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CN1603299A - Novel carboxylate herbicides - Google Patents

Novel carboxylate herbicides Download PDF

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CN1603299A
CN1603299A CN 03143375 CN03143375A CN1603299A CN 1603299 A CN1603299 A CN 1603299A CN 03143375 CN03143375 CN 03143375 CN 03143375 A CN03143375 A CN 03143375A CN 1603299 A CN1603299 A CN 1603299A
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alkyl
halo
thiazolinyl
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alkynyl
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CN1281602C (en
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刘长令
聂开晟
秦宵然
耿丽文
张宗俭
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
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Abstract

本发明涉及新型羧酸酯类化合物及其组合物和用这些化合物防除杂草的使用方法，含有这些化合物的除草剂可用于防除小麦、玉米、大豆、棉花、花生、蔬菜和水稻等田中的杂草。新型羧酸酯类化合物可用通式I表示。

Figure 03143375

The present invention relates to novel carboxylate compounds and their compositions and methods for using these compounds to control weeds. Herbicides containing these compounds can be used to control weeds in fields such as wheat, corn, soybeans, cotton, peanuts, vegetables and rice. Grass. Novel carboxylate compounds can be represented by general formula I.

Figure 03143375

Description

新型羧酸酯类除草剂New Carboxylate Herbicides

技术领域technical field

本发明属于农用除草剂领域。涉及的是一类新型羧酸酯类化合物及组合物、它们的用途及使用方法。The invention belongs to the field of agricultural herbicides. It relates to a class of novel carboxylate compounds and compositions, their application and application method.

背景技术Background technique

杂草对作物、尤其是对于能够满足人类基本需求的粮食和纤维等农产品，如棉花，水稻，玉米，小麦，大豆等造成很大的损害。杀死或抑制杂草生长的同时避免或减少对作物的损害是一种改进农业生产的有效途径。因此需要不断开发更有效的新型除草剂。羧酸酯类化合物如精喹禾灵等是已知的除草剂，但本发明的新型羧酸酯类化合物未见文献报导。Weeds cause great damage to crops, especially agricultural products such as grain and fiber that can meet basic human needs, such as cotton, rice, corn, wheat, soybeans, etc. Killing or inhibiting the growth of weeds while avoiding or reducing damage to crops is an effective way to improve agricultural production. Therefore, there is a need to continuously develop new and more effective herbicides. Carboxylate compounds such as quizalofop-p-ethyl are known herbicides, but the novel carboxylate compounds of the present invention have not been reported in literature.

发明内容Contents of the invention

为了满足农业上的要求，本发明提供了一种新型羧酸酯类化合物及其防除杂草的使用方法和含有这些化合物的除草剂在农业上的应用。作为除草剂，可以有效控制小麦、玉米、大豆、棉花、花生、蔬菜和水稻等田中的杂草，并且对这些作物安全。In order to meet the requirements of agriculture, the present invention provides a novel carboxylate compound, its use method for controlling weeds and the agricultural application of the herbicide containing these compounds. As a herbicide, it can effectively control weeds in fields such as wheat, corn, soybean, cotton, peanut, vegetables and rice, and is safe for these crops.

本发明提出的新型羧酸酯类化合物，如通式I所示：The novel carboxylate compound that the present invention proposes, as shown in general formula I:

Figure A0314337500081
Figure A0314337500081

式中：In the formula:

X-X1-Z选自以下基团之一：XX 1 -Z is selected from one of the following groups:

CH2CH2R1，CH2CO-R1，CH2CH2SR1， CH2CH2R1 , CH2CO - R1 , CH2CH2SR1 ,

Figure A0314337500083
Figure A0314337500083

当-X-选自CH2CH2OCH2CH2，CH2CH2SCH2CH2，CH2CH2N(CH3)CH2CH2，When -X- is selected from CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 SCH 2 CH 2 , CH 2 CH 2 N(CH 3 )CH 2 CH 2 ,

Figure A0314337500091
Figure A0314337500091

CH2CH2，CH2CH2SO2CH2CH2或CH2CH2SOCH2CH2时，X1选自O，Z选自Q；CH 2 CH 2 , CH 2 CH 2 SO 2 CH 2 CH 2 or CH 2 CH 2 SOCH 2 CH 2 , X 1 is selected from O, Z is selected from Q;

其中：in:

R1、R2可相同或不同，分别选自H，卤素，CN，CO2R3，CONR2R3，CHR2CO2R3，CHR2CONR2R3，C1-C12烷基，环C3-C8烷基，C2-C12烯基，环C3-C8烯基，C2-C12炔基，卤代C1-C12烷基，卤代C2-C12烯基，卤代C2-C12炔基，C1-C12烷氧基，C1-C12烷硫基，C1-C12烷基磺酰基C1-C12烷基，C1-C12烷基亚磺酰基C1-C12烷基，C1-C12烷基磺酰基环C3-C8烷基，C1-C12烷基亚磺酰环C3-C8烷基，氰基C1-C12烷氧基，氰基C1-C12烷基，氰基环C3-C8烷基，卤代C1-C12烷氧基，卤代C1-C12烷硫基，卤代环C3-C8烷，芳基，杂芳基，芳基C1-C12烷基或杂芳基C2-C12烷基，所有这些基团都可以被下述基团进行1-3次取代：溴，氯，氟，C1-C12烷基，环C3-C8烷基，C2-C12烯基，环C3-C8烯基，C2-C12炔基，卤代C1-C12烷基，卤代C2-C12烯基，卤代C2-C12炔基，C1-C12烷氧基，C1-C12烷硫基，C1-C12烷基磺酰基，C1-C12烷基亚磺酰基，苯基，苯代C1-C12烷基，苯代C2-C12烯基，苯代C2-C12炔基，氰基或卤代C1-C12烷氧基，所有这些基团还可以被进一步取代；R 1 and R 2 can be the same or different, and are selected from H, halogen, CN, CO 2 R 3 , CONR 2 R 3 , CHR 2 CO 2 R 3 , CHR 2 CONR 2 R 3 , C 1 -C 12 alkyl , cycloC 3 -C 8 alkyl, C 2 -C 12 alkenyl, cyclo C 3 -C 8 alkenyl, C 2 -C 12 alkynyl, halogenated C 1 -C 12 alkyl, halogenated C 2 - C 12 alkenyl, halogenated C 2 -C 12 alkynyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl C 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl C 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl ring C 3 -C 8 alkyl, C 1 -C 12 alkylsulfinyl ring C 3 - C 8 alkyl, cyano C 1 -C 12 alkoxy, cyano C 1 -C 12 alkyl, cyano ring C 3 -C 8 alkyl, halo C 1 -C 12 alkoxy, halo C 1 -C 12 alkylthio, halogenated ring C 3 -C 8 alkane, aryl, heteroaryl, aryl C 1 -C 12 alkyl or heteroaryl C 2 -C 12 alkyl, all of these Each group can be substituted 1-3 times by the following groups: bromine, chlorine, fluorine, C 1 -C 12 alkyl, cyclo C 3 -C 8 alkyl, C 2 -C 12 alkenyl, cyclo C 3 - C 8 alkenyl, C 2 -C 12 alkynyl, halogenated C 1 -C 12 alkyl, halogenated C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkynyl, C 1 -C 12 alkoxy radical, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylsulfinyl, phenyl, phenyl C 1 -C 12 alkyl, phenyl C 2 - C 12 alkenyl, phenyl C 2 -C 12 alkynyl, cyano or halo C 1 -C 12 alkoxy, all of which can be further substituted;

R3和R4相同或不同，分别选自H，CO2R3，CONR2R3，CHR2CO2R3，CHR2CONR2R3，C1-C12烷基，环C3-C8烷基，C2-C12烯基，环C3-C8烯基，C2-C12炔基，卤代C1-C12烷基，卤代C2-C12烯基，卤代C2-C12炔基，C1-C12烷氧基，C1-C12烷硫基，C1-C12烷基磺酰基C1-C12烷基，C1-C12烷基亚磺酰基C1-C12烷基，C1-C12烷基磺酰基环C3-C8烷基，C1-C12烷基亚磺酰环C3-C8烷基，氰基C1-C12烷氧基，氰基C1-C12烷基，氰基环C3-C8烷基，卤代C1-C12烷氧基，卤代C1-C12烷硫基，卤代环C3-C8烷，芳基，杂芳基，芳基C1-C12烷基或杂芳基C2-C12)基，所有这些基团都可以被下述基团进行1-3次取代：溴，氯，氟，C1-C12烷基，环C3-C8烷基，C2-C12烯基，环C3-C8烯基，C2-C12炔基，卤代C1-C12烷基，卤代C2-C12烯基，卤代C2-C12炔基，C1-C12烷氧基，C1-C12烷硫基，C1-C12烷基磺酰基，C1-C12烷基亚磺酰基，苯基，取代苯基、苯代C1-C12烷基，苯代C2-C12烯基，苯代C2-C12炔基，氰基或卤代C1-C12烷氧基，所有这些基团还可以被进一步取代；R 3 and R 4 are the same or different, respectively selected from H, CO 2 R 3 , CONR 2 R 3 , CHR 2 CO 2 R 3 , CHR 2 CONR 2 R 3 , C 1 -C 12 alkyl, ring C 3 - C 8 alkyl, C 2 -C 12 alkenyl, cycloC 3 -C 8 alkenyl, C 2 -C 12 alkynyl, halogenated C 1 -C 12 alkyl, halogenated C 2 -C 12 alkenyl, Halo C 2 -C 12 alkynyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl C 1 -C 12 alkyl, C 1 -C 12 alkyl Alkylsulfinyl C 1 -C 12 alkyl, C 1 -C 12 alkylsulfinyl ring C 3 -C 8 alkyl, C 1 -C 12 alkylsulfinyl ring C 3 -C 8 alkyl, Cyano C 1 -C 12 alkoxy, cyano C 1 -C 12 alkyl, cyanocyclo C 3 -C 8 alkyl, halo C 1 -C 12 alkoxy, halo C 1 -C 12 Alkylthio, halocyclic C 3 -C 8 alkane, aryl, heteroaryl, aryl C 1 -C 12 alkyl or heteroaryl C 2 -C 12 ) group, all of which can be represented by 1-3 substitutions of the above groups: bromine, chlorine, fluorine, C 1 -C 12 alkyl, cyclo C 3 -C 8 alkyl, C 2 -C 12 alkenyl, cyclo C 3 -C 8 alkenyl, C 2 -C 12 alkynyl, halogenated C 1 -C 12 alkyl, halogenated C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkynyl, C 1 -C 12 alkoxy, C 1 - C 12 alkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylsulfinyl, phenyl, substituted phenyl, phenyl C 1 -C 12 alkyl, phenyl C 2 -C 12 alkenyl, phenyl C 2 -C 12 alkynyl, cyano or halo C 1 -C 12 alkoxy, all of which can be further substituted;

NR3R4、NR2R3可分别组成五圆或六圆环；或者还可为NR 3 R 4 , NR 2 R 3 can respectively form a five-circle or six-circle ring; or can also be

其中：R5为R1，R6为R2；R5和R6还可以组成五圆或六圆环；Among them: R 5 is R 1 , R 6 is R 2 ; R 5 and R 6 can also form five or six rings;

Q选自Q1，Q2，Q3，Q4，Q5，Q6，Q7，Q8，Q9，Q10，Q11，Q12或Q13：(结构中R表示旋光异构体R构型)Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13: (R in the structure represents the configuration of the optical isomer R)

本发明中的″芳基″指的是单环或多环化合物，如苯，萘，茚，蒽，双环戊二烯并对二氢苯，芴，苊，菲和甘菊环。"Aryl" in the present invention refers to monocyclic or polycyclic compounds such as benzene, naphthalene, indene, anthracene, dicyclopentadienal, fluorene, acenaphthene, phenanthrene and azulene.

″杂芳基″指的是单环或多环的呋喃，噻吩，吡咯，异恶唑，恶唑，异噻二唑，噻唑，吡唑，咪唑，1，2，3-三唑，1，1，4-三唑，四唑，1，2，3-噻二唑，1，1，4-噻二唑，1，3，4-噻二唑，1，2，3-噻二唑，1，1，4-噻二唑，1，3，4-噻二唑，吡啶，哒嗪，嘧啶，吡嗪，1，3，5-三嗪，1，1，4-三嗪，1，1，4，5-四嗪，苯并呋喃，苯并噻吩，吲哚，苯并异恶唑，苯并恶唑，苯并异噻唑，苯并噻唑，苯并吡唑，苯并咪唑，苯并三唑，1，2-亚甲基二氧基苯，1，2-亚乙基二氧基苯，喹啉和异喹啉。"Heteroaryl" refers to monocyclic or polycyclic furan, thiophene, pyrrole, isoxazole, oxazole, isothiadiazole, thiazole, pyrazole, imidazole, 1,2,3-triazole, 1, 1,4-triazole, tetrazole, 1,2,3-thiadiazole, 1,1,4-thiadiazole, 1,3,4-thiadiazole, 1,2,3-thiadiazole, 1,1,4-thiadiazole, 1,3,4-thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,1,4-triazine, 1, 1,4,5-tetrazine, benzofuran, benzothiophene, indole, benzisoxazole, benzoxazole, benzisothiazole, benzothiazole, benzopyrazole, benzimidazole, benzo triazole, 1,2-methylenedioxybenzene, 1,2-ethylenedioxybenzene, quinoline and isoquinoline.

“烷基”包括支链和直链的烷基基团。典型的烷基有甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、异戊基、正己基、正庚基、异辛基、壬基、癸基、十一烷基、十二烷基及其它。"Alkyl" includes both branched and straight chain alkyl groups. Typical alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, Isooctyl, Nonyl, Decyl, Undecyl, Dodecyl and others.

“环烷基”指的是含脂肪族环结构的化合物，如环丙烷、环丁烷、环戊烷、环己烷、环庚烷、环辛烷及其它。"Cycloalkyl" refers to compounds containing an aliphatic ring structure, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and others.

“卤代烷”指的是一个或多个卤素基团取代烷基。"Haloalkyl" means one or more halo radicals substituted for an alkyl group.

“卤素”指的是氟、氯、溴或碘。"Halogen" refers to fluorine, chlorine, bromine or iodine.

“烷基磺酰烷基”指的是烷基磺酰基(烷基-SO2)取代烷基，如甲基磺酰甲基。"Alkylsulfonylalkyl" refers to an alkylsulfonyl (alkyl- SO2 ) substituted alkyl group, such as methylsulfonylmethyl.

“烷基亚磺酰烷基”指的是烷基亚磺酰基(烷基-SO)取代烷基，如甲基亚磺酰甲基。"Alkylsulfinylalkyl" refers to an alkylsulfinyl (alkyl-SO) substituted alkyl group, such as methylsulfinylmethyl.

“烯基”指的是不饱和的碳氢基团，直链或支链上含有一个或两个双键。"Alkenyl" refers to an unsaturated hydrocarbon group containing one or two double bonds in a straight or branched chain.

“环烯基”指的是脂肪族环含有一个或两个双键，如环戊烯、环己烯，1，4-环己烯及其它。"Cycloalkenyl" means an aliphatic ring containing one or two double bonds, such as cyclopentene, cyclohexene, 1,4-cyclohexene and others.

“卤代烯”指的是一个或多个卤素取代烯基。“炔基”指的是不饱和的碳氢基团，直链或支链中含有一个或两个三键。"Haloalkene" means one or more halogen substituted alkenyl groups. "Alkynyl" refers to an unsaturated hydrocarbon group containing one or two triple bonds in a straight or branched chain.

“芳烷基”指的是烷基基团支链或直链中被芳基取代所形成的含有芳基的部分称为芳烷基。"Aralkyl" refers to the aryl-containing part formed by substituting the branched or straight chain of an alkyl group with an aryl group, which is called an aralkyl group.

“杂芳烷基”指的是烷基基团支链或直链中被杂芳基取代所形成的含有芳基的部分称为芳烷基。"Heteroaralkyl" refers to the aryl-containing part formed by substituting a branched or straight chain of an alkyl group with a heteroaryl group, which is called an aralkyl group.

“烷氧基”指的是支链或直链中的烷基连有氧原子，典型的烷氧基有甲氧基、乙氧基、正丙氧基、异丙氧基、叔丁氧基及其它。"Alkoxy" refers to a branched or linear alkyl group with an oxygen atom attached. Typical alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, and tert-butoxy and others.

“卤代烷氧基”指的是一个或多个卤素原子取代烷氧基。"Haloalkoxy" means an alkoxy group in which one or more halogen atoms are substituted.

“烷硫基”指的是支链或直链中的烷基连有硫原子。"Alkylthio" refers to a branched or straight chain alkyl group to which a sulfur atom is attached.

“卤代烷硫基”指的是一个或多个卤素原子取代烷硫基。"Haloalkylthio" means an alkylthio group substituted with one or more halogen atoms.

本发明中进一步优选的化合物为通式化合物I中：X-X1-Z选自以下基团之一：Further preferred compounds in the present invention are compounds of the general formula I: XX 1 -Z is selected from one of the following groups:

Figure A0314337500111
CH2CH2R1，CH2CO-R1，CH2CH2SR1，
Figure A0314337500111
CH2CH2R1 , CH2CO - R1 , CH2CH2SR1 ,

当-X-选自CH2CH2OCH2CH2，CH2CH2SCH2CH2，CH2CH2N(CH3)CH2CH2，When -X- is selected from CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 SCH 2 CH 2 , CH 2 CH 2 N(CH 3 )CH 2 CH 2 ,

Figure A0314337500121
Figure A0314337500121

CH2CH2，CH2CH2SO2CH2CH2或CH2CH2SOCH2CH2时，X1选自O，Z选自Q。When CH 2 CH 2 , CH 2 CH 2 SO 2 CH 2 CH 2 or CH 2 CH 2 SOCH 2 CH 2 , X 1 is selected from O, and Z is selected from Q.

其中：in:

R1、R2可相同或不同，分别选自H，溴，氯，氟，CN，CO2R3，CONR2R3，CHR2CO2R3，CHR2CONR2R3，C1-C6烷基，环C5-C6烷基，C2-C6烯基，环C3-C8烯基，C2-C6炔基，卤代C1-C6烷基，卤代C2-C6烯基，卤代C2-C6炔基，C1-C6烷氧基，C1-C6烷硫基，芳基，杂芳基，芳基C1-C12烷基或杂芳基C2-C12烷基，其中芳基或杂芳基为呋喃，萘，苯基，吡唑，吡啶，嘧啶，噻吩或三唑；芳基或杂芳基可被下述基团进行1-3次取代：溴，氯，氟，C1-C12烷基，环C3-C8烷基，C2-C12烯基，环C3-C8烯基，C2-C12炔基，卤代C1-C12烷基，卤代C2-C12烯基，卤代C2-C12炔基，C1-C12烷氧基，C1-C12烷硫基，C1-C12烷基磺酰基，C1-C12烷基亚磺酰基，苯基，苯代C1-C12烷基，苯代C2-C12烯基，苯代C2-C12炔基，氰基或卤代C1-C12烷氧基，所有这些基团还可以被进一步取代；R 1 and R 2 may be the same or different, and are selected from H, bromine, chlorine, fluorine, CN, CO 2 R 3 , CONR 2 R 3 , CHR 2 CO 2 R 3 , CHR 2 CONR 2 R 3 , C 1 - C 6 alkyl, cyclo C 5 -C 6 alkyl, C 2 -C 6 alkenyl, cyclo C 3 -C 8 alkenyl, C 2 -C 6 alkynyl, halogenated C 1 -C 6 alkyl, halo Substituted C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, aryl, heteroaryl, aryl C 1 -C 12 Alkyl or heteroaryl C 2 -C 12 alkyl, wherein aryl or heteroaryl is furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene or triazole; aryl or heteroaryl can be The following groups are substituted 1-3 times: bromine, chlorine, fluorine, C 1 -C 12 alkyl, cyclo C 3 -C 8 alkyl, C 2 -C 12 alkenyl, cyclo C 3 -C 8 alkenyl , C 2 -C 12 alkynyl, halogenated C 1 -C 12 alkyl, halogenated C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkynyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylsulfinyl, phenyl, phenyl C 1 -C 12 alkyl, phenyl C 2 -C 12 alkenyl , phenylated C 2 -C 12 alkynyl, cyano or halogenated C 1 -C 12 alkoxy, all of these groups can be further substituted;

R3和R4可相同或不同，分别选自H，CO2R3，CONR2R3，CHR2CO2R3，CHR2CONR2R3，C1-C6烷基，环C5-C6烷基，C2-C6烯基，环C3-C8烯基，C2-C6炔基，卤代C1-C6烷基，卤代C2-C6烯基，卤代C2-C6炔基，C1-C6烷氧基，C1-C6烷硫基，芳基，杂芳基，芳基C1-C12烷基或杂芳基C2-C12烷基，其中芳基或杂芳基为呋喃，萘，苯基，吡唑，吡啶，嘧啶，噻吩或三唑，芳基或杂芳基可被下述基团进行1-3次取代：溴，氯，氟，C1-C12烷基，环C3-C8烷基，C2-C12烯基，环C3-C8烯基，C2-C12炔基，卤代C1-C12烷基，卤代C2-C12烯基，卤代C2-C12炔基，C1-C12烷氧基，C1-C12烷硫基，C1-C12烷基磺酰基，C1-C12烷基亚磺酰基，苯基，苯代C1-C12烷基，苯代C2-C12烯基，苯代C2-C12炔基，氰基或卤代C1-C12烷氧基，所有这些基团还可以被进一步取代。R 3 and R 4 may be the same or different, respectively selected from H, CO 2 R 3 , CONR 2 R 3 , CHR 2 CO 2 R 3 , CHR 2 CONR 2 R 3 , C 1 -C 6 alkyl, ring C 5 -C 6 alkyl, C 2 -C 6 alkenyl, cycloC 3 -C 8 alkenyl, C 2 -C 6 alkynyl, halogenated C 1 -C 6 alkyl, halogenated C 2 -C 6 alkenyl , Halo C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, aryl, heteroaryl, aryl C 1 -C 12 alkyl or heteroaryl C 2 -C 12 alkyl, wherein aryl or heteroaryl is furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene or triazole, aryl or heteroaryl can be carried out by the following groups 1-3 Secondary substitution: bromine, chlorine, fluorine, C 1 -C 12 alkyl, cyclo C 3 -C 8 alkyl, C 2 -C 12 alkenyl, cyclo C 3 -C 8 alkenyl, C 2 -C 12 alkynyl , halogenated C 1 -C 12 alkyl, halogenated C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkynyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylsulfinyl, phenyl, phenyl C 1 -C 12 alkyl, phenyl C 2 -C 12 alkenyl, phenyl C 2 -C 12 Alkynyl, cyano or halogenated C 1 -C 12 alkoxy, all of these groups can also be further substituted.

NR3R4、NR2R3可分别组成五圆或六圆环；或者还可为NR 3 R 4 , NR 2 R 3 can respectively form a five-circle or six-circle ring; or can also be

Figure A0314337500122
Figure A0314337500122

其中：R5为R1，R6为R2；R5和R6还可以组成五圆或六圆环；Among them: R 5 is R 1 , R 6 is R 2 ; R 5 and R 6 can also form five or six rings;

Q选自Q1，Q2，Q3，Q4，Q5，Q6，Q7，Q8，Q9，Q10，Q11，Q12或Q13。Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13.

本发明中更进一步优选的化合物为通式化合物I中，X-X1-Z选自以下基团之一：A further preferred compound in the present invention is the compound of general formula I, where XX 1 -Z is selected from one of the following groups:

CH2CH2R1，CH2CO-R1，CH2CH2SR1， CH2CH2R1 , CH2CO - R1 , CH2CH2SR1 ,

当-X-选自CH2CH2OCH2CH2，CH2CH2SCH2CH2，CH2CH2N(CH3)CH2CH2，When -X- is selected from CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 SCH 2 CH 2 , CH 2 CH 2 N(CH 3 )CH 2 CH 2 ,

Figure A0314337500133
Figure A0314337500133

CH2CH2，CH2CH2SO2CH2CH2或CH2CH2SOCH2CH2时，X1选自O，Z选自Q；CH 2 CH 2 , CH 2 CH 2 SO 2 CH 2 CH 2 or CH 2 CH 2 SOCH 2 CH 2 , X 1 is selected from O, Z is selected from Q;

其中：in:

R1、R2可相同或不同，分别选自H，溴，氯，氟，CN，CO2R3，CONR2R3，CHR2CO2R3，CHR2CONR2R3，C1-C6烷基，环C5-C6烷基，C2-C6烯基，环C3-C8烯基，C2-C6炔基，卤代C1-C6烷基，卤代C2-C6烯基，卤代C2-C6)炔基，C1-C6烷氧基，C1-C6烷硫基，芳基，杂芳基，芳基C1-C12烷基或杂芳基C2-C12烷基，其中芳基或杂芳基选自呋喃，苯基或吡啶：芳基或杂芳基可被下述基团进行1-3次取代：溴，氯，氟，C1-C12烷基，环C3-C8烷基，卤代C1-C12烷基，C1-C12烷氧基，C1-C12烷硫基，C1-C12烷基磺酰基，苯基，苯代C1-C12烷基，氰基或卤代C1-C12烷氧基，所有这些基团还可以被进一步取代；R 1 and R 2 may be the same or different, and are selected from H, bromine, chlorine, fluorine, CN, CO 2 R 3 , CONR 2 R 3 , CHR 2 CO 2 R 3 , CHR 2 CONR 2 R 3 , C 1 - C 6 alkyl, cyclo C 5 -C 6 alkyl, C 2 -C 6 alkenyl, cyclo C 3 -C 8 alkenyl, C 2 -C 6 alkynyl, halogenated C 1 -C 6 alkyl, halo Substituted C 2 -C 6 alkenyl, halogenated C 2 -C 6 ) alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, aryl, heteroaryl, aryl C 1 - C 12 alkyl or heteroaryl C 2 -C 12 alkyl, wherein aryl or heteroaryl is selected from furan, phenyl or pyridine: aryl or heteroaryl can be substituted 1-3 times by the following groups : bromine, chlorine, fluorine, C 1 -C 12 alkyl, cycloC 3 -C 8 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio radical, C 1 -C 12 alkylsulfonyl, phenyl, phenyl C 1 -C 12 alkyl, cyano or halo C 1 -C 12 alkoxy, all of which can be further substituted;

R3和R4相同或不同为H，CO2R3，CONR2R3，CHR2CO2R3，CHR2CONR2R3，C1-C6烷基，环C5-C6烷基，C2-C6烯基，环C3-C8烯基，C2-C6炔基，卤代C1-C6烷基，卤代C2-C6烯基，卤代C2-C6炔基，C1-C6烷氧基，C1-C6烷硫基，芳基，杂芳基，芳基C1-C12烷基或杂芳基C2-C12烷基，其中芳基或杂芳基选自呋喃，苯基或吡啶：芳基和杂芳基可被下述基团进行1-3次取代：溴，氯，氟，C1-C12烷基，环C3-C8烷基，卤代C1-C12烷基，C1-C12烷氧基，C1-C12烷硫基，苯基，苯代C1-C12烷基，氰基或卤代C1-C12烷氧基，所有这些基团还可以被进一步取代；R 3 and R 4 are the same or different as H, CO 2 R 3 , CONR 2 R 3 , CHR 2 CO 2 R 3 , CHR 2 CONR 2 R 3 , C 1 -C 6 alkyl, cycloC 5 -C 6 alkane radical, C 2 -C 6 alkenyl, cycloC 3 -C 8 alkenyl, C 2 -C 6 alkynyl, halogenated C 1 -C 6 alkyl, halogenated C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, aryl, heteroaryl, aryl C 1 -C 12 alkyl or heteroaryl C 2 -C 12 Alkyl, where aryl or heteroaryl is selected from furan, phenyl or pyridine: aryl and heteroaryl may be substituted 1-3 times by: bromo, chloro, fluoro, C 1 -C 12 alkane radical, cycloC 3 -C 8 alkyl, halogenated C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, phenyl, phenyl C 1 -C 12 alkane group, cyano group or halogenated C 1 -C 12 alkoxy group, all of which can be further substituted;

NR3R4、NR2R3可分别组成四氢吡咯、吗啉或六氢吡啶；或者还可为NR 3 R 4 , NR 2 R 3 can respectively form tetrahydropyrrole, morpholine or hexahydropyridine; or can also be

Figure A0314337500141
Figure A0314337500141

其中：R5为R1，R6为R2；R5和R6还可以组成环戊烷或环己烷；Wherein: R 5 is R 1 , R 6 is R 2 ; R 5 and R 6 can also form cyclopentane or cyclohexane;

Q选自Q1，Q2，Q3，Q4，Q5，Q6，Q7，Q8，Q9，Q10，Q11，Q12或Q13。Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13.

本发明更为优选的化合物为通式化合物I中，The more preferred compound of the present invention is in compound I of general formula,

X-X1-Z选自：XX 1 -Z selected from:

或 or

当-X-选自：When -X- is selected from:

CH2CH2，CH2CH2OCH2CH2，CH2CH2SCH2CH2 CH2CH2 , CH2CH2OCH2CH2 , CH2CH2SCH2CH2 _ _ _ _ _

或

Figure A0314337500145
or
Figure A0314337500145

时，X1选自O，Z选自Q1，Q3，Q4或Q6；When, X1 is selected from O, Z is selected from Q1, Q3, Q4 or Q6;

其中，R1、R2、R3可相同或不同，分别选自H、C1-C4烷基、苯基、卤代苯基或Wherein, R 1 , R 2 , and R 3 may be the same or different, and are respectively selected from H, C 1 -C 4 alkyl, phenyl, halogenated phenyl, or

本发明由通式I所表示的化合物可通过下述方法制备：The compound represented by general formula I of the present invention can be prepared by the following method:

当X-X1-Z选自以下基团之一时：When XX 1 -Z is selected from one of the following groups:

CH2CH2R1，CH2CO-R1，CH2CH2SR1， CH2CH2R1 , CH2CO - R1 , CH2CH2SR1 ,

Figure A0314337500148
Figure A0314337500148

方法1：method 1:

Figure A0314337500151
Figure A0314337500151

上述中间体II和III中，取代基如前所述，中间体II和III由已知方法制备。以氯仿，二氯甲烷，四氯化碳，正己烷，苯，甲苯，四氢呋喃，二氧六环，丙酮或丁酮为溶剂，上述中间体II和III在碱性条件下如Et3N，吡啶，NaOH，KOH，Na2CO3，K2CO3或NaHCO3存在下或中性条件下，控制反应温度在-40℃～反应液回流温度，30分钟-8小时可生成通式I所表示的化合物。无碱存在下亦可制得目的物。In the above-mentioned intermediates II and III, the substituents are as described above, and the intermediates II and III are prepared by known methods. With chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, tetrahydrofuran, dioxane, acetone or methyl ethyl ketone as solvents, the above intermediates II and III can be used under basic conditions such as Et 3 N, pyridine , NaOH, KOH, Na 2 CO 3 , K 2 CO 3 or NaHCO 3 in the presence or under neutral conditions, control the reaction temperature at -40°C to the reflux temperature of the reaction solution, 30 minutes to 8 hours can generate the formula I compound of. The target product can also be obtained in the absence of alkali.

方法2：Method 2:

Figure A0314337500152
Figure A0314337500152

上述中间体II和IV中，取代基如前所述，中间体II和IV由已知方法制备。以氯仿，二氯甲烷，四氯化碳，正己烷，苯，甲苯，四氢呋喃，二氧六环，丙酮或丁酮为溶剂，上述中间体II和IV在碱性条件下如Et3N，吡啶，NaOH，KOH，Na2CO3，K2CO3或NaHCO3存在下，控制反应温度在-40℃～反应液回流温度，30分钟-8小时可生成通式I所表示的化合物。In the above-mentioned intermediates II and IV, the substituents are as described above, and the intermediates II and IV are prepared by known methods. Using chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, tetrahydrofuran, dioxane, acetone or methyl ethyl ketone as solvents, the above intermediates II and IV are under basic conditions such as Et 3 N, pyridine , in the presence of NaOH, KOH, Na 2 CO 3 , K 2 CO 3 or NaHCO 3 , the reaction temperature is controlled at -40° C. to the reflux temperature of the reaction solution, and the compound represented by general formula I can be generated within 30 minutes to 8 hours.

当-X-选自CH2CH2OCH2CH2，CH2CH2SCH2CH2，CH2CH2N(CH3)CH2CH2，When -X- is selected from CH 2 CH 2 OCH 2 CH 2 , CH 2 CH 2 SCH 2 CH 2 , CH 2 CH 2 N(CH 3 )CH 2 CH 2 ,

CH2CH2，CH2CH2SO2CH2CH2或CH2CH2SOCH2CH2，X1为O，Z等于Q时，CH 2 CH 2 , CH 2 CH 2 SO 2 CH 2 CH 2 or CH 2 CH 2 SOCH 2 CH 2 , X 1 is O, Z is equal to Q,

方法3：Method 3:

中间体II在溶剂如二氯甲烷，四氯化碳，正己烷，苯，甲苯，四氢呋喃，二氧六环，乙酸乙酯、丙酮或丁酮中与中间体V反应，在碱如三乙胺，吡啶，NaOH，KOH，Na2CO3，K2CO3或NaHCO3存在下，控制反应温度在-40℃～反应液回流温度，反应30分钟到8小时得通式I所表示的化合物。无碱存在下亦可制得目的物。Intermediate II reacts with intermediate V in a solvent such as dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, tetrahydrofuran, dioxane, ethyl acetate, acetone or butanone, and reacts with intermediate V in a base such as triethylamine , in the presence of pyridine, NaOH, KOH, Na 2 CO 3 , K 2 CO 3 or NaHCO 3 , controlling the reaction temperature at -40°C to the reflux temperature of the reaction solution, and reacting for 30 minutes to 8 hours to obtain the compound represented by general formula I. The target product can also be obtained in the absence of alkali.

通式I的部分化合物见表1-2。表中，“Pri”表示异丙基，″Ph″表示苯基，″Ph-4-Cl″表示4-氯苯基，″CH2Ph″表示苄基，″CH2Ph-4-Cl″表示4-氯苄基，″PY″表示吡啶基，2-FUR表示2-呋喃基，“MORPHOLINE”表示吗啉基，“4-C6H4-C6H4-4”表示Some compounds of general formula I are shown in Table 1-2. In the table, "Pri" means isopropyl, "Ph" means phenyl, "Ph-4-Cl" means 4-chlorophenyl, "CH 2 Ph" means benzyl, "CH 2 Ph-4-Cl" means 4-chlorobenzyl, "PY" means pyridyl, 2-FUR means 2-furyl, "MORPHOLINE" means morpholinyl, "4-C 6 H 4 -C 6 H 4 -4" means

                    表1 Table 1

No      Q          X-X1-ZNo Q XX 1 -Z

1       Q1         CH2Ph1 Q1 CH 2 Ph

2       Q1         CH2CH2Ph2 Q1 CH 2 CH 2 Ph

3       Q1         CH2CH2Ph-4-Cl3 Q1 CH 2 CH 2 Ph-4-Cl

4       Q1         CH2CH2OPh-4-Cl4 Q1 CH 2 CH 2 OPh-4-Cl

5       Q1         CH2CH2SPh-4-Cl5 Q1 CH 2 CH 2 SPh-4-Cl

6       Q1         CH2CH2SCH2Ph-4-Cl6 Q1 CH 2 CH 2 SCH 2 Ph-4-Cl

7       Q1         CH2COPh-4-Cl7 Q1 CH 2 COPh-4-Cl

8       Q1         CH2COPh-1，4-Cl2 8 Q1 CH 2 COPh-1,4-Cl 2

9       Q1         CH2C(Ph-4-Cl)＝NOCH39 Q1 CH 2 C(Ph-4-Cl)=NOCH3

10      Q1         CH2C(Ph-1，4-Cl2)＝NOCH310 Q1 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

11      Q1         CH2C(Ph-4-Cl)＝NNHCH311 Q1 CH 2 C(Ph-4-Cl)=NNHCH3

12      Q1         CH2C(Ph-1，4-Cl2)＝NNHPh12 Q1 CH 2 C(Ph-1,4-Cl 2 )=NNHPh

13      Q1         N＝C(CH3)Ph-4-Cl13 Q1 N=C(CH 3 )Ph-4-Cl

14      Q1         N＝C(CH2Br)Ph-4-Cl14 Q1 N=C(CH 2 Br)Ph-4-Cl

15      Q1         N＝C(CH2OCH3)Ph-4-Cl15 Q1 N=C(CH 2 OCH 3 )Ph-4-Cl

16      Q1         N＝C(CH2ON＝C(CH3)2)Ph-4-Cl16 Q1 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

17      Q1         N＝C(CO2CH3)Ph-4-Cl17 Q1 N=C(CO 2 CH 3 )Ph-4-Cl

18       Q1        N＝C(CO2CH3)CN18 Q1 N=C(CO 2 CH 3 )CN

19       Q1        N＝C(CO2C2H5)2 19 Q1 N＝C(CO 2 C 2 H 5 ) 2

20       Q1        N＝C(CH3)COCH3 20 Q1 N=C(CH 3 )COCH 3

21       Q1        N＝C(CH3)C(CH3)＝NOCH3 21 Q1 N=C(CH 3 )C(CH 3 )=NOCH 3

22       Q1        N＝C(CH3)C(CH3)＝NOCH2Ph22 Q1 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

23       Q1        N＝C(CH3)C(CH3)＝NOCH2-3-PY-5-Cl23 Q1 N=C(CH 3 )C(CH 3 )=NOCH 2 -3-PY-5-Cl

24       Q1        CH2CON(Pr i)Ph-4-Cl24 Q1 CH 2 CON(Pr i)Ph-4-Cl

25       Q1        CH2CON(Pr i)Ph-4-F25 Q1 CH 2 CON(Pr i)Ph-4-F

26       Q1        CH2CON(CH3)Ph26 Q1 CH 2 CON(CH 3 )Ph

27       Q1        CH2CO-4-MORPHOLINE27 Q1 CH 2 CO-4-MORPHOLINE

28       Q1        CH2CONHCH2CN28 Q1 CH 2 CONHCH 2 CN

29       Q1        CH2CONHCH2CH2CN29 Q1 CH 2 CONH CH 2 CH 2 CN

30       Q1        CH2CONHCH2CO2C2H5 30 Q1 CH 2 CONHCH 2 CO 2 C 2 H 5

31       Q1        CH2CONHCH(CH3)CN31 Q1 CH 2 CONHCH(CH 3 )CN

32       Q1        CH2CONHCH(CH3)(Pr i)CN32 Q1 CH 2 CONHCH(CH 3 )(Pr i)CN

33       Q1        C(CH3)＝CHCOCH3 33 Q1 C(CH 3 )=CHCOCH 3

34       Q1       

Figure A0314337500171
34 Q1
Figure A0314337500171

35       Q2        CH2Ph35 Q2 CH 2 Ph

36       Q2        C(CH3)＝CHCO2C2H5 36 Q2 C(CH 3 )＝CHCO 2 C 2 H 5

37       Q2        CH2CH2Ph-4-Cl 37 Q2CH2CH2Ph -4-Cl

38       Q2        CH2CH2OPh-4-Cl38 Q2CH2CH2OPh - 4-Cl

40       Q2        CH2CH2SPh-4-Cl40 Q2CH2CH2SPh - 4-Cl

41       Q2        CH2COPh-4-Cl41 Q2 CH 2 COPh-4-Cl

42       Q2        CH2C(Ph-1，4-Cl2)＝NOCH342 Q2 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

43       Q2        CH2C(Ph-4-Cl)＝NNHCH343 Q2 CH 2 C(Ph-4-Cl)=NNHCH3

44       Q2        CH2C(Ph-1，4-Cl2)＝NNHPh44 Q2 CH 2 C(Ph-1,4-Cl 2 )=NNHPh

45       Q2        N＝C(CH3)Ph-4-Cl45 Q2 N=C(CH 3 )Ph-4-Cl

46       Q2        N＝C(CH2Br)Ph-4-Cl46 Q2 N=C(CH 2 Br)Ph-4-Cl

47       Q2        N＝C(CH2OCH3)Ph-4-Cl47 Q2 N=C(CH 2 OCH 3 )Ph-4-Cl

48       Q2        N＝C(CH2ON＝C(CH3)2)Ph-4-Cl48 Q2 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

49       Q2        N＝C(CO2CH3)Ph-4-Cl49 Q2 N=C(CO 2 CH 3 )Ph-4-Cl

50       Q2        N＝C(CO2CH3)CN50 Q2 N=C(CO 2 CH 3 )CN

51       Q2        N＝C(CO2C2H5)2 51 Q2 N＝C(CO 2 C 2 H 5 ) 2

52       Q2        N＝C(CH3)COCH3 52 Q2 N=C(CH 3 )COCH 3

53     Q2       N＝C(CH3)C(CH3)＝NOCH3 53 Q2 N=C(CH 3 )C(CH 3 )=NOCH 3

54     Q2       N＝C(CH3)C(CH3)＝NOCH2Ph54 Q2 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

55     Q2       N＝C(CH3)C(CH3)＝NOCH2-3-PY-5-Cl55 Q2 N=C(CH 3 )C(CH 3 )=NOCH 2 -3-PY-5-Cl

56     Q2       CH2CON(Pr i)Ph-4-Cl56 Q2 CH 2 CON(Pr i)Ph-4-Cl

57     Q2       CH2CON(Pr i)Ph-4-F57 Q2 CH 2 CON(Pr i)Ph-4-F

58     Q2       CH2CONHPh58 Q2 CH 2 CONHPh

59     Q2       CH2CONH-2-PY59 Q2 CH 2 CONH-2-PY

60     Q2       CH2CONHCH2CN60 Q2 CH 2 CONHCH 2 CN

61     Q2       CH2CONHCH2CH2CN61 Q2 CH 2 CONHCH 2 CH 2 CN

62     Q2       CH2CONHCH2CO2C2H5 62 Q2 CH 2 CONHCH 2 CO 2 C 2 H 5

63     Q2       CH2CONHCH(CH3)CN63 Q2 CH 2 CONHCH(CH 3 )CN

64     Q2       CH2CONHCH(CH3)(Pr i)CN64 Q2 CH 2 CONHCH(CH 3 )(Pr i)CN

65     Q2       C(CH3)＝CHCOCH3 65 Q2 C(CH 3 )＝CHCOCH 3

66     Q2       66 Q2

67     Q3       CH2Ph67 Q3 CH 2 Ph

68     Q3       CH2CH2Ph68 Q3 CH 2 CH 2 Ph

69     Q3       CH2CH2Ph-4-Cl 69 Q3CH2CH2Ph -4-Cl

70     Q3       CH2CH2OPh-4-Cl70 Q3CH2CH2OPh - 4-Cl

71     Q3       CH2CH2SPh-4-Cl71 Q3 CH 2 CH 2 SPh-4-Cl

72     Q3       CH2COPh-4-Cl72 Q3 CH 2 COPh-4-Cl

73     Q3       CH2C(Ph-1，4-Cl2)＝NOCH373 Q3 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

74     Q3       CH2C(Ph-4-Cl)＝NNHCH374 Q3 CH 2 C(Ph-4-Cl)=NNHCH3

75     Q3       CH2C(Ph-1，4-Cl2)＝NNHPh75 Q3 CH 2 C(Ph-1,4-Cl 2 )=NNHPh

76     Q3       N＝C(CH3)Ph-4-Cl76 Q3 N=C(CH 3 )Ph-4-Cl

77     Q3       N＝C(CH2Br)Ph-4-Cl77 Q3 N=C(CH 2 Br)Ph-4-Cl

78     Q3       N＝C(CH2OCH3)Ph-4-Cl78 Q3 N=C(CH 2 OCH 3 )Ph-4-Cl

79     Q3       N＝C(CH2ON＝C(CH3)2)Ph-4-Cl79 Q3 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

80     Q3       N＝C(CO2CH3)Ph-4-Cl80 Q3 N=C(CO 2 CH 3 )Ph-4-Cl

81     Q3       N＝C(CO2CH3)CN81 Q3 N=C(CO 2 CH 3 )CN

82     Q3       N＝C(CO2C2H5)2 82 Q3 N＝C(CO 2 C 2 H 5 ) 2

83     Q3       N＝C(CH3)COCH3 83 Q3 N=C(CH 3 )COCH 3

84     Q3       N＝C(CH3)C(CH3)＝NOCH3 84 Q3 N=C(CH 3 )C(CH 3 )=NOCH 3

85     Q3       N＝C(CH3)C(CH3)＝NOCH2Ph85 Q3 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

86     Q3       N＝C(CH3)C(CH3)＝NOCH2-3-PY-5-Cl86 Q3 N=C(CH 3 )C(CH 3 )=NOCH 2 -3-PY-5-Cl

87       Q3       CH2CON(Pr i)Ph-4-Cl87 Q3 CH 2 CON(Pr i)Ph-4-Cl

88       Q3       CH2CON(CH3)2 88 Q3 CH 2 CON(CH 3 ) 2

89       Q3       CH2CONHPh89 Q3 CH 2 CONHPh

90       Q3       CH2CONH-2-PY90 Q3 CH 2 CONH-2-PY

91       Q3       CH2CONHCH2CN91 Q3 CH 2 CONHCH 2 CN

92       Q3       CH2CONHCH2 CH2CN92 Q3 CH 2 CONHCH 2 CH 2 CN

93       Q3       CH2CONHCH2CO2C2H5 93 Q3 CH 2 CONHCH 2 CO 2 C 2 H 5

94       Q3       CH2CONHCH(CH3)CN94 Q3 CH 2 CONHCH(CH 3 )CN

95       Q3       CH2CONHCH(CH3)(Pr i)CN95 Q3 CH 2 CONHCH(CH 3 )(Pr i)CN

96       Q3       C(CH3)＝CHCOCH3 96 Q3 C(CH 3 )=CHCOCH 3

97       Q3       C(CH3)＝CHCO2C2H5 97 Q3 C(CH 3 )＝CHCO 2 C 2 H 5

98       Q4       CH2Ph98 Q4 CH 2 Ph

99       Q4       CH2CH2Ph99 Q4 CH 2 CH 2 Ph

100      Q4       CH2CH2Ph-4-Cl100 Q4CH2CH2Ph - 4-Cl

101      Q4       CH2CH2OPh-4-Cl101 Q4CH2CH2OPh - 4-Cl

102      Q4       CH2CH2SPh-4-Cl102 Q4CH2CH2SPh - 4-Cl

103      Q4       CH2COPh-4-Cl103 Q4 CH 2 COPh-4-Cl

104      Q4       CH2C(Ph-1，4-Cl2)＝NOCH3104 Q4 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

105      Q4       CH2C(Ph-4-Cl)＝NNHCH3105 Q4 CH 2 C(Ph-4-Cl)＝NNHCH3

106      Q4       CH2C(Ph-1，4-Cl2)＝NNHPh106 Q4 CH 2 C(Ph-1,4-Cl 2 )=NNHPh

107      Q4       N＝C(CH3)Ph-4-Cl107 Q4 N=C(CH 3 )Ph-4-Cl

108      Q4       N＝C(CH2Br)Ph-4-Cl108 Q4 N=C(CH 2 Br)Ph-4-Cl

109      Q4       N＝C(CH2OCH3)Ph-4-Cl109 Q4 N=C(CH 2 OCH 3 )Ph-4-Cl

110      Q4       N＝C(CH2ON＝C(CH3)2)Ph-4-Cl110 Q4 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

111      Q4       N＝C(CO2CH3)Ph-4-Cl111 Q4 N=C(CO 2 CH 3 )Ph-4-Cl

112      Q4       N＝C(CO2CH3)CN112 Q4 N=C(CO 2 CH 3 )CN

113      Q4       N＝C(CO2C2H5)2 113 Q4 N＝C(CO 2 C 2 H 5 ) 2

114      Q4       N＝C(CH3)COCH3 114 Q4 N=C(CH 3 )COCH 3

115      Q4       N＝C(CH3)C(CH3)＝NOCH3 115 Q4 N=C(CH 3 )C(CH 3 )=NOCH 3

116      Q4       N＝C(CH3)C(CH3)＝NOCH2Ph116 Q4 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

117      Q4       N＝C(CH3)C(CH3)＝NOCH2-3-PY-5-Cl117 Q4 N=C(CH 3 )C(CH 3 )=NOCH 2 -3-PY-5-Cl

118      Q4       CH2CON(Pri)Ph-4-Cl118 Q4 CH 2 CON(Pri)Ph-4-Cl

119      Q4       CH2CON(Pri)Ph-4-F119 Q4 CH 2 CON(Pri)Ph-4-F

120      Q4       CH2CONHPh120 Q4 CH 2 CONHPh

121      Q4       CH2CONH-2-PY121 Q4 CH 2 CONH-2-PY

122       Q4        CH2CONHCH2CN122 Q4 CH 2 CONHCH 2 CN

123       Q4        CH2CONHCH2CH2CN123 Q4 CH 2 CONH CH 2 CH 2 CN

124       Q4        CH2CONHCH2CO2C2H5 124 Q4 CH 2 CONHCH 2 CO 2 C 2 H 5

125       Q4        CH2CONHCH(CH3)CN125 Q4 CH 2 CONHCH(CH 3 )CN

126       Q4        CH2CONHCH(CH3)(Pr i)CN126 Q4 CH 2 CONHCH(CH 3 )(Pr i)CN

127       Q4        C(CH3)＝CHCOCH3 127 Q4 C(CH 3 )＝CHCOCH 3

128       Q4        C(CH3)＝CHCO2C2H5 128 Q4 C(CH 3 )＝CHCO 2 C 2 H 5

129       Q5        CH2Ph129 Q5 CH 2 Ph

130       Q5        CH2CH2Ph130 Q5 CH 2 CH 2 Ph

131       Q5        CH2CH2Ph-4-Cl 131 Q5CH2CH2Ph -4-Cl

132       Q5        CH2CH2OPh-4-Cl 132 Q5CH2CH2OPh -4-Cl

133       Q5        CH2CH2SPh-4-Cl133 Q5 CH 2 CH 2 SPh-4-Cl

134       Q5        CH2COPh-4-Cl134 Q5 CH 2 COPh-4-Cl

135       Q5        CH2C(Ph-1，4-Cl2)＝NOCH3135 Q5 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

136       Q5        CH2C(Ph-4-Cl)＝NNHCH3136 Q5 CH 2 C(Ph-4-Cl)=NNHCH3

137       Q5        CH2C(Ph-1，4-Cl2)＝NNHPh137 Q5 CH 2 C(Ph-1,4-Cl 2 )=NNHPh

138       Q5        N＝C(CH3)Ph-4-Cl138 Q5 N=C(CH 3 )Ph-4-Cl

139       Q5        N＝C(CH2Br)Ph-4-Cl139 Q5 N=C(CH 2 Br)Ph-4-Cl

140       Q5        N＝C(CH2OCH3)Ph-4-Cl140 Q5 N=C(CH 2 OCH 3 )Ph-4-Cl

141       Q5        N＝C(CH2ON＝C(CH3)2)Ph-4-Cl141 Q5 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

142       Q5        N＝C(CO2CH3)Ph-4-Cl142 Q5 N=C(CO 2 CH 3 )Ph-4-Cl

143       Q5        N＝C(CO2CH3)CN143 Q5 N=C(CO 2 CH 3 )CN

144       Q5        N＝C(CO2C2H5)2 144 Q5 N＝C(CO 2 C 2 H 5 ) 2

145       Q5        N＝C(CH3)COCH3 145 Q5 N=C(CH 3 )COCH 3

146       Q5        N＝C(CH3)C(CH3)＝NOCH3 146 Q5 N=C(CH 3 )C(CH 3 )=NOCH 3

147       Q5        N＝C(CH3)C(CH3)＝NOCH2Ph147 Q5 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

148       Q5        N＝C(CH3)C(CH3)＝NOCH2-3-PY-5-Cl148 Q5 N=C(CH 3 )C(CH 3 )=NOCH 2 -3-PY-5-Cl

149       Q5        CH2CON(Pr i)Ph-4-Cl149 Q5 CH 2 CON(Pr i)Ph-4-Cl

150       Q5        CH2CON(Pr i)CH2Ph-4-F150 Q5 CH 2 CON(Pr i)CH 2 Ph-4-F

151       Q5        CH2CONHPh151 Q5 CH 2 CONHPh

152       Q5        CH2CONH-2-PY152 Q5 CH 2 CONH-2-PY

153       Q5        CH2CONHCH2CN153 Q5 CH 2 CONHCH 2 CN

154       Q5        CH2CONHCH2CH2CN154 Q5 CH 2 CONH CH 2 CH 2 CN

155       Q5        CH2CONHCH2CO2C2H5 155 Q5 CH 2 CONHCH 2 CO 2 C 2 H 5

156       Q5        CH2CONHCH(CH3)CN156 Q5 CH 2 CONHCH(CH 3 )CN

157      Q5           CH2CONHCH(CH3)(Pr i)CN157 Q5 CH 2 CONHCH(CH 3 )(Pr i)CN

158      Q5           C(CH3)＝CHCOCH3 158 Q5 C(CH 3 )＝CHCOCH 3

159      Q5           C(CH3)＝CHCO2C2H5 159 Q5 C(CH 3 )＝CHCO 2 C 2 H 5

160      Q6           CH2Ph160 Q6 CH 2 Ph

161      Q6           CH2CH2Ph161 Q6 CH 2 CH 2 Ph

162      Q6           CH2CH2Ph-4-Cl 162 Q6CH2CH2Ph -4-Cl

163      Q6           CH2CH2OPh-4-Cl163 Q6 CH 2 CH 2 OPh-4-Cl

164      Q6           CH2CH2SPh-4-Cl164 Q6 CH 2 CH 2 SPh-4-Cl

165      Q6           CH2COPh-4-Cl165 Q6 CH 2 COPh-4-Cl

166      Q6           CH2C(Ph-1，4-Cl2)＝NOCH3166 Q6 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

167      Q6           CH2C(Ph-4-Cl)＝NNHCH3167 Q6 CH 2 C(Ph-4-Cl)=NNHCH3

168      Q6           CH2C(Ph-1，4-Cl2)＝NNHPh168 Q6 CH 2 C(Ph-1,4-Cl 2 )=NNHPh

169      Q6           N＝C(CH3)Ph-4-Cl169 Q6 N=C(CH 3 )Ph-4-Cl

170      Q6           N＝C(CH2Br)Ph-4-Cl170 Q6 N=C(CH 2 Br)Ph-4-Cl

171      Q6           N＝C(CH2OCH3)Ph-4-Cl171 Q6 N=C(CH 2 OCH 3 )Ph-4-Cl

172      Q6           N＝C(CH2ON＝C(CH3)2)Ph-4-Cl172 Q6 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

173      Q6           N＝C(CO2CH3)Ph-4-Cl173 Q6 N=C(CO 2 CH 3 )Ph-4-Cl

174      Q6           N＝C(CO2CH3)CN174 Q6 N=C(CO 2 CH 3 )CN

175      Q6           N＝C(CO2C2H5)2 175 Q6 N＝C(CO 2 C 2 H 5 ) 2

176      Q6           N＝C(CH3)COCH3 176 Q6 N=C(CH 3 )COCH 3

177      Q6           N＝C(CH3)C(CH3)＝NOCH3 177 Q6 N=C(CH 3 )C(CH 3 )=NOCH 3

178      Q6           N＝C(CH3)C(CH3)＝NOCH2Ph178 Q6 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

179      Q6           N＝C(CH3)C(CH3)＝NOCH2-3-PY-5-Cl179 Q6 N=C(CH 3 )C(CH 3 )=NOCH 2 -3-PY-5-Cl

180      Q6           CH2CON(Pr i)Ph-4-Cl180 Q6 CH 2 CON(Pr i)Ph-4-Cl

181      Q6           CH2CON(Pr i)Ph-4-F181 Q6 CH 2 CON(Pr i)Ph-4-F

182      Q6           CH2CONHPh182 Q6 CH 2 CONHPh

183      Q6           CH2CONH-2-PY183 Q6 CH 2 CONH-2-PY

184      Q6           CH2CONHCH2CN184 Q6 CH 2 CONHCH 2 CN

185      Q6           CH2CONHCH2CH2CN185 Q6 CH 2 CONH CH 2 CH 2 CN

186      Q6           CH2CONHCH2CO2C2H5 186 Q6 CH 2 CONHCH 2 CO 2 C 2 H 5

187      Q6           CH2CONHCH(CH3)CN187 Q6 CH 2 CONHCH(CH 3 )CN

188      Q6           CH2CONHCH(CH3)(Pr i)CN188 Q6 CH 2 CONHCH(CH 3 )(Pr i)CN

189      Q6           C(CH3)＝CHCOCH3 189 Q6 C(CH 3 )＝CHCOCH 3

190      Q6           C(CH3)＝CHCO2C2H5 190 Q6 C(CH 3 )＝CHCO 2 C 2 H 5

191      Q7           CH2Ph191 Q7 CH 2 Ph

192      Q7           CH2CH2Ph192 Q7 CH 2 CH 2 Ph

193      Q7           CH2CH2Ph-4-Cl 193 Q7CH2CH2Ph -4-Cl

194      Q7           CH2CH2OPh-4-Cl194 Q7CH2CH2OPh - 4-Cl

195      Q7           CH2CH2SPh-4-Cl 195 Q7CH2CH2SPh -4-Cl

196      Q7           CH2COPh-4-Cl196 Q7 CH 2 COPh-4-Cl

197      Q7           CH2C(Ph-1，4-Cl2)＝NOCH3197 Q7 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

198      Q7           CH2C(Ph-4-Cl)＝NNHCH3198 Q7 CH 2 C(Ph-4-Cl)=NNHCH3

199      Q7           CH2C(Ph-1，4-Cl2)＝NNHPh199 Q7 CH 2 C(Ph-1,4-Cl 2 )=NNHPh

200      Q7           N＝C(CH3)Ph-4-Cl200 Q7 N=C(CH 3 )Ph-4-Cl

201      Q7           N＝C(CH2Br)Ph-4-Cl201 Q7 N=C(CH 2 Br)Ph-4-Cl

202      Q7           N＝C(CH2OCH3)Ph-4-Cl202 Q7 N=C(CH 2 OCH 3 )Ph-4-Cl

203      Q7           N＝C(CH2ON＝C(CH3)2)Ph-4-Cl203 Q7 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

204      Q7           N＝C(CO2CH3)Ph-4-Cl204 Q7 N=C(CO 2 CH 3 )Ph-4-Cl

205      Q7           N＝C(CO2CH3)CN205 Q7 N=C(CO 2 CH 3 )CN

206      Q7           N＝C(CO2C2H5)2 206 Q7 N＝C(CO 2 C 2 H 5 ) 2

207      Q7           N＝C(CH3)COCH3 207 Q7 N=C(CH 3 )COCH 3

208      Q7           N＝C(CH3)C(CH3)＝NOCH3 208 Q7 N=C(CH 3 )C(CH 3 )=NOCH 3

209      Q7           N＝C(CH3)C(CH3)＝NOCH2Ph209 Q7 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

210      Q7           N＝C(CH3)C(CH3)＝NOCH2-3-PY-5-Cl210 Q7 N=C(CH 3 )C(CH 3 )=NOCH 2 -3-PY-5-Cl

211      Q7           CH2CON(Pr i)Ph-4-Cl211 Q7 CH 2 CON(Pr i)Ph-4-Cl

212      Q7           CH2CON(Pr i)Ph-4-F212 Q7 CH 2 CON(Pr i)Ph-4-F

213      Q7           CH2CONHPh213 Q7 CH 2 CONHPh

214      Q7           CH2CONH-2-PY214 Q7 CH 2 CONH-2-PY

215      Q7           CH2CONHCH2CN215 Q7 CH 2 CONHCH 2 CN

216      Q7           CH2CONHCH2 CH2CN216 Q7 CH 2 CONH CH 2 CH 2 CN

217      Q7           CH2CONHCH2CO2C2H5 217 Q7 CH 2 CONHCH 2 CO 2 C 2 H 5

218      Q7           CH2CONHCH(CH3)CN218 Q7 CH 2 CONHCH(CH 3 )CN

219      Q7           CH2CONHCH(CH3)(Pri)CN219 Q7 CH 2 CONHCH(CH 3 )(Pri)CN

220      Q7           C(CH3)＝CHCOCH3 220 Q7 C(CH 3 )＝CHCOCH 3

221      Q7           C(CH3)＝CHCO2C2H5 221 Q7 C(CH 3 )＝CHCO 2 C 2 H 5

222      Q8           CH2Ph222 Q8 CH 2 Ph

223      Q8           CH2CH2Ph-4-Cl 223 Q8CH2CH2Ph -4-Cl

224      Q8           CH2CH2OPh-4-Cl224 Q8 CH 2 CH 2 OPh-4-Cl

225      Q8           CH2COPh-4-Cl225 Q8 CH 2 COPh-4-Cl

226      Q8           CH2C(Ph-1，4-Cl2)＝NOCH3226 Q8 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

227      Q8           CH2C(Ph-4-Cl)＝NNHCH3227 Q8 CH 2 C(Ph-4-Cl)=NNHCH3

228      Q8           N＝C(CH3)Ph-4-Cl228 Q8 N=C(CH 3 )Ph-4-Cl

229      Q8           N＝C(CH2OCH3)Ph-4-Cl229 Q8 N=C(CH 2 OCH 3 )Ph-4-Cl

230      Q8           N＝C(CH2ON＝C(CH3)2)Ph-4-Cl230 Q8 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

231      Q8           N＝C(CO2CH3)Ph-4-Cl231 Q8 N=C(CO 2 CH 3 )Ph-4-Cl

232      Q8           N＝C(CO2CH3)CN232 Q8 N=C(CO 2 CH 3 )CN

233      Q8           N＝C(CO2C2H5)2 233 Q8 N＝C(CO 2 C 2 H 5 ) 2

234      Q8           N＝C(CH3)COCH3 234 Q8 N=C(CH 3 )COCH 3

235      Q8           N＝C(CH3)C(CH3)＝NOCH2Ph235 Q8 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

236      Q8           CH2CON(Pr i)Ph-4-Cl236 Q8 CH 2 CON(Pr i)Ph-4-Cl

237      Q8           CH2CONHPh237 Q8 CH 2 CONHPh

238      Q8           CH2CONH-2-PY238 Q8 CH 2 CONH-2-PY

239      Q8           CH2CONHCH2CN239 Q8 CH 2 CONHCH 2 CN

240      Q8           CH2CONHCH2 CH2CN240 Q8 CH 2 CONHCH 2 CH 2 CN

241      Q8           CH2CONHCH2CO2C2H5 241 Q8 CH 2 CONH CH 2 CO 2 C 2 H 5

242      Q8           CH2CONHCH(CH3)(Pr i)CN242 Q8 CH 2 CONHCH(CH 3 )(Pr i)CN

243      Q8           C(CH3)＝CHCOCH3 243 Q8 C(CH 3 )＝CHCOCH 3

244      Q8           C(CH3)＝CHCO2C2H5 244 Q8 C(CH 3 )＝CHCO 2 C 2 H 5

245      Q9           CH2Ph245 Q9 CH 2 Ph

246      Q9           CH2CH2Ph-4-Cl 246 Q9CH2CH2Ph -4-Cl

247      Q9           CH2CH2OPh-4-Cl247 Q9CH2CH2OPh - 4-Cl

248      Q9           CH2COPh-4-Cl248 Q9 CH 2 COPh-4-Cl

249      Q9           CH2C(Ph-1，4-Cl2)＝NOCH3249 Q9 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

250      Q9           CH2C(Ph-4-Cl)＝NNHCH3250 Q9 CH 2 C(Ph-4-Cl)＝NNHCH3

251      Q9           N＝C(CH3)Ph-4-Cl251 Q9 N=C(CH 3 )Ph-4-Cl

252      Q9           N＝C(CH2OCH3)Ph-4-Cl252 Q9 N=C(CH 2 OCH 3 )Ph-4-Cl

253      Q9           N＝C(CH2ON＝C(CH3)2)Ph-4-Cl253 Q9 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

254      Q9           N＝C(CO2CH3)Ph-4-Cl254 Q9 N=C(CO 2 CH 3 )Ph-4-Cl

255      Q9           N＝C(CO2CH3)CN255 Q9 N=C(CO 2 CH 3 )CN

256      Q9           N＝C(CO2C2H5)2 256 Q9 N＝C(CO 2 C 2 H 5 ) 2

257      Q9           N＝C(CH3)COCH3 257 Q9 N=C(CH 3 )COCH 3

258      Q9           N＝C(CH3)C(CH3)＝NOCH2Ph258 Q9 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

259      Q9           CH2CON(Pr i)Ph-4-Cl259 Q9 CH 2 CON(Pr i)Ph-4-Cl

260      Q9           CH2CONHPh260 Q9 CH 2 CONHPh

261      Q9           CH2CONH-2-PY261 Q9 CH 2 CONH-2-PY

262      Q9          CH2CONHCH2CN262 Q9 CH 2 CONHCH 2 CN

263      Q9          CH2CONHCH2CH2CN263 Q9 CH 2 CON H CH 2 CH 2 CN

264      Q9          CH2CONHCH2CO2C2H5 264 Q9 CH 2 CONH CH 2 CO 2 C 2 H 5

265      Q9          CH2CONHCH(CH3)(Pr i)CN265 Q9 CH 2 CONHCH(CH 3 )(Pr i)CN

266      Q9          C(CH3)＝CHCOCH3 266 Q9 C(CH 3 )＝CHCOCH 3

267      Q9          C(CH3)＝CHCO2C2H5 267 Q9 C(CH 3 )＝CHCO 2 C 2 H 5

268      Q10         CH2Ph268 Q10 CH 2 Ph

269      Q10         CH2CH2Ph-4-Cl269 Q10CH2CH2Ph - 4-Cl

270      Q10         CH2CH2OPh-4-Cl270 Q10CH2CH2OPh - 4-Cl

271      Q10         CH2COPh-4-Cl271 Q10 CH 2 COPh-4-Cl

272      Q10         CH2C(Ph-1，4-Cl2)＝NOCH3272 Q10 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

273      Q10         CH2C(Ph-4-Cl)＝NNHCH3273 Q10 CH 2 C(Ph-4-Cl)＝NNHCH3

274      Q10         N＝C(CH3)Ph-4-Cl274 Q10 N=C(CH 3 )Ph-4-Cl

275      Q10         N＝C(CH2OCH3)Ph-4-Cl275 Q10 N=C(CH 2 OCH 3 )Ph-4-Cl

276      Q10         N＝C(CH2ON＝C(CH3)2)Ph-4-Cl276 Q10 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

277      Q10         N＝C(CO2CH3)Ph-4-Cl277 Q10 N=C(CO 2 CH 3 )Ph-4-Cl

278      Q10         N＝C(CO2CH3)CN278 Q10 N=C(CO 2 CH 3 )CN

279      Q10         N＝C(CO2C2H5)2 279 Q10 N＝C(CO 2 C 2 H 5 ) 2

280      Q10         N＝C(CH3)COCH3 280 Q10 N=C(CH 3 )COCH 3

281      Q10         N＝C(CH3)C(CH3)＝NOCH2Ph281 Q10 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

282      Q10         CH2CON(Pr i)Ph-4-Cl282 Q10 CH 2 CON(Pr i)Ph-4-Cl

283      Q10         CH2CONHPh283 Q10 CH 2 CONHPh

284      Q10         CH2CONH-2-PY284 Q10 CH 2 CONH-2-PY

285      Q10         CH2CONHCH2CN285 Q10 CH 2 CONHCH 2 CN

286      Q10         CH2CONHCH2CH2CN286 Q10 CH 2 CON H CH 2 CH 2 CN

287      Q10         CH2CONHCH2CO2C2H5 287 Q10 CH 2 CONH CH 2 CO 2 C 2 H 5

288      Q10         CH2CONHCH(CH3)(Pr i)CN288 Q10 CH 2 CONHCH(CH 3 )(Pr i)CN

289      Q10         C(CH3)＝CHCOCH3 289 Q10 C(CH 3 )＝CHCOCH 3

290      Q10         C(CH3)＝CHCO2C2H5 290 Q10 C(CH 3 )＝CHCO 2 C 2 H 5

291      Q11         CH2Ph291 Q11 CH 2 Ph

292      Q11         CH2CH2Ph-4-Cl292 Q11CH2CH2Ph - 4-Cl

293      Q11         CH2CH2OPh-4-Cl293 Q11CH2CH2OPh - 4-Cl

294      Q11         CH2COPh-4-Cl294 Q11 CH 2 COPh-4-Cl

295      Q11         CH2C(Ph-1，4-Cl2)＝NOCH3295 Q11 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

296      Q11         CH2C(Ph-4-Cl)＝NNHCH3296 Q11 CH 2 C(Ph-4-Cl)=NNHCH3

297      Q11        N＝C(CH3)Ph-4-Cl297 Q11 N=C(CH 3 )Ph-4-Cl

298      Q11        N＝C(CH2OCH3)Ph-4-Cl298 Q11 N=C(CH 2 OCH 3 )Ph-4-Cl

299      Q11        N＝C(CH2ON＝C(CH3)2)Ph-4-Cl299 Q11 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

300      Q11        N＝C(CO2CH3)Ph-4-Cl300 Q11 N=C(CO 2 CH 3 )Ph-4-Cl

301      Q11        N＝C(CO2CH3)CN301 Q11 N=C(CO 2 CH 3 )CN

302      Q11        N＝C(CO2C2H5)2 302 Q11 N＝C(CO 2 C 2 H 5 ) 2

303      Q11        N＝C(CH3)COCH3 303 Q11 N=C(CH 3 )COCH 3

304      Q11        N＝C(CH3)C(CH3)＝NOCH2Ph304 Q11 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

305      Q11        CH2CON(Pr i)Ph-4-Cl305 Q11 CH 2 CON(Pr i)Ph-4-Cl

306      Q11        CH2CONHPh306 Q11 CH 2 CONHPh

307      Q11        CH2CONH-2-PY307 Q11 CH 2 CONH-2-PY

308      Q11        CH2CONHCH2CN308 Q11 CH 2 CONHCH 2 CN

309      Q11        CH2CONHCH2 CH2CN309 Q11 CH 2 CONH CH 2 CH 2 CN

310      Q11        CH2CONHCH2CO2C2H5 310 Q11 CH 2 CONHCH 2 CO 2 C 2 H 5

311      Q11        CH2CONHCH(CH3)(Pri)CN311 Q11 CH 2 CONHCH(CH 3 )(Pri)CN

312      Q11        C(CH3)＝CHCOCH3 312 Q11 C(CH 3 )=CHCOCH 3

313      Q11        C(CH3)＝CHCO2C2H5 313 Q11 C(CH 3 )＝CHCO 2 C 2 H 5

314      Q12        CH2Ph314 Q12 CH 2 Ph

315      Q12        CH2CH2Ph-4-Cl315 Q12CH2CH2Ph - 4-Cl

316      Q12        CH2CH2OPh-4-Cl316 Q12CH2CH2OPh - 4-Cl

317      Q12        CH2COPh-4-Cl317 Q12 CH 2 COPh-4-Cl

318      Q12        CH2C(Ph-1，4-Cl2)＝NOCH3318 Q12 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

319      Q12        CH2C(Ph-4-Cl)＝NNHCH3319 Q12 CH 2 C(Ph-4-Cl)=NNHCH3

320      Q12        N＝C(CH3)Ph-4-Cl320 Q12 N=C(CH 3 )Ph-4-Cl

321      Q12        N＝C(CH2OCH3)Ph-4-Cl321 Q12 N=C(CH 2 OCH 3 )Ph-4-Cl

322      Q12        N＝C(CH2ON＝C(CH3)2)Ph-4-Cl322 Q12 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

323      Q12        N＝C(CO2CH3)Ph-4-Cl323 Q12 N=C(CO 2 CH 3 )Ph-4-Cl

324      Q12        N＝C(CO2CH3)CN324 Q12 N=C(CO 2 CH 3 )CN

325      Q12        N＝C(CO2C2H5)2 325 Q12 N＝C(CO 2 C 2 H 5 ) 2

326      Q12        N＝C(CH3)COCH3 326 Q12 N=C(CH 3 )COCH 3

327      Q12        N＝C(CH3)C(CH3)＝NOCH2Ph327 Q12 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

328      Q12        CH2CON(Pr i)Ph-4-Cl328 Q12 CH 2 CON(Pr i)Ph-4-Cl

329      Q12        CH2CONHPh329 Q12 CH 2 CONHPh

330      Q12        CH2CONH-2-PY330 Q12 CH 2 CONH-2-PY

331      Q12        CH2CONHCH2CN331 Q12 CH 2 CONHCH 2 CN

332     Q12            CH2CONHCH2CH2CN332 Q12 CH 2 CONHCH 2 CH 2 CN

333     Q12            CH2CONHCH2CO2C2H5 333 Q12 CH 2 CONHCH 2 CO 2 C 2 H 5

334     Q12            CH2CONHCH(CH3)(Pr i)CN334 Q12 CH 2 CONHCH(CH 3 )(Pr i)CN

335     Q12            C(CH3)＝CHCOCH3 335 Q12 C(CH 3 )=CHCOCH 3

336     Q12            C(CH3)＝CHCO2C2H5 336 Q12 C(CH 3 )＝CHCO 2 C 2 H 5

337     Q13            CH2Ph337 Q13 CH 2 Ph

338     Q13            CH2CH2Ph-4-Cl338 Q13CH2CH2Ph - 4-Cl

339     Q13            CH2CH2OPh-4-Cl339 Q13CH2CH2OPh - 4-Cl

340     Q13            CH2COPh-4-Cl340 Q13 CH 2 COPh-4-Cl

341     Q13            CH2C(Ph-1，4-Cl2)＝NOCH3341 Q13 CH 2 C(Ph-1,4-Cl 2 )=NOCH3

342     Q13            CH2C(Ph-4-Cl)＝NNHCH3342 Q13 CH 2 C(Ph-4-Cl)=NNHCH3

343     Q13            N＝C(CH3)Ph-4-Cl343 Q13 N=C(CH 3 )Ph-4-Cl

344     Q13            N＝C(CH2OCH3)Ph-4-Cl344 Q13 N=C(CH 2 OCH 3 )Ph-4-Cl

345     Q13            N＝C(CH2ON＝C(CH3)2)Ph-4-Cl345 Q13 N=C(CH 2 ON=C(CH 3 ) 2 )Ph-4-Cl

346     Q13            N＝C(CO2CH3)Ph-4-Cl346 Q13 N=C(CO 2 CH 3 )Ph-4-Cl

347     Q13            N＝C(CO2CH3)CN347 Q13 N=C(CO 2 CH 3 )CN

348     Q13            N＝C(CO2C2H5)2 348 Q13 N＝C(CO 2 C 2 H 5 ) 2

349     Q13            N＝C(CH3)COCH3 349 Q13 N=C(CH 3 )COCH 3

350     Q13            N＝C(CH3)C(CH3)＝NOCH2Ph350 Q13 N=C(CH 3 )C(CH 3 )=NOCH 2 Ph

351     Q13            CH2CON(Pr i)Ph-4-Cl351 Q13 CH 2 CON(Pr i)Ph-4-Cl

352     Q13            CH2CONHPh352 Q13 CH 2 CONHPh

353     Q13            CH2CONH-2-PY353 Q13 CH 2 CONH-2-PY

354     Q13            CH2CONHCH2CN354 Q13 CH 2 CONHCH 2 CN

355     Q13            CH2CONHCH2CH2CN355 Q13 CH 2 CON H CH 2 CH 2 CN

356     Q13            CH2CONHCH2CO2C2H5 356 Q13 CH 2 CONHCH 2 CO 2 C 2 H 5

357     Q13            CH2CONHCH(CH3)(Pr i)CN357 Q13 CH 2 CONHCH(CH 3 )(Pr i)CN

358     Q13            C(CH3)＝CHCOCH3 358 Q13 C(CH 3 )＝CHCOCH 3

359     Q13            C(CH3)＝CHCO2C2H5 359 Q13 C(CH 3 )＝CHCO 2 C 2 H 5

                          表2 Table 2

                         X1＝OX 1 =O

No      Q             X                         ZNo Q X X Z

360     Q1     CH2CH2OCH2CH2               Q1360 Q1 CH 2 CH 2 OCH 2 CH 2 Q1

361     Q1     CH2CH2SCH2CH2               Q1361 Q1 CH 2 CH 2 SCH 2 CH 2 Q1

362     Q1     CH2CH2                         Q1362 Q1 CH 2 CH 2 Q1

363     Q1     CH2CH2SO2CH2CH2            Q1 363 Q1 CH2CH2SO2CH2CH2Q1 _ _

364     Q1     CH2CH2N(CH3)CH2CH2         Q1364 Q1 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q1

365     Q1     N＝C(CH3)C(CH3)＝N             Q1365 Q1 N=C(CH 3 )C(CH 3 )=N Q1

366     Q1     1，2-C6H4                      Q1366 Q1 1, 2-C 6 H 4 Q1

367     Q1     1，4-C6H4                      Q1367 Q1 1, 4-C 6 H 4 Q1

368     Q1     1，3-C6H4                      Q1368 Q1 1, 3-C 6 H 4 Q1

369     Q1     4-C6H4-4-C6H4-4             Q1369 Q1 4-C 6 H 4 -4-C 6 H 4 -4 Q1

370     Q2     CH2CH2OCH2CH2               Q2370 Q2 CH 2 CH 2 OCH 2 CH 2 Q2

371     Q2     CH2CH2SCH2CH2               Q2371 Q2 CH 2 CH 2 SCH 2 CH 2 Q2

372     Q2     CH2CH2、                       Q2372 Q2 CH 2 CH 2 、 Q2

373     Q2     CH2CH2SO2CH2CH2            Q2373 Q2 CH 2 CH 2 SO 2 CH 2 CH 2 Q2

374     Q2     CH2CH2N(CH3)CH2CH2         Q2374 Q2 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q2

375     Q2     N＝C(CH3)C(CH3)＝N             Q2375 Q2 N=C(CH 3 )C(CH 3 )=N Q2

376     Q2     1，2-C6H4                      Q2376 Q2 1, 2-C 6 H 4 Q2

377     Q2     1，4-C6H4                      Q2377 Q2 1, 4-C 6 H 4 Q2

378     Q2     1，3-C6H4                      Q2378 Q2 1, 3-C 6 H 4 Q2

379     Q2     4-C6H4-4-C6H4-4             Q2379 Q2 4-C 6 H 4 -4-C 6 H 4 -4 Q2

380     Q3     CH2CH2OCH2CH2               Q3380 Q3 CH 2 CH 2 OCH 2 CH 2 Q3

381     Q3     CH2CH2SCH2CH2               Q3381 Q3 CH 2 CH 2 SCH 2 CH 2 Q3

382     Q3     CH2CH2、                       Q3382 Q3 CH 2 CH 2 、 Q3

383     Q3     CH2CH2SO2CH2CH2            Q3 383 Q3 CH2CH2SO2CH2CH2Q3 _ _

384     Q3     CH2CH2N(CH3)CH2CH2         Q3384 Q3 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q3

385     Q3     N＝C(CH3)C(CH3)＝N             Q3385 Q3 N=C(CH 3 )C(CH 3 )=N Q3

386     Q3     1，2-C6H4                      Q3386 Q3 1, 2-C 6 H 4 Q3

387     Q3      1，4-C6H4                      Q3387 Q3 1, 4-C 6 H 4 Q3

388     Q3      1，3-C6H4                      Q3388 Q3 1, 3-C 6 H 4 Q3

389     Q3      4-C6H4-4-C6H4-4             Q3389 Q3 4-C 6 H 4 -4-C 6 H 4 -4 Q3

390     Q4      CH2CH2OCH2CH2               Q4390 Q4 CH 2 CH 2 OCH 2 CH 2 Q4

391     Q4      CH2CH2SCH2CH2               Q4391 Q4 CH 2 CH 2 SCH 2 CH 2 Q4

392     Q4      CH2CH2、                       Q4392 Q4 CH 2 CH 2 、 Q4

393     Q4      CH2CH2SO2CH2CH2            Q4 393 Q4 CH2CH2SO2CH2CH2Q4 _ _

394     Q4      CH2CH2N(CH3)CH2CH2         Q4394 Q4 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q4

395     Q4      N＝C(CH3)C(CH3)＝N             Q4395 Q4 N=C(CH 3 )C(CH 3 )=N Q4

396     Q4      1，2-C6H4                      Q4396 Q4 1, 2-C 6 H 4 Q4

397     Q4      1，4-C6H4                      Q4397 Q4 1, 4-C 6 H 4 Q4

398     Q4      1，3-C6H4                      Q4398 Q4 1, 3-C 6 H 4 Q4

399     Q4      4-C6H4-4-C6H4-4             Q4399 Q4 4-C 6 H 4 -4-C 6 H 4 -4 Q4

400     Q5      CH2CH2OCH2CH2               Q5400 Q5 CH 2 CH 2 OCH 2 CH 2 Q5

401     Q5      CH2CH2、                       Q5401 Q5 CH 2 CH 2 、 Q5

402     Q5      CH2CH2SOCH2CH2              Q5402 Q5 CH 2 CH 2 SOCH 2 CH 2 Q5

403     Q5      CH2CH2SO2CH2CH2            Q5 403 Q5 CH2CH2SO2CH2CH2Q5 _ _

404     Q5      CH2CH2N(CH3)CH2CH2         Q5404 Q5 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q5

405     Q5      N＝C(CH3)C(CH3)＝N             Q5405 Q5 N=C(CH 3 )C(CH 3 )=N Q5

406     Q5      1，2-C6H4                      Q5406 Q5 1, 2-C 6 H 4 Q5

407     Q5      1，4-C6H4                      Q5407 Q5 1, 4-C 6 H 4 Q5

408     Q5      1，3-C6H4                      Q5408 Q5 1, 3-C 6 H 4 Q5

409     Q5      4-C6H4-4-C6H4-4             Q5409 Q5 4-C 6 H 4 -4-C 6 H 4 -4 Q5

410     Q6      CH2CH2OCH2CH2               Q6410 Q6 CH 2 CH 2 OCH 2 CH 2 Q6

411     Q6      CH2CH2、                       Q6411 Q6 CH 2 CH 2 、 Q6

412     Q6      CH2CH2SOCH2CH2              Q6412 Q6 CH 2 CH 2 SOCH 2 CH 2 Q6

413     Q6      CH2CH2SO2CH2CH2            Q6413 Q6 CH 2 CH 2 SO 2 CH 2 CH 2 Q6

414     Q6      CH2CH2N(CH3)CH2CH2         Q6414 Q6 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q6

415     Q6      N＝C(CH3)C(CH3)＝N             Q6415 Q6 N=C(CH 3 )C(CH 3 )=N Q6

416     Q6      1，2-C6H4                      Q6416 Q6 1, 2-C 6 H 4 Q6

417     Q6      1，4-C6H4                      Q6417 Q6 1, 4-C 6 H 4 Q6

418     Q6      1，3-C6H4                      Q6418 Q6 1, 3-C 6 H 4 Q6

419     Q6      4-C6H4-4-C6H4-4             Q6419 Q6 4-C 6 H 4 -4-C 6 H 4 -4 Q6

420     Q7      CH2CH2OCH2CH2               Q7420 Q7 CH 2 CH 2 OCH 2 CH 2 Q7

421     Q7      CH2CH2SCH2CH2               Q7421 Q7 CH 2 CH 2 SCH 2 CH 2 Q7

422     Q7     CH2CH2、                        Q7422 Q7 CH 2 CH 2 、 Q7

423     Q7     CH2CH2SO2CH2CH2             Q7423 Q7 CH 2 CH 2 SO 2 CH 2 CH 2 Q7

424     Q7     CH2CH2N(CH3)CH2CH2          Q7424 Q7 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q7

425     Q7     N＝C(CH3)C(CH3)＝N              Q7425 Q7 N=C(CH 3 )C(CH 3 )=N Q7

426     Q7     1，2-C6H4                       Q7426 Q7 1, 2-C 6 H 4 Q7

427     Q7     1，4-C6H4                       Q7427 Q7 1, 4-C 6 H 4 Q7

428     Q7     1，3-C6H4                       Q7428 Q7 1, 3-C 6 H 4 Q7

429     Q7     4-C6H4-4-C6H4-4              Q7429 Q7 4-C 6 H 4 -4-C 6 H 4 -4 Q7

430     Q8     CH2CH2OCH2CH2                Q8430 Q8 CH 2 CH 2 OCH 2 CH 2 Q8

431     Q8     CH2CH2、                        Q8431 Q8 CH 2 CH 2 、 Q8

432     Q8     CH2CH2SOCH2CH2               Q8432 Q8 CH 2 CH 2 SOCH 2 CH 2 Q8

433     Q8     CH2CH2SO2CH2CH2             Q8 433 Q8 CH2CH2SO2CH2CH2Q8 _ _

434     Q8     CH2CH2N(CH3)CH2CH2          Q8434 Q8 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q8

435     Q8     N＝C(CH3)C(CH3)＝N              Q8435 Q8 N=C(CH 3 )C(CH 3 )=N Q8

436     Q8     1，2-C6H4                       Q8436 Q8 1, 2-C 6 H 4 Q8

437     Q8     1，4-C6H4                       Q8437 Q8 1, 4-C 6 H 4 Q8

438     Q8     1，3-C6H4                       Q8438 Q8 1, 3-C 6 H 4 Q8

439     Q8     4-C6H4-4-C6H4-4              Q8439 Q8 4-C 6 H 4 -4-C 6 H 4 -4 Q8

440     Q9     CH2CH2OCH2CH2                Q9440 Q9 CH 2 CH 2 OCH 2 CH 2 Q9

441     Q9     CH2CH2SCH2CH2                Q9441 Q9 CH 2 CH 2 SCH 2 CH 2 Q9

442     Q9     CH2CH2、                        Q9442 Q9 CH 2 CH 2 、 Q9

443     Q9     CH2CH2SO2CH2CH2             Q9443 Q9 CH 2 CH 2 SO 2 CH 2 CH 2 Q9

444     Q9     CH2CH2N(CH3)CH2CH2          Q9444 Q9 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q9

445     Q9     N＝C(CH3)C(CH3)＝N              Q9445 Q9 N=C(CH 3 )C(CH 3 )=N Q9

446     Q9     1，2-C6H4                       Q9446 Q9 1, 2-C 6 H 4 Q9

447     Q9     1，4-C6H4                       Q9447 Q9 1, 4-C 6 H 4 Q9

448     Q9     1，3-C6H4                       Q9448 Q9 1, 3-C 6 H 4 Q9

449     Q9     4-C6H4-4-C6H4-4              Q9449 Q9 4-C 6 H 4 -4-C 6 H 4 -4 Q9

450     Q10    CH2CH2OCH2CH2                Q10450 Q10 CH 2 CH 2 OCH 2 CH 2 Q10

451     Q10    CH2CH2SCH2CH2                Q10451 Q10 CH 2 CH 2 SCH 2 CH 2 Q10

452     Q10    CH2CH2、                        Q10452 Q10 CH 2 CH 2 、 Q10

453     Q10    CH2CH2SO2CH2CH2             Q10 453 Q10 CH2CH2SO2CH2CH2Q10 _ _

454     Q10    CH2CH2N(CH3)CH2CH2          Q10454 Q10 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q10

455     Q10    N＝C(CH3)C(CH3)＝N              Q10455 Q10 N=C(CH 3 )C(CH 3 )=N Q10

456     Q10    1，2-C6H4                       Q10456 Q10 1, 2-C 6 H 4 Q10

457     Q10     1，4-C6H4                 Q10457 Q10 1, 4-C 6 H 4 Q10

458     Q10     1，3-C6H4                 Q10458 Q10 1, 3-C 6 H 4 Q10

459     Q10     4-C6H4-4-C6H4-4        Q10459 Q10 4-C 6 H 4 -4-C 6 H 4 -4 Q10

460     Q11     CH2CH2OCH2CH2          Q11460 Q11 CH 2 CH 2 OCH 2 CH 2 Q11

461     Q11     CH2CH2SCH2CH2          Q11461 Q11 CH 2 CH 2 SCH 2 CH 2 Q11

462     Q11     CH2CH2SOCH2CH2         Q11462 Q11 CH 2 CH 2 SOCH 2 CH 2 Q11

463     Q11     CH2CH2SO2CH2CH2       Q11 463 Q11 CH2CH2SO2CH2CH2Q11 _ _

464     Q11     CH2CH2N(CH3)CH2CH2    Q11464 Q11 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q11

465     Q11     N＝C(CH3)C(CH3)＝N        Q11465 Q11 N=C(CH 3 )C(CH 3 )=N Q11

466     Q11     1，2-C6H4                 Q11466 Q11 1, 2-C 6 H 4 Q11

467     Q11     1，4-C6H4                 Q11467 Q11 1, 4-C 6 H 4 Q11

468     Q11     1，3-C6H4                 Q11468 Q11 1, 3-C 6 H 4 Q11

469     Q11     4-C6H4-4-C6H4-4        Q11469 Q11 4-C 6 H 4 -4-C 6 H 4 -4 Q11

470     Q12     CH2CH2OCH2CH2          Q12470 Q12 CH 2 CH 2 OCH 2 CH 2 Q12

471     Q12     CH2CH2SCH2CH2          Q12471 Q12 CH 2 CH 2 SCH 2 CH 2 Q12

472     Q12     CH2CH2、                  Q12472 Q12 CH 2 CH 2 、 Q12

473     Q12     CH2CH2SQ2CH2CH2       Q12473 Q12 CH 2 CH 2 SQ 2 CH 2 CH 2 Q12

474     Q12     CH2CH2N(CH3)CH2CH2    Q12474 Q12 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q12

475     Q12     N＝C(CH3)C(CH3)＝N        Q12475 Q12 N=C(CH 3 )C(CH 3 )=N Q12

476     Q12     1，2-C6H4                 Q12476 Q12 1, 2-C 6 H 4 Q12

477     Q12     1，4-C6H4                 Q12477 Q12 1, 4-C 6 H 4 Q12

478     Q12     1，3-C6H4                 Q12478 Q12 1, 3-C 6 H 4 Q12

479     Q12     4-C6H4-4-C6H4-4        Q12479 Q12 4-C 6 H 4 -4-C 6 H 4 -4 Q12

480     Q13     CH2CH2OCH2CH2          Q13480 Q13 CH 2 CH 2 OCH 2 CH 2 Q13

481     Q13     CH2CH2SCH2CH2          Q13481 Q13 CH 2 CH 2 SCH 2 CH 2 Q13

482     Q13     CH2CH2、                  Q13482 Q13 CH 2 CH 2 、 Q13

483     Q13     CH2CH2SO2CH2CH2       Q13 483 Q13 CH2CH2SO2CH2CH2Q13 _ _

484     Q13     CH2CH2N(CH3)CH2CH2    Q13484 Q13 CH 2 CH 2 N(CH 3 )CH 2 CH 2 Q13

485     Q13     N＝C(CH3)C(CH3)＝N        Q13485 Q13 N=C(CH 3 )C(CH 3 )=N Q13

486     Q13     1，2-C6H4                 Q13486 Q13 1, 2-C 6 H 4 Q13

487     Q13     1，4-C6H4                 Q13487 Q13 1, 4-C 6 H 4 Q13

488     Q13     1，3-C6H4                 Q13488 Q13 1, 3-C 6 H 4 Q13

489     Q13     4-C6H4-4-C6H4-4        Q13489 Q13 4-C 6 H 4 -4-C 6 H 4 -4 Q13

通式I所表达的化合物作为除草剂的有效成分是有用的。当本发明通式I的化合物作为除草剂，有效成分适合的剂型取决于具体目的和合适的施用方法。因此本发明还包括由通式I所表示的一种具有除草活性的新型羧酸酯类化合物与农业上可应用的载体所形成的除草组合物。The compounds expressed by the general formula I are useful as active ingredients of herbicides. When the compound of the general formula I of the present invention is used as a herbicide, the suitable dosage form of the active ingredient depends on the specific purpose and suitable application method. Therefore, the present invention also includes a herbicidal composition formed from a novel carboxylate compound with herbicidal activity represented by general formula I and an agriculturally applicable carrier.

一般来说，有效成分用惰性溶剂和固体载体溶解或稀释。所应用的剂型有粉剂，可湿性粉剂，乳油，水剂及油悬剂，粒剂，胶囊剂等，通常需要加入表面活性剂或其它助剂。此外本发明化合物可与杀虫剂、杀线虫剂、杀菌剂及其它除草剂，植物生长调节剂，肥料等混用。Generally, the active ingredient is dissolved or diluted with an inert solvent and a solid carrier. The dosage forms used include powder, wettable powder, emulsifiable concentrate, water and oil suspension, granule, capsule, etc., usually need to add surfactant or other auxiliary agents. In addition, the compounds of the present invention can be mixed with insecticides, nematicides, fungicides and other herbicides, plant growth regulators, fertilizers and the like.

本发明化合物可用作单剂或混剂。单剂和混剂的制备方法见《Pesticidal FormulationResearch》(1969)，Advances in Chemistry Series No.86，Wade Van Valkenburg；《PesticideFormulations》(1973)Wade Van Valkenburg。在这些单剂和混剂中，活性成分与常规的农业上可以接受的惰性的稀释剂或表面活性剂如固体载体或液体载体混配。载体既可以溶解、分散有效成分又不影响有效成分的活性，并且其本身对土壤、设备、作物或农业环境无明显损害作用。单剂和混剂中助剂一般为表面活性剂，稳定剂，消泡剂或分散剂。本发明的单剂和混剂也包括同已知的农药化合物的混配，其目的在于扩大制剂的活性范围并提高药效。The compounds of the present invention can be used as a single agent or in combination. For the preparation methods of single agent and mixed agent, see "Pesticide Formulation Research" (1969), Advances in Chemistry Series No.86, Wade Van Valkenburg; "PesticideFormulations" (1973) Wade Van Valkenburg. In these single formulations and mixtures, the active ingredients are mixed with conventional agriculturally acceptable inert diluents or surface active agents such as solid carriers or liquid carriers. The carrier can dissolve and disperse the active ingredient without affecting the activity of the active ingredient, and itself has no obvious damage to the soil, equipment, crops or agricultural environment. Auxiliaries in single agent and mixed agent are generally surfactants, stabilizers, defoamers or dispersants. The single agent and mixed agent of the present invention also include mixing with known pesticide compounds, the purpose of which is to expand the active range of the preparation and improve the efficacy.

制剂中有效成分其重量百分含量为0.1％到99％，并含有至少0.1％到20％的表现活性剂和0.1％到99％固体或液体稀释剂。The active ingredient in the preparation is 0.1% to 99% by weight, and contains at least 0.1% to 20% of performance active agent and 0.1% to 99% of solid or liquid diluent.

如果通式I的化合物与另一除草剂相混，根据活性化合物、应用目的、环境条件及剂型的不同，混剂中有效成分的含量变化范围很大。混剂中有效成分含量一般在1％到95％，较适宜的含量在5％到60％。本发明化合物的有效剂量范围一般为1克/公顷到3千克/公顷，5克/公顷到500克/公顷较好。If the compound of the general formula I is mixed with another herbicide, the content of the active ingredient in the mixture can vary widely depending on the active compound, application purpose, environmental conditions and dosage form. The content of active ingredients in the mixture is generally 1% to 95%, and the suitable content is 5% to 60%. The effective dose of the compound of the present invention is generally in the range of 1 g/ha to 3 kg/ha, preferably 5 g/ha to 500 g/ha.

本发明另外的实施方案为防治目标作物田(如小麦、玉米、大豆、棉花、花生、蔬菜和水稻等田中)中杂草的方法，该方法包括将除草有效量的通式I所示化合物与可接受的载体组成的新型羧酸酯类化合物除草组合物施于所述的杂草、所述杂草的场所或所述杂草的生长介质的表面上。Another embodiment of the present invention is a method for controlling weeds in target crop fields (such as fields such as wheat, corn, soybean, cotton, peanut, vegetables and rice), the method comprising combining a herbicidally effective amount of a compound represented by general formula I with The novel carboxylate compound herbicidal composition composed of an acceptable carrier is applied to the weeds, the site of the weeds or the surface of the growth medium of the weeds.

具体实施方式Detailed ways

下面以制备和制剂的实例对本发明进行更详细的说明。但应指出，本发明绝不仅限于这些具体的例子。在制剂的例子中，“份”表示重量份数，制剂的含量为重量百分含量，化合物编号与表1-2中的一致。The present invention will be described in more detail with the examples of preparation and formulation below. However, it should be noted that the present invention is by no means limited to these specific examples. In the examples of preparations, "parts" means parts by weight, the content of the preparations is percentage by weight, and the compound numbers are consistent with those in Table 1-2.

制备例1(第2号化合物)Preparation Example 1 (Compound No. 2)

1.0克取代的苯氧丙酰氯(结构式中R表示为旋光异构体R型，下同)与3.0克苯乙醇在50毫升甲苯中加热回流4小时，冷却后，真空加热脱去甲苯，加水和乙酸乙酯，分出有机层，并用水和盐水洗涤，干燥后浓缩。剩余物用硅胶柱层析纯化得0.5克油状物。1.0 grams of substituted phenoxypropionyl chloride (R in the structural formula represents the optical isomer R type, the same below) and 3.0 grams of phenethyl alcohol were heated to reflux in 50 milliliters of toluene for 4 hours, after cooling, the toluene was removed by vacuum heating, water was added and Ethyl acetate, the organic layer was separated, washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to obtain 0.5 g of an oily substance.

1H NMR(CDCl3)：8.48(s，1H)，7.87(d，1H)，7.46(m，2H)，7.08～6.91(m，8H)，6.81(s，1H)，4.58(q，1H)，4.32(t，2H)，2.89(t，2H)，1.56(d，3H)。 1 H NMR (CDCl 3 ): 8.48(s, 1H), 7.87(d, 1H), 7.46(m, 2H), 7.08～6.91(m, 8H), 6.81(s, 1H), 4.58(q, 1H ), 4.32(t, 2H), 2.89(t, 2H), 1.56(d, 3H).

制备例2(第20号化合物)Preparation Example 2 (Compound No. 20)

2.1克取代的苯氧丙酰氯与0.5克丁二酮肟在50毫升甲苯中加热至80℃反应8小时，冷却后，真空加热脱去甲苯，加水和乙酸乙酯，分出有机层，并用水和盐水洗涤，干燥后浓缩。剩余物用硅胶柱层析纯化得0.5克目的物，熔点116～119℃。2.1 g of substituted phenoxypropionyl chloride and 0.5 g of dimethylglyoxime were heated to 80 ° C in 50 ml of toluene to react for 8 hours. After cooling, the toluene was removed by vacuum heating, water and ethyl acetate were added, the organic layer was separated, and water Washed with brine, dried and concentrated. The residue was purified by silica gel column chromatography to obtain 0.5 g of the target product, melting point 116-119°C.

1H NMR(CDCl3)：8.69(s，1H)，8.07(1H)，8.00(2H)，7.68(1H)，7.60(1H)，7.18(2H)，4.84(m，1H)，3.74(s，6H)，1.72(d，3H)。 1 H NMR (CDCl 3 ): 8.69(s, 1H), 8.07(1H), 8.00(2H), 7.68(1H), 7.60(1H), 7.18(2H), 4.84(m, 1H), 3.74(s , 6H), 1.72 (d, 3H).

制备例3(第367号化合物)Preparation Example 3 (Compound No. 367)

Figure A0314337500322
Figure A0314337500322

2.2克取代的苯氧丙酰氯与0.3克对苯二酚在50毫升甲苯中于35～40℃搅拌8小时，真空加热脱去甲苯，加水和乙酸乙酯，分出有机层，并用水和盐水洗涤，干燥后浓缩。剩余物用硅胶柱层析纯化得0.5克目的物，熔点121～125℃。2.2 g of substituted phenoxypropionyl chloride and 0.3 g of hydroquinone were stirred in 50 ml of toluene at 35-40°C for 8 hours, heated in vacuum to remove the toluene, added water and ethyl acetate, separated the organic layer, and mixed with water and brine Washed, dried and concentrated. The residue was purified by silica gel column chromatography to obtain 0.5 g of the target product, melting point 121-125°C.

制备例4(第365号化合物)Preparation Example 4 (Compound No. 365)

Figure A0314337500323
Figure A0314337500323

4.0克取代的苯氧丙酰氯与0.3克丁二酮二肟在50毫升甲苯中加热至80℃反应8小时，冷却后，真空加热脱去甲苯，加水和乙酸乙酯，分出有机层，并用水和盐水洗涤，干燥后浓缩。剩余物用硅胶柱层析纯化得0.5克目的物，熔点149～151℃。4.0 g of substituted phenoxypropionyl chloride and 0.3 g of diacetyldioxime were heated to 80°C in 50 ml of toluene to react for 8 hours. After cooling, the toluene was removed by vacuum heating, water and ethyl acetate were added, the organic layer was separated, and Washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to obtain 0.5 g of the target product, melting point 149-151°C.

制备例5(第33号化合物)Preparation Example 5 (Compound No. 33)

1.7克取代的苯氧丙酰氯溶于二氯甲烷中，滴加到0.4克2，4-戊二酮和0.6克三乙胺的二氯甲烷中，室温反应4小时，冷却后，真空加热脱去甲苯，加水和乙酸乙酯，分出有机层，并用水和盐水洗涤，干燥后浓缩。剩余物用硅胶柱层析纯化得0.3克目的物，熔点66～68℃。1.7 g of substituted phenoxypropionyl chloride was dissolved in dichloromethane, added dropwise to 0.4 g of 2,4-pentanedione and 0.6 g of triethylamine in dichloromethane, and reacted at room temperature for 4 hours. Toluene was removed, water and ethyl acetate were added, the organic layer was separated, washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to obtain 0.3 g of the desired product, melting point 66-68°C.

同法可合成表1和表2所示的化合物。Compounds shown in Table 1 and Table 2 can be synthesized in the same way.

部分化合物的物理性质如下：第360号化合物 熔点81～84℃，第362号化合物 熔点139～141℃，第25、30、361号化合物为油状物。The physical properties of some compounds are as follows: Compound No. 360 has a melting point of 81-84°C, compound No. 362 has a melting point of 139-141°C, and compounds No. 25, 30, and 361 are oily substances.

制剂实例1Formulation example 1

第20号化合物50份，聚氧乙烯烷芳醚5份，十二烷基苯磺酸钠盐份5份，人造水合二氧化硅40份磨细并充分混匀，即得50％可湿性粉。50 parts of compound No. 20, 5 parts of polyoxyethylene alkaryl ether, 5 parts of sodium dodecylbenzenesulfonate, 40 parts of artificial hydrated silicon dioxide, ground and fully mixed to obtain 50% wettable powder .

化合物表中任一固体化合物可按上述方法制得50％可湿性粉。Any solid compound in the compound table can be prepared as 50% wettable powder according to the above method.

制剂实例2aFormulation Example 2a

第2化合物10份，聚氧乙烯烷芳醚6份，十二烷基苯磺酸钠盐4份，二甲苯30份和环已酮50份磨细并充分混匀，即得10％的乳油。10 parts of the second compound, 6 parts of polyoxyethylene alkaryl ether, 4 parts of sodium dodecylbenzenesulfonate, 30 parts of xylene and 50 parts of cyclohexanone, ground and fully mixed to obtain 10% emulsifiable concentrate .

制剂实例2b-jFormulation Examples 2b-j

制备方法及加料量同上，仅将活性组分依次换成第20、25、30、33、360、361、362、365、367号化合物。The preparation method and dosage are the same as above, only the active components are replaced by No. 20, 25, 30, 33, 360, 361, 362, 365, and 367 compounds in sequence.

制剂实例3aFormulation Example 3a

第362号化合物20份，人造水合二氧化硅2份，聚氧乙烯脱水山梨(糖)醇一油酸3份，羧甲基纤维素5份磨细并和70份水充分混匀，且使有效成分粒子小于5微米，即得20％的水悬浮剂。20 parts of No. 362 compound, 2 parts of artificial hydrated silicon dioxide, 3 parts of polyoxyethylene sorbitan (sugar) monooleic acid, 5 parts of carboxymethyl cellulose are ground and fully mixed with 70 parts of water, and make The particle size of the active ingredient is less than 5 microns, that is, a 20% water suspension can be obtained.

制剂实例3b-dFormulation Examples 3b-d

制备方法及加料量同上，仅将活性组分依次换成第360、365、367号化合物。The preparation method and dosage are the same as above, only the active components are replaced by No. 360, No. 365 and No. 367 compounds in turn.

制剂实例4aFormulation Example 4a

第365号化合物5份，异丙酸磷酸盐1份，高岭土64份和30份滑石粉磨细并充分混匀，且使有效成分粒子小于5微米，即得5％的粉剂。5 parts of No. 365 compound, 1 part of isopropionic acid phosphate, 64 parts of kaolin and 30 parts of talcum powder were ground and fully mixed, and the particles of the active ingredient were smaller than 5 microns to obtain a 5% powder.

制剂实例4b-dFormulation Examples 4b-d

制备方法及加料量同上，仅将活性组分依次换成第360、362、367号化合物。The preparation method and dosage are the same as above, only the active components are replaced by No. 360, No. 362 and No. 367 compounds in turn.

制剂实例5aFormulation Example 5a

第367号化合物25份，聚氧乙稀脱水山梨(糖)醇一油酸3份，聚乙稀醇2份磨细并和70份水充分混匀，且有效成分粒子小于5微米，即得25％水悬浮剂。25 parts of No. 367 compound, 3 parts of polyoxyethylene sorbitan monooleic acid, 2 parts of polyvinyl alcohol are ground and fully mixed with 70 parts of water, and the active ingredient particles are less than 5 microns, to obtain final product 25% water suspension.

制剂实例5b-dFormulation Examples 5b-d

制备方法及加料量同上，仅将活性组分依次换成第360、362、365号化合物。The preparation method and dosage are the same as above, only the active components are replaced by No. 360, No. 362 and No. 365 compounds in turn.

生物活性测定Bioactivity assay

以阔叶杂草决明(Cassia tora)、苘麻(Abutilon theophrasti)、百日草(Zinnia elegans Jacq)，单子叶杂草稗草(Echinochloa crus-galli)、马唐(Digtaria sanguinalis)、狗尾草(Setaria viridis)，和作物如小麦、玉米、水稻、大豆和棉花为测试对象，对上述化合物进行测定。Broadleaf weeds Cassia tora, Abutilon theophrasti, Zinnia elegans Jacq, monocot weeds Echinochloa crus-galli, crabgrass (Digtaria sanguinalis), foxtail ( Setaria viridis), and crops such as wheat, corn, rice, soybean and cotton as test objects, the above compounds were determined.

按照下列程序对每一化合物进行测定。Each compound was assayed according to the following procedure.

苗后测定，种子发芽并生长10-21天，使处理前具有一系列生育阶段的试材。选择大小、生育阶段一致的试材，进行处理，处理置于温室并浇水。未用化合物处理的试材作对照。Post-emergence measurement, the seeds germinate and grow for 10-21 days, so that the test materials have a series of growth stages before treatment. The test materials with the same size and growth stage were selected and treated, and the treated materials were placed in the greenhouse and watered. Samples not treated with compounds were used as controls.

待测化合物用合适溶剂(一般用丙酮)溶解，其制剂直接用水溶解，然后进行喷雾处理，喷液量为187或468L/公顷，有效剂量为g/ha。于处理后2周或4周调查，药剂对每一试材的活性以0-100分级，0表示无活性，100表示完全抑制。The compound to be tested is dissolved with a suitable solvent (generally acetone), and its preparation is directly dissolved in water, and then sprayed. The spray volume is 187 or 468 L/ha, and the effective dose is g/ha. After 2 weeks or 4 weeks of investigation, the activity of the agent on each test material was graded on a scale of 0-100, with 0 indicating no activity and 100 indicating complete inhibition.

在600g/ha部分测试结果(第2、20、25、30、34、36、360、361、362、365、367号任一化合物)，对阔叶作物如大豆、棉花等安全。Partial test results at 600g/ha (compound No. 2, 20, 25, 30, 34, 36, 360, 361, 362, 365, 367), safe for broad-leaved crops such as soybeans and cotton.

部分测试化合物对苗后杂草防除效果见表3：The post-emergence weed control effects of some test compounds are shown in Table 3:

                                            表3 table 3

化合物      剂量g/ha   稗草     马唐     狗尾草      决明      苘麻      百日草Compound Dosage g/ha Barnyard Grass Crabgrass Setaria Cassia Abutilon Zinnia

2             300      100     100       100         0         0          02 300 100 100 100 0 0 0 0

20            300      100     100       100         0         0          020 300 100 100 100 0 0 0 0

25            300      100     100       100         0         0          025 300 100 100 100 0 0 0 0

30            300      100     100       100         0         0          030 300 100 100 100 0 0 0 0

33            300      100     100       100         0         0          033 300 100 100 100 0 0 0 0

34            300      100     100       100         0         0          034 300 100 100 100 0 0 0 0

36            300      100     100       100         0         0          036 300 100 100 100 0 0 0 0

360           100      100      99        90         0         0          0360 100 100 99 90 0 0 0 0

              12.5     100      90        85         0         0          012.5 100 90 85 0 0 0 0

361           100      100      90        75         0         0          0361 100 100 90 75 0 0 0 0

              12.5      75      80        65         0         0          012.5 75 80 65 0 0 0 0

362           100      100      99       100         0         0          0362 100 100 99 100 0 0 0 0

              12.5     100      98        85         0         0          012.5 100 98 85 0 0 0 0

365           300      100     100       100         0         0          0365 300 100 100 100 0 0 0 0

367           300      100     100       100         0         0          0367 300 100 100 100 0 0 0 0

Claims (9)

1. novel carboxylic acid ester compound, shown in general formula I I:
Figure A031433750002C1
In the formula:
X-X 1-Z is selected from one of following group:
CH 2CH 2OR 1，CH 2CH 2R 1，CH 2CO-R 1，CH 2CH 2SR 1，
Figure A031433750002C3
When-X-is selected from CH 2CH 2OCH 2CH 2, CH 2CH 2SCH 2CH 2, CH 2CH 2N (CH 3) CH 2CH 2,
CH 2CH 2, CH 2CH 2SO 2CH 2CH 2Or CH 2CH 2SOCH 2CH 2The time, X 1Be selected from O, Z is selected from Q;
Wherein:
R 1, R 2Can be identical or different, be selected from H respectively, halogen, CN, CO 2R 3, CONR 2R 3, CHR 2CO 2R 3, CHR 2CONR 2R 3, C 1-C 12Alkyl, ring C 3-C 8Alkyl, C 2-C 12Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 12Alkynyl, halo C 1-C 12Alkyl, halo C 2-C 12Thiazolinyl, halo C 2-C 12Alkynyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, C 1-C 12Alkyl sulphonyl C 1-C 12Alkyl, C 1-C 12Alkyl sulphinyl C 1-C 12Alkyl, C 1-C 12Alkyl sulfonyl basic ring C 3-C 8Alkyl, C 1-C 12Alkyl sulfenyl ring C 3-C 8Alkyl, cyano group C 1-C 12Alkoxyl group, cyano group C 1-C 12Alkyl, cyano group ring C 3-C 8Alkyl, halo C 1-C 12Alkoxyl group, halo C 1-C 12Alkylthio, halo ring C 3-C 8Alkane, aryl, heteroaryl, aryl C 1-C 12Alkyl or heteroaryl C 2-C 12Alkyl, all these groups can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C 1-C 12Alkyl, ring C 3-C 8Alkyl, C 2-C 12Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 12Alkynyl, halo C 1-C 12Alkyl, halo C 2-C 12Thiazolinyl, halo C 2-C 12Alkynyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, C 1-C 12Alkyl sulphonyl, C 1-C 12Alkyl sulphinyl, phenyl, benzene is for C 1-C 12Alkyl, benzene is for C 2-C 12Thiazolinyl, benzene is for C 2-C 12Alkynyl, cyano group or halo C 1-C 12Alkoxyl group, all these groups can also further be replaced;
R 3And R 4Identical or different, be selected from H respectively, CO 2R 3, CONR 2R 3, CHR 2CO 2R 3, CHR 2CONR 2R 3, C 1-C 12Alkyl, ring C 3-C 8Alkyl, C 2-C 12Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 12Alkynyl, halo C 1-C 12Alkyl, halo C 2-C 12Thiazolinyl, halo C 2-C 12Alkynyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, C 1-C 12Alkyl sulphonyl C 1-C 12Alkyl, C 1-C 12Alkyl sulphinyl C 1-C 12Alkyl, C 1-C 12Alkyl sulfonyl basic ring C 3-C 8Alkyl, C 1-C 12Alkyl sulfenyl ring C 3-C 8Alkyl, cyano group C 1-C 12Alkoxyl group, cyano group C 1-C 12Alkyl, cyano group ring C 3-C 8Alkyl, halo C 1-C 12Alkoxyl group, halo C 1-C 12Alkylthio, halo ring C 3-C 8Alkane, aryl, heteroaryl, aryl C 1-C 12Alkyl or heteroaryl C 2-C 12) base, all these groups can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C 1-C 12Alkyl, ring C 3-C 8Alkyl, C 2-C 12Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 12Alkynyl, halo C 1-C 12Alkyl, halo C 2-C 12Thiazolinyl, halo C 2-C 12Alkynyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, C 1-C 12Alkyl sulphonyl, C 1-C 12Alkyl sulphinyl, phenyl, substituted-phenyl, benzene are for C 1-C 12Alkyl, benzene is for C 2-C 12Thiazolinyl, benzene is for C 2-C 12Alkynyl, cyano group or halo C 1-C 12Alkoxyl group, all these groups can also further be replaced;
NR 3R 4, NR 2R 3Can form five circle or six annulus respectively; Perhaps also can be
Figure A031433750003C1
Wherein: R 5Be R 1, R 6Be R 2R 5And R 6Can also form five circle or six annulus;
Q is selected from Q1, Q2, and Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13:
2. according to the described compound of claim 1, it is characterized in that: among the general formula compound I
X-X 1-Z is selected from one of following group:
Figure A031433750004C2
CH 2CH 2OR 1，CH 2CH 2R 1，CH 2CO-R 1，CH 2CH 2SR 1，
When-X-is selected from CH 2CH 2OCH 2CH 2, CH 2CH 2SCH 2CH 2, CH 2CH 2N (CH 3) CH 2CH 2,
CH 2CH 2, CH 2CH 2SO 2CH 2CH 2Or CH 2CH 2SOCH 2CH 2The time, X 1Be selected from O, Z is selected from Q.
Wherein:
R 1, R 2Can be identical or different, be selected from H respectively, bromine, chlorine, fluorine, CN, CO 2R 3, CONR 2R 3, CHR 2CO 2R 3, CHR 2CONR 2R 3, C 1-C 6Alkyl, ring C 5-C 6Alkyl, C 2-C 6Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 6Alkynyl, halo C 1-C 6Alkyl, halo C 2-C 6Thiazolinyl, halo C 2-C 6Alkynyl, C 1-C 6Alkoxyl group, C 1-C 6Alkylthio, aryl, heteroaryl, aryl C 1-C 12Alkyl or heteroaryl C 2-C 12Alkyl, wherein aryl or heteroaryl are furans, naphthalene, phenyl, pyrazoles, pyridine, pyrimidine, thiophene or triazole; Aryl or heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C 1-C 12Alkyl, ring C 3-C 8Alkyl, C 2-C 12Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 12Alkynyl, halo C 1-C 12Alkyl, halo C 2-C 12Thiazolinyl, halo C 2-C 12Alkynyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, C 1-C 12Alkyl sulphonyl, C 1-C 12Alkyl sulphinyl, phenyl, benzene is for C 1-C 12Alkyl, benzene is for C 2-C 12Thiazolinyl, benzene is for C 2-C 12Alkynyl, cyano group or halo C 1-C 12Alkoxyl group, all these groups can also further be replaced;
R 3And R 4Can be identical or different, be selected from H respectively, CO 2R 3, CONR 2R 3, CHR 2CO 2R 3, CHR 2CONR 2R 3, C 1-C 6Alkyl, ring C 5-C 6Alkyl, C 2-C 6Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 6Alkynyl, halo C 1-C 6Alkyl, halo C 2-C 6Thiazolinyl, halo C 2-C 6Alkynyl, C 1-C 6Alkoxyl group, C 1-C 6Alkylthio, aryl, heteroaryl, aryl C 1-C 12Alkyl or heteroaryl C 2-C 12Alkyl, wherein aryl or heteroaryl are furans, naphthalene, phenyl, pyrazoles, pyridine, pyrimidine, thiophene or triazole, aryl or heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C 1-C 12Alkyl, ring C 3-C 8Alkyl, C 2-C 12Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 12Alkynyl, halo C 1-C 12Alkyl, halo C 2-C 12Thiazolinyl, halo C 2-C 12Alkynyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, C 1-C 12Alkyl sulphonyl, C 1-C 12Alkyl sulphinyl, phenyl, benzene is for C 1-C 12Alkyl, benzene is for C 2-C 12Thiazolinyl, benzene is for C 2-C 12Alkynyl, cyano group or halo C 1-C 12Alkoxyl group, all these groups can also further be replaced.
NR 3R 4, NR 2R 3Can form five circle or six annulus respectively; Perhaps also can be
Figure A031433750005C1
Wherein: R 5Be R 1, R 6Be R 2R 5And R 6Can also form five circle or six annulus;
Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13.
3. according to the described compound of claim 2, it is characterized in that: among the general formula compound I
X-X 1-Z is selected from one of following group:
CH 2CH 2OR 1，CH 2CH 2R 1，CH 2CO-R 1，CH 2CH 2SR 1，
Figure A031433750005C3
When-X-is selected from CH 2CH 2OCH 2CH 2, CH 2CH 2SCH 2CH 2, CH 2CH 2N (CH 3) CH 2CH 2,
CH 2CH 2, CH 2CH 2SO 2CH 2CH 2Or CH 2CH 2SOCH 2CH 2The time, X 1Be selected from O, Z is selected from Q;
Wherein:
R 1, R 2Can be identical or different, be selected from H respectively, bromine, chlorine, fluorine, CN, CO 2R 3, CONR 2R 3, CHR 2CO 2R 3, CHR 2CONR 2R 3, C 1-C 6Alkyl, ring C 5-C 6Alkyl, C 2-C 6Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 6Alkynyl, halo C 1-C 6Alkyl, halo C 2-C 6Thiazolinyl, halo C 2-C 6) alkynyl, C 1-C 6Alkoxyl group, C 1-C 6Alkylthio, aryl, heteroaryl, aryl C 1-C 12Alkyl or heteroaryl C 2-C 12Alkyl, wherein aryl or heteroaryl are selected from furans, phenyl or pyridine; Aryl or heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C 1-C 12Alkyl, ring C 3-C 8Alkyl, halo C 1-C 12Alkyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, C 1-C 12Alkyl sulphonyl, phenyl, benzene is for C 1-C 12Alkyl, cyano group or halo C 1-C 12Alkoxyl group, all these groups can also further be replaced;
R 3And R 4Identical or different is H, CO 2R 3, CONR 2R 3, CHR 2CO 2R 3, CHR 2CONR 2R 3, C 1-C 6Alkyl, ring C 5-C 6Alkyl, C 2-C 6Thiazolinyl, ring C 3-C 8Thiazolinyl, C 2-C 6Alkynyl, halo C 1-C 6Alkyl, halo C 2-C 6Thiazolinyl, halo C 2-C 6Alkynyl, C 1-C 6Alkoxyl group, C 1-C 6Alkylthio, aryl, heteroaryl, aryl C 1-C 12Alkyl or heteroaryl C 2-C 12Alkyl, wherein aryl or heteroaryl are selected from furans, phenyl or pyridine; Aryl and heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C 1-C 12Alkyl, ring C 3-C 8Alkyl, halo C 1-C 12Alkyl, C 1-C 12Alkoxyl group, C 1-C 12Alkylthio, phenyl, benzene is for C 1-C 12Alkyl, cyano group or halo C 1-C 12Alkoxyl group, all these groups can also further be replaced;
NR 3R 4, NR 2R 3Can form Pyrrolidine, morpholine or hexahydropyridine respectively; Perhaps also can be
Wherein: R 5Be R 1, R 6Be R 2R 5And R 6All right makeup ring pentane or hexanaphthene;
Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13.
4. according to the described compound of claim 3, it is characterized in that: among the general formula compound I
X-X 1-Z is selected from:
CH 2CH 2R 1, Or
When-X-is selected from:
CH 2CH 2，CH 2CH 2OCH 2CH 2，CH 2CH 2SCH 2CH 2
Or
The time, X 1Be selected from O, Z is selected from Q1, Q3, Q4 or Q6; Wherein, R 1, R 2, R 3Can be identical or different, be selected from H, C respectively 1-C 4Alkyl, phenyl, halogenophenyl or
Figure A031433750006C7
5. the purposes of the described compound of claim 1 aspect management of weeds.
6. herbicidal composition, it is characterized in that: the active ingredient in the said composition is the compound described in the claim 1, weight content is 0.1% to 99%.
7. according to the described herbicidal composition of claim 6, it is characterized in that: also contain agricultural in the composition and go up applicable carrier.
8. according to the described herbicidal composition of claim 6, it is characterized in that: the agricultural chemicals or the fertilizer that can also contain other in the said composition.
9. the method for a management of weeds, it is characterized in that: weeds, weed growth ground or weed growth medium to farm crop Tanaka are used herbicidal composition as claimed in claim 6.
CN 03143375 2003-09-29 2003-09-29 Novel carboxylate herbicides Expired - Lifetime CN1281602C (en)

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CN104803987A (en) * 2014-01-28 2015-07-29 中国中化股份有限公司 Oxime-containing carboxylate compound and use thereof
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CN106632097A (en) * 2016-12-15 2017-05-10 三峡大学 Condensed heterogeneous oxyphenoxy carboxylic acid derivative and application thereof
CN106632293A (en) * 2016-12-15 2017-05-10 三峡大学 Aryloxyphenoxy alkane acid derivative with biological activity and preparation method thereof
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