32        CF3    5-CF3 H       CH3    CH3    OCH3    H       O      98-101
33        Cl      6-Cl    H       CH3    CH3    H        3-OCH3 O      100-125
                                    表1(续)
化合物
No.       R1     R2     R2     R3        R4     R5        R6     Y      Mp℃
34        Cl      6-Cl    H       CH3       CH3    OC(O)C-     H       O      167
                                                     (CH3)3
35        Cl      6-Cl    H       CH3       H       OH           H       O      201-203
36        Cl      6-Cl    H       SCH3      CH3    OCH3       H       O      185
37        Cl      6-Cl    H       S(O2)CH3 CH3    OCH3       H       O      163
38        Cl      6-Cl    H       CH3       CH3    CH3        3-CH3  O      78
39        Cl      6-Cl    H       S(O)CH3   CH3    OCH3       H       O      178
40        Cl      6-Cl    H       CH3       CH3    OCH2CH＝CH H       O      油
                                                      2
41        Cl      3-Cl    5-Cl    CH3       CH3    OCH3       H       O      99-101
42        Cl      6-Cl    H       CH3      (CH2)2 O           H       O      油
43        Cl      6-Cl    H       CH3       CHF2   OCHF2      H       O      65-68
44        CF3    6-CF3 H       CH3       CH3    OCH3       H       O      105-107
45        Cl      6-Cl    H       CH＝CH2   CH3    OCH3       H       O
                                    表1(续)
化合物
No.      R1     R2     R2     R3       R4     R5      R6     Y      Mp℃
46       I       6-F     H       CH3      CH3    OCH3     H       O      油
47       Cl      3-Cl    H       CH3      CH3    OC2H5   H       O      97
48       Cl      6-Cl    H       CH3      C2H5  OC2H5   H       O      77
49       Cl      6-Cl    H       CH＝CH-CN CH3    OCH3      H       O
50       Cl      6-Cl    H       CH3      CH3    OCH3      3-Br    O      86
51       Cl      4-Cl    5-Cl    CH3      CH3    OCH3      H       O      160
52       Cl      6-Cl    H       CH3      CH3    C4H9- t H       O      124
53       Cl      6-Cl    H       CH3      CH3    OC4H9- n H       O      51
54       Cl      6-Cl    H       CH3      CH3    OC4H9- i H       O      油
55       Cl      6-Cl    H       CH3      CH3    H            H       S
56       Cl      6-Cl    H       CH3      CH3    OCH2C6H5 H       O      119-121
57       Cl      6-Cl    H       CH3      CH3    OC5H11- n H       O      46-48
58       Cl      6-Cl    H       CH3      CH3    OC3H7- i  H       O      油
59       Cl      6-Cl    H       CH3      CH3    OCH3        2-OH    O      161
                                     表1(续)
化合物
No.       R1     R2     R2     R3     R4     R5        R6        Y      Mp℃
60        Cl      6-Cl    H       CH3    CH3    OCH2C(O)-  H          O      105-108
                                                   OC2H5
61        Cl      6-Cl    H       CH3    CH3    H           2-OCH3    O      135
62        Cl      6-Cl    H       CH3    CH3    OCH3       2-OC2H5 O      72
63        Cl      6-Cl    H       CH3    CH3    Cl          H          S
64        Cl      4-Cl    6-Cl    CH3    CH3    OCH3       H          O      108-109
65        Cl      6-Cl    H       CH3    CH3    Br          H          S
66        F       6-F     H       CH3    CH3    OCH3       H          O      75-77
67        Cl      H       H       CH3    CH3    OCH3       H          O      油
68        Cl      4-Cl    H       CH3    CH3    OCH3       H          O      油
69        Cl      6-Cl    H       CH3    CH3    CH3        H          O      135-138
70        Cl      6-Cl    H       CF3    CH3    Br          H          O
71        Cl      5-Cl    H       CH3    CH3    OCH3       H          O      100-102
72        Cl      6-Cl    H       C2H5  CH3    OCH3       H          O      油
                                        表1(续)
化合物
No.       R1      R2      R2      R3          R4      R5       R6      Y      Mp℃
73        Cl       3-Cl     H        CH3         CH3     OCH3      H        O      油
74        Cl       6-Cl     H        CN           CH3     OCH3      H        O      120
75        F        6-CF3   H        CH3         CH3     OCH3      H        O      油
76        Cl       6-Cl     H        CH3         CH3     OCH2CN    H        O      127
77        Cl       6-F      H        CH3         CH3     OCH3      H        O      72-73
78        Cl       6-Cl     H        I            CH3     OCH3      H        O      101
79        Cl       6-Cl     H        C3H7- n   CH3     OCH3      H        O     72
80        Cl       6-Cl     H        CH3         CH3     OC(O)CH3  H        O      156-159
81        Cl       6-Cl     H        Br           CH3     OCH3      H        O      124
82        Cl       6-Cl     H        CH3         CH3     OCH2C≡CH H        O      87
83        Cl       6-Cl     H        H            CH3     H           3-OCH3  O     127
84        Cl       6-Cl     H        CH3         H        H           3，6-di-  O     122
                                                                        CH3
                                         表1(续)
化合物
No.       R1      R2      R2     R3       R4       R5        R6       Y       Mp℃
85        Cl       6-Cl     H        CH3     CH3       H          3，6-di-  O       111
                                                                     CH3
86        Cl       6-Cl     H        CF3     C(O)-      H           H         O       186
                                              2，6-
                                              Cl2C6H3
87        CH3     6-CH3   H        H        CH3       H           3-OCH3   O       84
88        Cl       6-Cl     H        H        CH3        H           3-Br      O       129
89        Cl       6-Cl     H        H        CH3        Br          3-OCH3   O       140
90        Cl       6-Cl     H        OCH3    CH3        OCH3       H         O       124
91        Cl       6-Cl     H        CH3     CH3        OC(O)H      H         O       156
92        OCH3   6-OCH3  H        CH3     CH3        OCH3       H         O       113
93        Cl       6-Cl     H        COOH     CH3        OCH3       H         O       174
94        Cl       6-Cl     H        CH3     CH3        S(O)2CH3  H         SO2    233
95        Cl       6-Cl     H        CH3     CH3        SOCH3      H         SO      227
96        Cl       6-Cl     H        CH3     CH3        On-C7H15 H         O       油
Figure C9610101400411
                                      表1(续)
化合物
No.       R1     R2     R2     R3     R4     R5          R6     Y      Mp℃
97        Cl      6-Cl    H       CH3    CH3    On-C8H17   H       O      油
98        Cl      6-Cl    H       CH3    CH3    On-C10H21  H       O      油
99        CH3    4-CH3 6-CH3  CH3    CH3    OCH3         H       O      74
100       Cl      6-Cl    H       CH3    CH3    OCH2-c-      H       O      油
                                                   C3H5
101       Cl      6-Cl    H       CH3    CH3    OCH2-c-      H       O      108
                                                   C6H11
102       Cl      6-Cl    H       CH3    CH3    O(CH2)2-    H       O      油
                                                   CH(CH3)2
103       Cl      6-Cl    H       CH3    CH3    OCH2CH＝C     H      O      油
                                                   -(CH3)2
104       CH3    6-CH3  H       CH3    CH3    OCH3         H       O      90-92
105       Cl      6-Cl    H       CH3    CH3    Oc-C5H9     H       O      油
106       Cl      6-Cl    H       CH3    CH3    Oc-C6H11    H       O      油
Figure C9610101400421
                                           表1(续)
化合物
No.        R1      R2       R2       R3      R4      R5            R6      Y      Mp℃
107        Cl       6-Cl      H         H        CH3 [3]-(CH＝CH-)2-[2] H               155-
                                                                                           157
108        Cl       6-Cl      H         CH3     CH3     ONa             H        O       玻璃
109        Cl       6-Cl      H         CH3     CH3     OSi(CH3)       H        O       油
                                                           3
110        Br       6-Br      H         CH3     CH3     OCH3           H        O       102
111        Cl       6-Cl      H         CH3     CH3     OK              H        O       98
112        Cl       6-Cl      H         OCH3    CH3     Br              2-OCH3  O       183
113        CN       H         H         CH3     CH3     OCH3           H        O       76
114        Cl       6-Cl      H         CH3        -CH2O-               2-OCH3          98
115        Cl       6-Cl      H         NH-CH3  CH3     OCH3           H                163
116        Cl       6-Cl      H         OH       CH3     OCH3           H         O       80
117        Cl       6-Cl      H         CH3     CH3     OCH2-          H         O       油
                                                         Si(CH3)3
118        Cl       H         H         CH3    CH3      OCH3           H         O       62-64
                                      表1(续)
化合物
No.        R1     R2      R2     R3     R4        R5      R6          Y      Mp℃
119        Cl      3-Cl     H       CH3   CH3     OCH3       2-OCH3       O      油
120        Cl      4-Cl     6-Cl    CH3   CH3     OCH3       H             O      126
121        F       6-F      H       CH3   CH3     OCH3       H             O      84
122        Cl      5-Cl     H       CH3   CH3     OCH3       H             O      油
123        Cl      6-Cl     H       OCH3  CH3     CH3        6OCH3        O      115
124        I       H        H       CH3   CH3     OCH3       2-OCH3       O      油
125        Br      H        H       CH3   CH3     OCH3       H              O      34
126        Cl      6-Cl     H       CH3   CH3     O n-C6H13 H             O      油
127        Cl      6-Cl     H       CH3   CH3     OCH3        2O n-C3H7 O      46
128        Cl      6-Cl     H       CH3   CH3     OCH3        2O n-C7H15 O      油
129        Cl      6-Cl     H       CH3   CH3     OCH3        2O n-         O      油
                                                                  C10H21
130        Cl      6-Cl     H       CH3   CH3     OCH3        2-OC(O)-       O      164
                                                                  CH3
                                         表1(续)
化合物
No.       R1      R2      R2      R3      R4      R5      R6        Y       Mp℃
131       Cl       6-Cl     H        CH3     CH3     OCH3    2O n-       O       油
                                                                 C5H11
132       Cl       6-Cl     H        CH3     CH3     OCH3    2O(CH2)2  O       101
                                                                 -CH-
                                                                 (CH3)2
133       Cl       6-Cl     H        CH3     CH3     OCH3    2OCH2-      O       73
                                                                 CH＝CH2
134       Cl       6-Cl     H        CH3     CH3     OCH3    2OCH2C≡CH  O       123
135       Cl       6-Cl     H        CH3     CH3     OCH3    2Oc-C5H9   O       89
136       Cl       6-Cl     H        CH3     CH3     OCH3    6OCH2-      O       80
                                                                 C6H5
137       Cl       6-Cl     H        CH3     CH3     OCH3    2On-         O       油
                                                                 C12H25
138       Cl       6-Cl     H        CH3     CH3     OCH3    2OCH2-      O       88
                                                                 c-C6H11
Figure C9610101400451
                                          表1(续)
化合物
No.       R1      R2      R2       R3      R4       R5           R6     Y        Mp℃
139       Cl       6-Cl     H         CH3      CH3     OCH3         2O n-    O        油
                                                                        C6H13
140       Cl       6-Cl     H         CH3      CH3     O n-C12H25 H          O        油
141       Cl       6-Cl     H         CH3      CH3     OCH2C(O)N    H          O        97
                                                          -(C2H5)2
142       Cl       6-Cl     H         CH3      CH3     OCH2C(O)N    H          O        136
                                                          -H2
143       Cl       6-Cl     H         CH3      CH3     OCH3         2O(CH2)2 O        84
                                                                        -OCH3
144       Cl       6-Cl     H         CH3      CH3     OCH-          H           O        油
                                                         (C2H5)2
145       Cl       6-Cl     H         CH3      CH3     O(CH2)2-    H          O        87
                                                          OH
146       Cl       6-Cl     H         CH3      CH3     O(CH2)3-    H          O        86
                                                          OH
                                           表1(续)
化合物
No.       R1      R2       R2      R3      R4        R5          R6       Y      Mp℃
147       Cl       6-Cl      H        CH3     CH3       OCH2-p-      H         O      油
                                                           C6H4-CH3
148       Cl       6-Cl      H        CH3     CH3       OCH2-p-      H         O      119
                                                           C6H4-
                                                           C(CH3)3
149       Cl       6-Cl      H        CH3     CH3       OCH3        2OCH2C(O) O      油
                                                                        -
                                                                        酰吗啉
150       Cl       6-Cl      H        CH3     CH3      O(CH2)2OC     H         O      油
                                                          H3
151       Cl       6-Cl      H        CH3     CH3      OCH2-          H         O      163
                                                          C(O)-
                                                          酰吗啉
Figure C9610101400471
                                          表1(续)
化合物
No.        R1     R2      R2      R3      R4      R5           R6         Y       Mp℃
152        Cl      6-Cl     H        CH3      CH3     OCH2-p-      H           O       油
                                                         C6H4-OCH3
153        Cl      6-Cl     H        CH3      CH3     O(CH2)3OC   H           O       油
                                                        6H5
154        Cl      6-Cl     H        CH3      CH3     OCH3        2O(CH2)3   O       225
                                                                      -
                                                                     吗啉基
                                                                     ×HCl
155        Cl      6-Cl     H        CH3      CH3     OCH3        2O(CH2)2   O       103
                                                                     -N(CH3)2×
                                                                     HCl
156        Cl      6-Cl     H        CH3      CH3     OCH3       2O(CH2)2    O       144
                                                                     -
                                                                     N(C2H5)2×
                                                                     HCl
157        Cl      6-Cl     H        CH3      CH3     OC2H5     2-OCH3       O       68
Figure C9610101400481
                                          表1(续)
化合物
No.       R1      R2      R2      R3       R4      R5      R6         Y      Mp℃
158       Cl       6-Cl     H        CH3     CH3       OCH3    2O(CH2)3  O      87
                                                                   Cl
159       Cl       6-Cl     H        CH3     CH3       OCH3    2O(CH2)3  O      70
                                                                   -
                                                                   哌啶基
                                                                   ×HCl
160       Cl       6-Cl     H        CH3     n-C7H15 OCH3      H           O      51
161       Cl       6-Cl     H        CH3     n-C3H7  OCH3      H           O      80
162       Cl       6-Cl     H        CH3     n-C4H9  OCH3      H           O      89
163       Cl       6-Cl     H        CH3     CH3       CH(CH3)2 H           O      96
164       CH3     3-CH3  H        CH3     CH3       OCH3       6-OCH3     O      82
165       CH3     5-CH3  H        CH3     CH3       OCH3       6-OCH3     O      油
166       Cl       6-Cl     H        Cl       CH3       OCH3       H           O      114
167       Cl       6-Cl     H        CH3     CH3       O(CH2)3-  H           O      油
                                                          CO2C2H5
Figure C9610101400491
                                         表1(续)
化合物
No.       R1      R2      R2      R3      R4      R5               R6         Y        Mp℃
168       Cl       6-Cl     H        CH3     CH3     OCH2C6H4-      H            O       115-117
                                                        CF3-p
169       Cl       6-Cl     H        CH3     CH3     OCH2SiC2H5(    H            O       85
                                                        CH3)2
170       Cl       6-Cl     H        CH3     CH3     OC(CH3)3        H            O       102
171       Cl       6-Cl     H        CH3     CH3     OCH2CH2OCH2    H            O       油
                                                        CH2OCH
172       Cl       6-Cl     H        CH3     CH3     O(CH2)4Br         H            O       油
173       Cl       6-Cl     H        CH3     CH3     OCH3          6-O(CH2)3N-   O       油
                                                                      (C2H5)2
174       Cl       6-Cl     H        CH3     CH3     OCH3          6-OCH-           O       108
                                                                      (CH3)2
175       Cl       6-Cl     H        CH3    CH3     OCH3          6-OCH2CH2-      O       油
                                                                      OCH2CH2OCH3
Figure C9610101400501
                                        表1(续)
化合物
No.      R1     R2      R2      R3       R4    R5            R6        Y      Mp℃
176      Cl      6-Cl     H        CH3       CH3   OCOC6H3Cl2 6-OCH3     O      186-189
                                                      -2，6
177      Cl      6-Cl     H        H          CH3   OCH3          6-OCH3     O      97
178      Cl      6-Cl     H        CH3       CH3   CH3           6-OCH3     O      106
179      Cl      6-Cl     H        OCH3      CH3   OCH3          6-OCH3     O      121-123
180      Cl      6-Cl     H        CH1       CH3   NHCOCH3       H            O      155
181      Cl      6-Cl     H        CH3       CH3   OH             6-OH         O      182
182      CF3    H        H        CH3       CH3   OCH3         6-OCH3      O      油
183      CF3    H        H        CH3       CH3   OCH3         H             O      油
184      Cl      6-Cl     H        CH3       CH3   OC4H9-n     6-OC4H9-n  O      油
185      Cl      6-Cl     H        CH(CH3)2 CH3   CH3          H             O      110
186      Cl      6-Cl     H        CH3        H      NO2          H             O      170
195        O-CF2O        H        CH3       CH3   OCH3         H              O
实施例4
2′-正丁氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮(化合物187)
(R1＝Cl、R2＝6-Cl、R3＝CH3、R4＝CH3、R5＝OCH3、R6＝2-O-(CH2)3-CH3、X＝O、Y＝O、m＝1、n＝0)
a)2，6-二氯-3′，4′-二甲氧基-2′-羟基-6′-甲基二苯甲酮(化合物59)
在0℃下，边搅拌边缓慢地将氯化铝(14.67克，0.1mol)、2，6-二氯苯甲酰氯(20.95克，0.1mol)和3，4，5-三甲氧基甲苯(18.22克，0.1mol)在二氯甲烷(50ml)中的溶液依次连贯地加入二氯甲烷中，在冰溶中搅拌1小时后，在室温下再搅拌16小时，然后倾入冰中。分出有机层，用稀盐酸和水洗涤，干燥，加入硅胶(100克)，减压浓缩。将硅胶(400克)装入快速层析柱中，在其顶部铺上吸有样品的硅胶。用石油醚/乙酸乙酯(90/10，1升；80/20，1升；50/50，1升)洗脱，得2，6-二氯-3′，4′-二甲氧基-2′-羟基-6′-甲基二苯甲酮10.35克，得率30％，熔点161℃。
b)2，6-二氯-3′，4′-二甲氧基-2′-羟基-6′-甲基二苯甲酮，钾盐(化合物188)
(R1＝Cl、R2＝6-Cl、R3＝CH3、R4＝CH3、R5＝OCH3、R6＝2-OK、X＝O、Y＝O、m＝1、n＝0)
将2，6-二氯-3′，4′-二甲氧基-2′-羟基-6′-甲基二苯甲酮(10.24克，30mmol)的溶液溶于氢氧化钾(1.98克，30mmol)在乙醇中的溶液(85％乙醇溶液，100ml)，并于70℃下搅拌15分钟。然后减压蒸去溶剂。将残渣溶于热乙醇(50ml)中，加入甲苯，减压蒸去溶剂，得化合物188，共11.7克。
c)2′-正丁氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮(化合物187)
将2，6-二氯-3′，4′-二甲氧基-2′-羟基-6′-甲基二苯甲酮，钾盐(1.13克，3mmol)、1-溴丁烷(0.69克，5mmol)和二甲基甲酰胺(5ml)的混合液在100℃搅拌8小时，减压浓缩。用甲苯/水混合液振荡溶解残渣，分出有机层，用水洗涤，干燥。加入硅胶(5克)后蒸去溶剂。将硅胶(25克)装入快速层析柱中，在其顶部铺上吸有样品的硅胶。用石油醚/乙酸乙酯(95/5，500ml)洗脱，得标题化合物0.82克；得率69％，为无色结晶，熔点70℃。
实施例5
按与上述实施例1、2和4基本相同的步骤和根据需要，使用标准的衍生化方法制得表2所示的化合物。
                                                表2
化合物
No.      R1     R2            m       R3     Y-R4   R5                  R6     n     mp℃
189      CH3    3，5，6-CH3   3       CH3    OCH3   OCH3                H       0     103
190      CH3    CH3           4       CH3    OCH3   OCH3                H       0     142-144.5
191      CH3    3，5，6-CH3   3       CH3    OCH3   OCH3                6-OCH3 1     113
192      CH3    3，5，6-CH3   3       CH3    OCH3   OCH2CH2CH(CH3)2 H        0     73
193      CH3    3，5，6-CH3   3       CH3    OCH3   OCH2CH2CH3       H        0     85
194      CH3    3，5，6-CH3   3       CH3    OCH3   OCH3                6-OH     1     137
实施例6
2，6-二氯-3′，4′-二甲氧基二苯甲酮肟(化合物195)(R1＝Cl、R2＝6-Cl、R3＝H、Y＝O、R4＝CH3、R5＝H、R6＝4-OCH3、R＝H)
在冰浴温度下，将无水氯化铝(2.93克，22mmol)在二氯甲烷中的分散液在搅拌下依次用2，6-二氯苄腈氧化物(3.76克，20mmol)在二氯甲烷中的溶液处理，然后滴加藜芦醚(3.32克，24mmol)在二氯甲烷中的溶液，搅拌0.5小时，让其温热至室温，再搅拌4-5小时后，倾入冰和盐酸的混合物中，从所得的相混合物中分出有机相，用2M HCl洗涤，再用硅胶处理，减压蒸干。将残渣置于硅胶柱顶部，用石油醚和乙酸乙酯的混合液(分别为5％、10％和20％石油醚)洗脱，得呈白色固体状的标题化合物1.25克(得率19％)，熔点153℃。
实施例7
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮-O-正丙肟(化合物196)(R1＝Cl、R2＝6-Cl、R3＝CH3、Y＝O、R4＝CH3、R5＝OCH3、R6＝H、R＝n-C3H7)
将2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮肟(1.5克，4.4mmol)搅拌加入无水四氢呋喃中，然后用氢化钠在矿物油中的60％分散体(0.2克，4.8mmol NaH)处理。待氢气停止产生后，用正丙基碘(0.82克，5.2mmol)处理反应混合液，室温下放置12小时，用水稀释。再用乙酸乙酯萃取所得相混合物。合并有机相，减压浓缩。将所得残渣用硅胶和石油醚/乙酸乙酯(8/2)层析，得呈黄色油状的标题化合物0.4克(得率23.8％)，用NMR鉴定，E/Z异构体比为67∶23。
实施例8
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮-O-乙酰基肟(化合物197)
(R1＝Cl、R2＝6-Cl、R3＝CH3、Y＝O、R4＝CH3、R5＝OCH3、R6＝H、R＝COCH3)
将2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮肟(2.3克，6.8mmol)搅拌加入无水四氢呋喃中，然后用氢化钠在矿物油中的60％分散体(0.3克，7.5mmol NaH)处理。待氢气停止产生后，用乙酰氯(0.55克，7.5mmol)在室温处理反应混合液，使其放热至30℃，在环境温度下搅拌2小时，减压浓缩，用水处理，过滤。将滤饼用水洗涤、干燥，用甲醇进行重结晶，得呈白色晶状的标题化合物1.0克(得率38.5％)，熔点158-149℃，用NMR鉴定，E异构体为100％。
实施例9
按与上述实施例6-8基本相同的步骤得表3所示的化合物。
                             表3
化合物No.       R                 R3         R6        mp.℃
198             H                 F           F          油
199             H                 H           H          153
200             H                 CH3        H          60-60
201             H                 CH3        6-OCH3    219-220
202             CH3              CH3        H          112-115
203             CH(CH3)2        CH3        H          117
204             CH2CH2CH2CH2  CH3        H          油
实施例10
2，6-二氯-2′，3′，4′-三甲氧基-6′-甲基二苯甲酮
将3，4，5-三甲氧基甲苯(9.11克，50mmol)、辛烷(25ml)和氯化铁(III)(50毫克)在105℃搅拌，通氮下在15分钟内滴加2，6-二氯苯甲酰氯(12.04克，57.5mmol)。将该混合物保持在105℃并继续搅拌15分钟。冷却至50℃后，加入乙酸乙酯(50ml)，用2N盐酸振摇二次，用水振摇一次，干燥。(70℃下)蒸去乙酸乙酯，将液体在搅拌下进行冷却。在50℃加入石油醚(50ml)。吸滤形成的白色结晶，用石油醚洗涤、干燥。得12.55克(得率70.7％)，熔点92℃。
实施例11
2，6-二氯-2′，3′-二羟基-4′-甲氧基-6′-甲基二苯甲酮
将2，6-二氯-2′，3′，4′-三甲氧基-6′-甲基二苯甲酮(1.78克，5mmol)、氢溴酸(7.5ml，30％乙酸溶液)和乙酸(7.5ml)的混合物在75℃搅拌2小时。加入水，用二氯甲烷萃取混合物。萃取物用水洗涤，用2N氢氧化钠振摇。然后用盐酸酸化碱性溶液，分出的化合物溶于二氯甲烷中，溶液用水洗涤。蒸去溶剂后进行层析纯化(快速层析柱，装有36克硅胶)，用500ml石油醚/乙酸乙酯(4∶1，v/v)和250ml石油醚/乙酸乙酯(1∶1，v/v)洗脱。浓缩含化合物的部分；化合物结晶。用石油醚洗涤黄色结晶，吸滤，得0.64克(得率39％)，熔点182℃。
实施例12
2′，3′-二正丁氧基-2，6-二氯-4′-甲氧基-6′-甲基二苯甲酮
向2，6-二氯-2′，3′-二羟基-4′-甲氧基-6′-甲基二苯甲酮(1.64克，5mmol)在四氢呋喃中的溶液中边搅拌边加入氢化钠(0.4克，60％，10mmol)。蒸去溶剂，将残渣溶于30ml二甲基甲酰胺。加入1-碘正丁烷(4.6克，25mmol)，将混合物在100℃搅拌8小时，然后蒸去溶剂。用甲苯/2N盐酸振摇残渣，分出有机层，水洗，蒸去溶剂。残渣用层析法纯化(装有35克硅胶的快速柱，用500ml含2％乙酸乙酯的石油醚洗脱)，得黄色油状物(0.7克，得率32％)。
实施例13
7-(2，6-二氯苯甲酰基)-10-甲氧基-8-甲基-2，3，4，5-四氢-1，6-苯并二氧杂环辛二烯
(R5+R6＝-O-(CH2)4-O-)
将2，6-二氯-2′，3′-二羟基-4′-甲氧基-6′-甲基二苯甲酮(3.27克，10mmol)、碳酸钾(4克)、氧化铜(II)(50毫克)、1，4-二溴丁烷(2.38克，11mmol)和二甲基甲酰胺(25ml)的混合物在室温搅拌15小时。加入水，用乙酸乙酯萃取二次。乙酸乙酯相用水洗涤，蒸去溶剂。用层析法(硅胶快速层析柱，石油醚/乙酸乙酯(8∶2，v/v)洗脱)纯化残渣。合并富集目的化合物的部分，用甲醇结晶，得白色结晶0.56克(得率14.7％)，熔点103～104℃。
实施例14
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-苯基乙酰氧基-二苯甲酮
将2，6-二氯-3′，4′-二甲氧基-2′-羟基-6′-甲基二苯甲酮(3.41克，10mmol)加入氢氧化钾(0.66克)在甲醇中的溶液(85％)(30ml)中。蒸去甲醇，将残渣溶于二甲基甲酰胺(30ml)中，加入苯基乙酰氯(1.70克，11mmol)，将混合液搅拌15小时。再加入水，用乙酸乙酯萃取混合液三次。蒸去溶剂，加入甲醇，得白色结晶1.95克(得率42.5％)，熔点106℃。
实施例15
2，6-二氯-5′-二氟甲氧基-4′-甲氧基-2′-甲基二苯甲酮
向2，6-二氯-5′-羟基-4′-甲氧基-2′-甲基二苯甲酮(1.0克，3.2mmol)在二甲氧基乙烷(7ml)中的溶液中加入氢氧化钠(0.6克，15mmol)在水(1ml)中的溶液。边搅拌边加热混合物至60℃，然后导入二氟氯甲烷气流20分钟。继续搅拌1.5小时后，蒸去溶剂。用三氯甲烷和水的混合物萃取混合液。分出有机相，干燥，蒸去溶剂。用硅胶(30克)快速层析柱纯化(依次用石油醚/乙酸乙酯9∶1、8∶2和7∶3(v/v)洗脱)。所得化合物成为白色结晶0.6克(得率51.8％)，熔点126～128℃。
实施例16
2，6-二氯-5′-丙酰氧基-4′-甲氧基-2′-甲基二苯甲酮
将2，6-二氯-5′-羟基-4′-甲氧基-2′-甲基二苯甲酮和丙酸酐(5ml)的混合物在100℃搅拌5小时。加入甲苯/水。干燥有机相，蒸出溶剂。用层析法纯化残渣(30克硅胶快速层析柱，甲苯洗脱)。除去甲苯。用环己烷处理残渣，得白色结晶0.5克(得率42.6％)，熔点142-145℃。
实施例17
2，6-二氯-5′-叔丁氧基-4′-甲氧基-2′-甲基二苯甲酮
将2，6-二氯-5′-羟基-4′-甲氧基-2′-甲基二苯甲酮(3.0克，9.6mmol)在50ml二氯甲烷中的溶液冷却至-70℃，加入三氟甲磺酸(0.3ml)，再在4小时内导入2-甲基丙烯(5.5克，100mmol)气。加入三乙胺(1.2ml)，温度升至20℃。用稀氢氧化钠振摇溶液二次，蒸去溶剂。层析(30克硅胶快速层析柱，甲苯/丙酮20∶1(v/v)洗脱)纯化残渣。用石油醚处理残渣，得白色结晶0.7克(得率20％)，熔点102℃。
实施例18
2，6-二氯-4′-甲氧基-2′-甲基-5′-苯氧基二苯甲酮
将2-甲氧基-4-甲基二苯醚(2.1克，10mmol)、2，6-二氯苯甲酰氯(2.5克，12mmol)和氯化铁(III)的混合物加热至100℃并搅拌4小时。冷却后，用甲苯/水振摇混合物。干燥有机层，蒸去溶剂。层析(30克硅胶快速层析柱，甲苯/石油醚1∶9至1∶1(v/v)洗脱)纯化残渣。蒸干后，用二异丙醚处理残渣，得白色结晶1.5克(得率39％)，熔点113.5℃。
实施例19
2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮
将2，6-二氯苯甲酰氯(0.24克，25mmol)、3-甲基茴香醚(2.44克，20mmol)和氯化铁(III)(20毫克)的混合物加热到100℃并搅拌45分钟。冷却后，加入甲苯，用水振摇混合物，干燥有机相，蒸去溶剂。层析反应产物(70克硅胶快速层析柱，石油醚/甲苯从75∶25变至40∶60(v/v)洗脱)。将主要流出部分蒸干后的残渣用石油醚来处理，得白色结晶1.33克(得率22.5％)，熔点89℃。
实施例20
5′-溴-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮
将溴(0.25ml)在三氯甲烷(3ml)中的溶液滴加至搅拌中的2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮(1.5克，5mmol)在三氯甲烷(5ml)中的溶液，再在20℃搅拌15分钟。依次用水、碳酸氢钠溶液和水振摇混合物。干燥有机相，蒸出溶剂。层析(装有30克硅胶的快速层析柱，石油醚/乙酸乙酯洗脱，从20∶1变至9∶1、8∶2、7∶3(v/v))纯化残渣。蒸出溶剂后，用石油醚/甲苯处理残渣，得白色结晶0.45克(得率24％)，熔点150℃。
实施例21
2，6-二氯-5′-硝基-4′-甲氧基-2′-甲基二苯甲酮
将2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮(0.75克，2.5mmol)加入硝酸(10ml，65％)中。将混合液在80℃搅拌1小时。加入水后，反应产物结晶，层析纯化(30克硅胶快速层析柱，甲苯洗脱)，得白色结晶0.35克(得率41％)，熔点156～160℃。
实施例22
2，6-二氯-4′-羟基-5′-硝基-2′-甲基二苯甲酮
将氯化铝(1.5克，11mmol)加入2，6-二氯-5′-硝基-4′-甲氧基-2′-甲基二苯甲酮(1.8克，5.3mmol)在二氯甲烷(6ml)中的溶液中。将混合物在20℃搅拌30分钟，再在45℃搅拌1小时，加入5ml浓盐酸/冰。用20ml二氯甲烷振摇后，依次用2N盐酸和水处理有机相。干燥后，蒸去溶剂，层析(30克硅胶快速层析柱，甲苯洗脱)纯化残渣。用二异丙醚处理得自主要流出部分的残渣后，得黄色结晶1.2克(得率73％)，熔点170℃。
可用与上述实施例类似的方法制得表4至表10所示的化合物。
Figure C9610101400611
                          表4
化合物
No.  R5                                             mp.[℃]
1    O-C6H5                                        113.5
2    Br                                               159
3    NO2                                             156-60
4    O-CH2-CONH-(4-OCH3-C6H4)                    154
5    O-CH2-CONH-C6H5                              133
6    O-CH2-CONH-CH2-C6H5                         150
7    O-CH2-(2-吡啶基)                                114
8    O-CH2-(3-吡啶基)                                119
9    O-CH2-(4-吡啶基)                                142
        134
11   O-(CH2)4-O-C6H5                              86-9
Figure C9610101400613
    124
表4(续)
                     表5
Figure C9610101400631
化合物
No.                 (R2)m              mp.[℃]
1                   3-CH3               82
2                   5-CH3               油
3                   5-CH3               89
4                   4，6-(CH3)2        142
                    表6
化合物
No.         R                                mp.[℃]
1           CH2-CH(CH3)2                105
2           CH2-CH(C2H5)2              65
3           CH2-(2-CH3-C6H4)           73
4           CH2-(3-CH3-C6H4)           88
5           CH2-(4-CH3-C6H4)           92
6           CH2-(4-Cl-C6H4)             121
7           CH2-(4-NO2-C6H4)           178
8           CH2-(4-F3CO-C6H4)          120
9           CH2-(4-CN-C6H4)             189
Figure C9610101400642
  119
11          CH2-(3-CH3O-C6H4)          油
12          CH2-(4-H2NCO-C6H4)         106
13          CH2-(4-CH3O-C6H4)          77
14          H                               161
15              CH2-CO-C6H5                84
No.             R                             mp.[℃]
16              CH2-CH＝CH-C6H5             油
17              CH2-(4-CO2CH3-C6H4       106
18              CH2-CH2-CH2-C6H5         79
19              CH2-(2，5-(CH3)2-C6H3)   86
20              CH2-(2，4-(CH3)2-C6H3)   125
21              CO-CH2-C6H5                 106
22              CH2-(2-萘基)                   84
23              CH2-CH2-CH2-O-C6H5        79
24              CH2-CH2-C6H5               110
25              CH2-CH2-O-C6H5             油
26              CH2-(2-Cl-C6H4)             131
27              CH2-(3-Cl-C6H4)             124
28              CH2-(2-F-C6H4)              88
29              CH2-(4-F-C6H4)              102
30              CH2-(2-CN-C6H4)             127
31              CH2-(3-F-C6H4)              88
32              CH2-(3-吡啶基)                 84
33              CH2-(2-NO2-C6H4)           140
34              CH(CH3)-C6H5                 92
35              CH2-(4-CF3-C6H4)           125
                     表7
化合物
No               k                      mp.[℃]
1                1                      119
2                2                      123-5
3                3                      133
4                4                      103
                       表8
化合物
No.         R            R′                    mp.[℃]
1           H            n-C7H15               油
2           CH3         n-C7H15               油
3           H            CH2-CH2-CH(CH3)2    63
4           H            CH2-S-C6H5
5           CH3          CH2-S-t-C4H9
                             表9
Figure C9610101400681
化合物
No.            R                       R′                    mp.[℃]
1              O-CH3                 n-C5H11              油
2              O-CH2-CH2-S-C6H5  CH3
3              O-CH2-CO-C(CH3)3   CH3
4              H                      CH2-O-CH2-C6H5
5              H                      CH2-S-CH3
6              H                      CH2-SO2-C6H5
7              H                      CH2-S-C6H5
8              CH3                   CH2-S-t-C4H9
9              OH                     H                       182
10             OH                     CH3
11             O-CH2-O-C6H5       CH3
                           表10
Figure C9610101400691
化合物
No.           R                          R1                     mp.[℃]
1             O-CH3                     n-C5H11
2             O-CH2-CH2-S-C6H5      CH3
3             O-CH2-CO-C(CH3)3       CH3
4             H                          CH2-O-CH2-C6H5
5             H                          CH2-S-CH3
6             H                          CH2-SO2-C6H5
7             H                          CH2-S-C6H5
8             O-CH3                     CH2-S-C6H5
9             O-CH2-O-CH2-C6H5      CH3
10            O-CH2-O-C6H5           CH3
11            H                          OH
                         表10
          
Figure C9610101400701
化合物
No.            R                       R1                mp.[℃]
1              O-CH3                  n-C5H11
2              O-CH2-CH2-S-C6H5   CH3
3              O-CH2-CO-C(CH3)3    CH3
4              H                       CH2-O-CH2-C6H5
5              H                       CH2-S-CH3
6              H                       CH2-SO2-C6H5
7              H                       CH2-S-C6H5
8              O-CH3                  CH2-S-C6H5
9              O-CH2-O-CH2-C6H5   CH3
10             O-CH2-O-C6H5        CH3
11             H                       OH
                     制剂
浓缩乳液
活性化合物              200克/升
乙氧基化的蓖麻油        100克/升
四氢糖醇                793克/升
                   生物试验结果
用下述试验检测本发明组合物和化合物的杀真菌活性。
a)抗谷类白粉病(大麦白粉病和小麦白粉病)活性
本试验测试当用于叶面喷洒时试验用组合物和化合物的预防活性。使谷类秧苗(大麦品种：Golden Promise；小麦品种：Kanzler)长至一叶期。然后用试验用化合物的水溶液喷洒，该喷洒液由含5,000ppm TRITON_×155(一种非离子型聚氧亚乙基醚表面活性剂)的在丙酮中的5,000ppm储备液配制。用带喷雾嘴的自动喷洒线处理植物。喷洒体积为20ml。处理后1～3天，通过在秧苗上面摇动带形成孢子的病原体(大麦——大麦白粉病菌；小麦——小麦白粉病菌)的储备培养植物，使秧苗接种白粉病。然后，在不使空气流动的情况下保持植物3小时，以使孢子停落在叶面上。接着，将植物保持于温室中直至症状出现。以害病叶面积与对照植物的害病叶面积的百分比作为评估基准。
b)抗苹果白粉病(Podosphaera leucotricha)活性
本试验测定当用于叶面喷洒时试验用组合物和化合物的预防活性。使苹果秧苗(品种：Morgenduft)长至6～7叶期，然后切至剩3叶，去掉老叶和嫩叶。用试验用化合物在水中的溶液(20ml)喷洒植物，该喷洒液由含5,000pm TRITON_×155的在丙酮中的5,000ppm储备液配制。用带喷雾嘴的自动喷洒线处理植物。处理后1～3天，通过在秧苗上面摇动带形成孢子的病原体的储备培养植物使秧苗接种白粉病。然后，在不使空气流动的情况下保持植物3小时。接着，将植物保持在温室直至症状出现。以处理过的植物的害病叶面积与对照植物的害病叶面积的百分比作为评估基准。
c)抗葡萄白粉病(Uncinula necator)活性
本试验测定当用于叶面喷洒时，试验用组合物和化合物的直接预防活性。使葡萄藤(品种：Müller-Thurgau)的插条长至6～8叶期，然后切剩4片相等大小的叶子。用喷雾器将试验用化合物在水中的溶液(20ml)全部喷洒在植物上，该喷洒液由含5,000ppm TRI-TON_×155的在丙酮中的5,000ppm储备液配制。处理后2天，插条在一专用的孢子沉落塔中用葡萄白粉病菌的无性芽胞接种。将孢子从新形成孢子的葡萄叶(葡萄白粉病菌(U.necator)储备培养物)吹入沉落塔的上面的孔，使其停落在叶上5分钟。然后，以夜间12小时、白昼12小时的间隔将植物于18℃(夜间)和22℃(白昼)保持在人工气候室中。用荧光灯以11,200勒克司的强度照射。21天后，通过肉眼检测和以三片最嫩的叶子的害病叶面与对照植物的害病叶面积的百分比为基准，进行评估。试验结果见下表A和B，其中，化合物可通过参照上述实施例1～9中或表4～10中的化合物编号而加以识别。无评估者表示未进行上述试验中的任一种。评估0表示害病状况与未处理的对照组相同，评估100表示未害病。
                               表A
                       白粉病            苹果白粉病   葡萄白粉病
                 大麦         小麦
    化合物No.    100ppm       100ppm       100ppm       200ppm
      *1        100          100            96           84
      *2        99           100            0            41
      *3        0            0              0
        4        95           100            41
        5        94           99             41
        6        99           100
      *8        100          100            100          95
                            表A(续)
                     白粉病          苹果白粉病    葡萄白粉病
               大麦        小麦
   化合物No.    100ppm      100ppm      100ppm        200ppm
       *9      0           70          95
       *10     85          100         44            88
       *11     0           0           0
       *12     23          0           0
         13     87          100
       *14     0           36          0
       *15     99          73          0
         16     100         94
         17     25          5           77
         18     89          57          73
         19     19          26          15
         20     100         10          0             28
         21     9           19          15
         23     100         100         100
         24     94          100         53
         26     82          79          33
         27     90          100         89
         28     100         98
         29     99          93          97
         31     99          100
         32     1           28          8
         33     39          98
         34     0           0
                             表A(续)
                   白粉病             苹果白粉病    葡萄白粉病
             大麦         小麦
 化合物No.   100ppm       100ppm        100ppm        200ppm
       35    0            22            9
       36    49           61
       37    70           37
       38    42           77
       39    28           85
       40    100          100
       41    49           99
       43    23           49
       44    89           38            10
       46    100          100
       47    95           100
       48    84           90            100
       50    4            6             94
       51    51           25
       52    0            0
       53    100          100
     *54    100          100
       56    100          100           11
     *57    99           100
     *58    100          100
     *59    0            1
       60    0            32
       62    100          100
                                 表A(续)
                       白粉病            苹果白粉病  葡萄白粉病
                大麦          小麦
    化合物No.   100ppm        100ppm       100ppm      200ppm
      *64       95            99           71          63
      *66       0             0            0
      *67       43            0            0
      *68       0             0            0
      *69       0             28           0
      *71       99            32           10
      *72       55            72           0
      *73       99            94           26          33
      *74       0             0            16
      *75       61            34           0
        76       33            57
      *77       41            99           90
      *78       0             85           0
      *79       0             0            0
        80       76            100
        82       100           100
        84       0             0
        85       33            28
        86       0             17
        91       93            100
      *93       0             17
      *94       0             0
      *95       91            0
                            表A(续)
                   白粉病            苹果白粉病  葡萄白粉病
             大麦         小麦
  化合物No.  100ppm       100ppm      100ppm      200ppm
     *96     100          100         100
     *97     100          100         100
     *98     100          100         100
     *99     86           6           29
    *100     100          100         100
    *101     100          100         87
    *102     100          100         100
    *103     100          100         10
    *104     100          14          27
    *105     100          100         100
    *106     100          100
    *107     0            21
    *108     100          100
    *109     100          100
    *110     100          100
    *111     95           100
    *112     0            19
    *113     0            28
    *114     0            17
    *115     100          60
    *116     100          64
    *117     100          100         6
                           表A(续)
                   白粉病          苹果白粉病   葡萄白粉病
             大麦        小麦
   化合物No. 100ppm      100ppm      100ppm       200ppm
     *118   99          13          66
     *119   100         89          98
     *120   100         89          46
     *121   100         100         37
     *122   100         100         28
     *123   0           44          9
     *124   100         100         89
     *125   100         28          8
     *126   100         100         100
     *127   100         100         100
     *128   100         100         100
     *129   100         100         100
     *130   0           78          0
     *131   100         100         100
     *132   100         100         100
     *133   100         100         100
     *134   100         100         100
     *135   100         100         100
     *136   100         100         100
     *137   100         100         97
     *138   100         100         100
                          表A(续)
化合物           白粉病          苹果白粉病    葡萄白粉病
No.        大麦        小麦
           100ppm      100ppm      100ppm       200ppm
*139      100         100         100
*140      100         100         100
*141      97          100         0
*142      97          100         53
*143      100         100         100
*144      100         100         100
*145      84          97          80
*146      65          91
*147      100         100
*148      100         100
*149      39          66
*161      48          77          100
*162      23          4           100
*163      97          90          7
 166       100         100         --
 167       100         97          20
 168       100         100         2
 169       100         100         0
 170       100         100         100
 171       97          100         0
 172       100         97          100
 173       26          53          0
                               表A(续)
                      白粉病           苹果白粉病    葡萄白粉病
               大麦         小麦
化合物No.      100ppm       100ppm       100ppm        200ppm
      174      100          100          98
      175      100          100          100
      176      0            0            8
      177      52           0            0
      178      100          100          100
      180      95           19           --
      181      5            0            6
      182      100          93           0
      183      100          74           0
      184      100          100          100
      185      0            0            0
      186      0            100          100
      189      100          100          100
      190      98           8            68
      191      100          100          99
      196      0            82           87
      197      71           78           1
      199      0            0            --
      200      100          100          41
      201      98           0            --
      202      0            92           92
*表示处理72小时后，用谷类白粉病菌和苹果白粉病菌进行感染。
                             表B
                      白粉病            苹果白粉病
化合物           大麦        小麦
表/No.           100ppm      100ppm       100ppm
表4/1            100         100          ---
2                100         100          0
3                100         100          48
4                51          100          5
5                11          25           ---
6                26          23           ---
7                100         100          ---
8                95          92           ---
9                98          100          ---
10               100         100          0
11               100         100          6
                      表B(续)
                   白粉病             苹果白粉病
化合物      大麦          小麦
表/No.      100ppm        100ppm        100ppm
12          96            100           0
13          100           90            0
表5/1       100           100           97
2           100           99            63
3           100           100           25
4           100           100           0
表6/1       100           100           100
2           100           100           100
3           100           100           100
4           100           100           100
5           100           100           100
6           100           100           100
7           100           45            0
8           100           100           100
9           74            23            6
10          100           100           96
11          100           100           100
12          100           0             0
表6/13      100           100           100
16          100           100           100
17          100           58            100
18          100           97            100
19          100           100           100
20          100           100           100
21          100           100           38
                           表B(续)
                    白粉病            苹果白粉病
化合物       大麦          小麦
表/No.       100ppm        100ppm       100ppm
22           100           100          100
23           100           95           19
25           100           100          100
表7/3        100           100          93
4            100           100          100
表9/1        100           100          100

Claims (6)

1.一种控制植物病原体性真菌和由此引起的疾病的方法，其特征在于，它包括使上述真菌与有效杀真菌量的具有式I所示结构的二苯甲酮类化合物接触，
所述具有式I所示的结构的化合物选自
2，3，5，6-四甲基-4′，5′，6′-三甲氧基-2′-甲基二苯甲酮；
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮-O-甲肟；
2，6-二氯-5′-叔丁氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′，6′-二正丁氧基-4′-甲氧基-2′-甲基二苯甲酮；
2′-烯丙氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-苄氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-丁氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-环己基甲氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-苯甲酰氧基甲氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2′-环戊基氧基-2，6-二氯-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′3′，4′-三甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′-乙氧基-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′-庚氧基-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-2′-己氧基-3′，4′-二甲氧基-6′-甲基二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-2′-(2-甲氧基-乙氧基)-6′-甲基二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-(3-甲基丁氧基)二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-(丙-2-炔基氧基)二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-戊氧基二苯甲酮；
2，6-二氯-3′，4′-二甲氧基-6′-甲基-2′-丙氧基二苯甲酮；
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-(3-甲基丁氧基)二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-(丙-2-炔基氧基)二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-辛氧基二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-戊氧基二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-丙氧基二苯甲酮；
2，6-二氯-4′-甲氧基-2′-甲基-5′-三甲基硅烷基甲氧基二苯甲酮；
2，6-二氯-5′-(1-乙基-丙氧基)-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-二氟甲氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-乙氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-庚氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-己氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-4′，5′-二甲氧基-2′-甲基二苯甲酮-O-正丙肟；
2，6-二氯-5′-异丁氧基-4′-甲氧基-2′-甲基二苯甲酮；
2，6-二氯-5′-异丙氧基-4′-甲氧基-2′-甲基二苯甲酮；
5′-丁氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环己基甲氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环己基氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环戊基氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；
5′-环丙基甲氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮；或
5′-癸氧基-2，6-二氯-4′-甲氧基-2′-甲基二苯甲酮。
2.具有下式所示结构的化合物，
Figure C9610101400041
式中，Q表示氢或氯原子；R表示氢原子、C3-C8环烷氧基或可被一个或多个氟原子或一个苯基、苯氧基、苯硫基或苄氧基任意取代的C1-C8烷氧基，其中的苯基部分可被卤原子、C1-C4烷基、C1-C4烷氧基三氟甲基和/或三氟甲氧基取代；R′表示氢或可被一或多个卤原子、C1-C4烷氧基、苯基、苯氧基或苯硫基取代的C1-C10烷基，其中的苯基部分可被卤原子、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基取代；条件是：当Q和R表示氢时，R′不可以是甲基。
3.具有下式所示结构的化合物：
Figure C9610101400051
其中，Q和Q′独立地表示氢原子或甲基；R表示氢原子、C3-C8环烷氧基或可被一个或多个氟原子、苯基、苯氧基、苯硫基或苄氧基任意取代的C1-C8烷氧基，其中的苯基部分可被一或多个卤原子、C1-C4烷基、C1-C4烷氧基、三氟甲基或三氟甲氧基取代；R1表示氢或可被一或多个卤原子、C1-C4烷氧基、苯基、苯氧基或苯硫基任意取代的C1-C10烷基，其中的苯基部分可被一或多个卤原子、C1-C4烷基、C1-C4烷氧基、三氟甲基或三氟甲氧基取代。
4.一种杀真菌组合物，其特征在于，它包括农业上可接受的载体和有效杀真菌量的式I所示结构的化合物，
Figure C9610101400052
式中，X表示氧原子或基团NOR；Y表示氧原子；R1、R2、R3和R4分别独立地表示卤原子或C1-C6烷基；R5和R6分别独立地表示C1-C6烷氧基；m表示整数1或3，n表示0或整数1。
5.一种制备式1所示结构的化合物的方法，
Figure C9610101400061
式中，X表示氧原子，R1、R2、R3、R4、R5、R6、Y、m和n的定义与权利要求1中的相同，
其特征在于，它包括将式II所示化合物
Figure C9610101400062
与式III所示化合物反应，
Figure C9610101400063
式中，R1、R2、R3、R4、R5、R6、Y、m和n的定义与权利要求1中的相同，Z1和Z2中的一个表示氢原子，另一个表示基团COCl或一个表示卤化镁基团MgHal，另一个表示COCl，所示Hal表示溴或碘原子。
6.一种制备式Ib所示结构的化合物的方法，
Figure C9610101400071
式中，X表示基团NOH；m表示0或整数1、2或3；Y表示氧原子；R4表示甲基；R5表示甲氧基，R3、R6和n的定义与权利要求1中的相同，
其特征在于，它包括将式VI所示化合物
与至少1摩尔当量的式VII所示化合物
Figure C9610101400073
在至少1摩尔当量的氯化铝和非极性溶剂的存在下反应，生成中间体，再将该中间体在酸和水的存在下水解，得到产物即式Ib化合物。
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CZ294096B6 (cs) 2004-10-13
HU9600116D0 (en) 1996-03-28
DE69635363D1 (de) 2005-12-08
DE69635363T2 (de) 2006-07-27
BR9600165A (pt) 1998-01-06
SK285301B6 (sk) 2006-10-05
EP0727141A3 (en) 1998-01-28
RO117827B1 (ro) 2002-08-30
CA2167550A1 (en) 1996-07-21
JPH08277243A (ja) 1996-10-22
HUP9600116A3 (en) 1999-03-01
ES2248803T3 (es) 2006-03-16
AU4209196A (en) 1996-08-01
EP0727141A2 (en) 1996-08-21
IL116818A (en) 2006-12-31
TW391957B (en) 2000-06-01
IL116818A0 (en) 1996-05-14
CZ8996A3 (en) 1996-08-14
SK7496A3 (en) 1996-11-06
EP0727141B1 (en) 2005-11-02
JP3895795B2 (ja) 2007-03-22
ATE308241T1 (de) 2005-11-15
DK0727141T3 (da) 2006-01-16
HU225219B1 (en) 2006-08-28
HUP9600116A2 (en) 1996-11-28

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