CN1051994C - 异羟肟酸衍生物,其制备方法和作为杀菌剂之应用 - Google Patents
异羟肟酸衍生物,其制备方法和作为杀菌剂之应用 Download PDFInfo
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- CN1051994C CN1051994C CN95191948A CN95191948A CN1051994C CN 1051994 C CN1051994 C CN 1051994C CN 95191948 A CN95191948 A CN 95191948A CN 95191948 A CN95191948 A CN 95191948A CN 1051994 C CN1051994 C CN 1051994C
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- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- 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
- A01N43/04—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 with one hetero atom
- A01N43/14—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 with one hetero atom six-membered rings
- A01N43/16—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 with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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Abstract
通式(Ⅰ)异羟肟酸衍生物,在式中A代表氢或
一个易解离的基团,A1代表氢或烷基,Ar代表各任选取代的亚芳基或杂亚芳基,E代表1-链烯-1,1-双基-基团,它在2-位含有一个R1基,或代表一个2-氮杂-1-链烯-1,1-双基-基团,它在2-位含有一个R2基,或代表一个任选取代的亚氨基-基团(“氮杂亚甲基”,N-R3),G代表氧、代表各任选由卤素、羟基、烷基、卤代烷基或环烷基取代的链烷双基、链烯双基、链炔双基或一个下列的基团:
-Q-CQ-,-CQ-Q-,-CH2-Q-,-Q-CH2,-CQ-Q-CH2,-CH2-Q-CQ-.
-Q-CQ-CH2-,-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,-CH2-S(O)n-,-CQ-.
-S(O)n-CH2,-C(R4)=N-O-,-C(R4)=N-O-CH2-,-N(R5)-,-CQ-N(R5)-.
-N(R5)-CQ-,-Q-CQ-N(R5)-,-N=C(R4)-Q-CH2-,-CH2-O=N-C(R4)-.
-N(R5)-CQ-Q-,-CQ-N(R5)-CQ-Q-,或-N(R5)-CQ-Q-CH2-.
代表各任选取代的烷基、链烯基、链炔基、环烷基、芳基或杂环基,及其制备方法和作为杀真菌剂之应用。
Description
本发明涉及新的异羟肟酸衍生物,其制备方法和作为杀菌剂之应用。
若干异羟肟酸衍生物,例如:化合物N-羟基-α-肟基-呋咱-乙烷亚氨酸已经是人们熟悉的(参见Liebigs Ann.Chem.1975,1029~1050-引用在Chem.Abstracts 88:50732c)。然而这种化合物的生物性能还一无所知。
A代表氢或一个易解离的基团,
A1代表氢或烷基,
Ar代表各任选取代的亚芳基或杂亚芳基,
E代表1-链烯-1,1-双基-基团,它在2-位含有一个R1基,或代表一个2-氮杂-1-链烯-1,1-双基-基团,它在2-位含有一个R2基,或代表一个任选取代的亚氨基-基团(“氮杂亚甲基”,N-R3),其中
R1代表氢、卤素、氰基或各任选取代的烷基、烷氧基、烷硫基、烷氨基或二烷氨基,
R2代表氢、氨基、氰基或各任选取代的烷基、烷氧基、烷氨基或二烷氨基,和
R3代表氢、氰基或各任选取代的烷基、链烯基、链炔基、环烷基或环烷烷基,
G代表氧、各任选由卤素、羟基、烷基、卤代烷基或环烷基取代的链烷双基、链烯双基、链炔双基或一个下列的基团:
-Q-CQ--,-CQ-Q-,-CH2-Q-,-Q-CH2-,-CQ-Q-CH2-,-CH2-Q-CQ-,-Q-CQ-CH2-,
-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R4)=N-O-,
-C(R4)=N-O-CH2-,-N(R5)-,-CQ-N(R5)-,-N(R5)-CQ-,-Q-CQ-N(R5)-,
-N=C(R4)-Q-CH2-,-CH2-O=N-C(R4)-,-N(R5)-CQ-Q-,-CQ-N(R5)-CQ-Q-,或
-N(R5)-CQ-Q-CH2-,其中
n代表数字0、1或2,
Q代表氧或硫,
R4代表氢、氰基或各任选取代的烷基、烷氧基、烷硫基、烷氨基、二烷氨基或环烷基,
R5代表氢、羟基、氰基或各任选取代的烷基、烷氧基或环烷基,和
Z代表各任选取代的烷基、链烯基、链炔基、环烷基、芳基或杂环基。
另外发现,如果将通式(II)羧酸衍生物式中
Ar、E、G和Z具有上述含义,和
R代表氢或烷基,
与一个通式(III)的羟胺
A1-NH-O-A (III)式中
A和A1具有上述含义,
—或者与一个卤化氢的这类羟胺—
任选的在一种酸受体存在下和任选的在一种稀释剂的存在下进行反应,人们就可以得到通式(I)的新的异羟肟酸衍生物。
最后发现,该种新的通式(I)异羟肟酸衍生物显示非常强的杀菌作用。
本发明所述的化合物可以在一定条件下作为各种可能的异构形式的混合物,尤其是E-和Z-异构体,在一定条件下也以互变异构体存在。不仅需要E-异构体,而且需要Z-异构体,也需要这些异构体的任何的混合物,以及可能的互变异构形式。
本发明的对象首先是通式(I)化合物,式中
A代表氢、任选由卤素、氰基、羟基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷氧基、N,N-二-(C1-C4-烷基)-氨基、N-(C1-C4-烷基-羰基)-氨基、N-(C1-C4-烷基)-N-(C1-C4-烷基-羰基)-氨基、N-(C1-C4-烷氧基-羰基)-氨基或N-(C1-C4-烷基)-N-(C1-C4-烷氧基-羰基)-氨基取代的具有1至8个碳原子的烷基,代表C1-C4-烷氧基-羰基,代表C1-C4-烷氨基-羰基或二-(C1-C4-烷基)-氨基-羰基,
A1代表氢或具有1至6个碳原子的烷基,
Ar代表各任选取代的亚苯基或亚萘基或带有5或6元环的杂亚芳基,环成员中至少一个代表氧、硫或氮和任选的一个或2个以上代表氮,其中可能的取代基最好由下列的基团选取:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基,分别为直链的或支链的、分别带有1至6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基、分别为直链的或支链的、分别带有2至6个碳原子的链烯基、链烯氧基或链炔氧基,分别为直链的或支链的分别带有1至6个碳原子的和1至13个相同或不同的卤素原子的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,分别为直链的或支链的分别带有2至6个碳原子和1至13个相同或不同的卤原子的卤代链烯基或卤代链烯氧基,分别为直链或支链的在各烷基部分分别带有1至6个碳原子的烷氨基、二烷氨基、烷基羰基、烷基羰氧基、烷氧基羰基、烷基磺酰氧基、肟基烷基或烷肟基烷基,分别双重连结在一起、分别带有1至6个碳原子的链烯基或双氧链烯基,它们可分别由单一或多重的、相同或不同的卤素和/或直链或支链的带有1至4个碳原子的烷基和/或直链或支链的带有1至4个碳原子和1至9个相同的或不同的卤原子的卤代烷基任选取代,
E代表下列基团之一其中
R代表氢或带有1至6个碳原子的烷基,
R1代表氢、卤素、氰基或各任选由卤素、氰基或C1-C4-烷氧基取代的烷基、烷氧基、烷硫基、烷氨基或二烷氨基,其中烷基分别具有1至6个碳原子,
R2代表氢、氨基、氰基或各任选由卤素、氰基或C1-C4-烷氧基取代的烷基、烷氧基、烷氨基或二烷氨基,其中烷基分别具有1至6个碳原子,和
R3代表氢、氰基或各任选由卤素、氰基或C1-C4-烷氧基取代的含最多6个碳原子的烷基、链烯基或链炔基,或代表各任选由卤素、氰基、羧基、C1-C4-烷基或C1-C4-烷氧基-羰基等取代的环烷基或环烷基烷基,其中在环烷基部分中有3至6个碳原子,在烷基部分中任选有1至4个碳原子,
G代表氧、各任选由卤素、羟基、C1-C4-烷基、C1-C4-卤代烷基或C3-C6-环烷基等取代的含最多4个碳原子的链烷双基、链烯双基或链炔双基,或下列基团之一:
-Q-CQ-,-CQ-Q-,-CH2-Q-,-Q-CH2-,-CQ-Q-CH2-,-CH2-Q-CQ-,-Q-CQ-CH2-,
-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R4)=N-O-,
-C(R4)=N-O-CH2-,-N(R5)-,-CQ-N(R5)-,-N(R5)-CQ-,-Q-CQ-N(R5)-,
-N=C(R4)-Q-CH2-,-CH2-O-N=C(R4)-,-N(R5)-CQ-Q-,-CQ-N(R5)-CQ-Q-,或
-N(R5)-CQ-Q-CH2-,其中
n代表数字0、1或2,
Q代表氧或硫,
R4代表氢、氰基、任选由卤素、氰基或C1-C4-烷氧基等取代的烷基、烷氧基、烷硫基、烷氨基或二烷氨基,其中在烷基中分别有1至6个碳原子,或代表各任选由卤素、氰基、羧基、C1-C4-烷基或C1-C4-烷氧基-羰基等取代的具有3至6个碳原子的环烷基,
R5代表氢、羟基、氰基或代表任选由卤素、氰基或C1-C4-烷氧基等取代的具有1至6个碳原子的烷基或代表任选由卤素、氰基、羧基、C1-C4-烷基或C1-C4-烷氧基-羰基等取代的具有3至6个碳原子的环烷基,和
Z代表任选由卤素、氰基、羟基、氨基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(它们是各任选由卤素取代的)等取代的具有1至8个碳原子的烷基,代表各任选由卤素取代的分别具有最多为8个碳原子的链烯基或链炔基,代表各任选由卤素、氰基、羧基、苯基(它是任选由卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基等取代的)、C1-C4-烷基或C1-C4-烷氧基-羰基取代的具有3至6个碳原子的环烷基,代表各任选的取代的苯基、萘基或代表具有3至7元环的杂环基,其中杂原子至少有一个代表氧、硫、或氮和任选的一个或2个另外的杂原子代表氮,这里可能的取代基最好由以下列举的基团选取:
卤素、氰基、硝基、氨基、羟基、甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基、各个直链的或支链的烷基、烷氧基、烷硫基、烷基亚磺酰基或烷基磺酰基,其中烷基分别带有1至6个碳原子,各个直链的或支链的分别带有2至6个碳原子的链烯基或链烯氧基,各个直链的或支链的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基或卤代烷基磺酰基,其中烷基分别带有1至6个碳原子和1至13个相同或不同的卤素原子,各个直链的或支链的卤代链烯基或卤代链烯氧基,其中链烯基部分分别带有2至6个碳原子和1至13个相同的或不同的卤素原子,各个直链的或支链的烷氨基、二烷氨基、烷基羰基、烷基羰基氧基、烷氧基羰基、烷基磺酰基氧基、肟基烷基或烷肟基烷基,其中在单一的烷基部分里分别有1至6个碳原子,各个双重连结在一起的分别带有1至6个碳原子的链烯基或二氧链烯基,它们可分别由单一或多重的、相同或不同的卤素和/或直链或支链的具有1至4个碳原子的烷基和/或直链或支链的具有1至4个碳原子和1至9个相同或不同的卤素原子的卤代烷基任选取代,带有3至6个碳原子的环烷基,分别带有3至7元环的杂环基或杂环基甲基,其中在杂环里有1至3个相同或不同的杂原子—尤其氮、氧和/或硫—,以及各个在苯环上单一的或多重的,相同或不同的由卤素、氰基和/或直链或支链的具有1至4个碳原子的烷基和/或直链或支链的具有1至4个碳原子和1至9个相同或不同的卤原子的卤代烷基和/或直链或支链的具有1至4个碳原子的烷氧基和/或直链或支链的具有1至4个碳原子和1至9个相同或不同的卤原子的卤代烷氧基任选取代的苯基、苯氧基、苯甲基、苯甲氧基、苯乙基或苯乙氧基。
在定义中,饱和的或不饱和的烃链是如烷基、链烷双基、链烯基或链炔基,也与杂原子连结在一起,如烷氧基、烷硫基或烷氨基,分别为直链的或支链的。
卤素通常代表氟、氯、溴或碘,优选的为氟、氯或溴,尤其是氟或氯。
本发明尤其涉及通式(I)化合物,在式中
A代表氢、代表任选由氟、氯、甲氧基、乙氧基、正-或异丙氧基、甲氧基-乙氧基、乙氧基-乙氧基、二甲氨基、二乙氨基、乙酰氨基、丙酰氨基、N-甲基-乙酰氨基、N-乙基-乙酰氨基、N-甲基-丙酰氨基、N-乙基-丙酰氨基、甲氧基羰基氨基、乙氧基羰基氨基、N-甲基-N-甲氧基羰基氨基、N-乙基-N-甲氧基羰基氨基、N-甲基-N-乙氧基羰基氨基或N-乙基-N-乙氧基羰基氨基等取代的甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,代表甲氧基羰基、乙氧基羰基、甲氨基羰基、乙氨基羰基、二甲氨基羰基或二乙氨基羰基,
A1代表氢、甲基、乙基、正-或异丙基、正-、异-或仲丁基,
Ar代表各任选取代的邻-、间-或对位亚苯基,代表呋喃双基、噻吩双基、吡咯双基、吡唑双基、三唑双基、噁唑双基、异噁唑双基、噻唑双基、异噻唑双基、噁二唑双基、噻二唑双基、吡啶双基(尤其吡啶-2,3-双基)、嘧啶双基、哒嗪双基、吡嗪双基、1,3,4-三嗪双基或1,2,3-三嗪双基,其中可能的取代基尤其可以从下列列举的基团选取:
氟、氯、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、甲硫基、甲基亚磺酰基或甲基磺酰基,
E代表以下基团之一其中
R代表甲基、乙基、正-或异丙基、正-、异-或仲丁基,
R1代表氢、氟、氯、溴、氰基或代表各任选由氟、氯、氰基、甲氧基或乙氧基等取代的甲基、乙基、丙基、甲氧基、乙氧基、甲硫基、乙硫基、甲氨基、乙氨基或二甲氨基,
R2代表氢、氨基、氰基或代表各任选由氟、氯、氰基、甲氧基或乙氧基等取代的甲基、乙基、甲氧基、乙氧基、甲氨基、乙氨基或二甲氨基,和
R3代表氢、氰基或各任选由氟、氰基、甲氧基或乙氧基等取代的甲基、乙基、正-或异丙基、正-、异-或仲丁基、代表烯丙基或炔丙基或代表各任选由氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基-羰基或乙氧基-羰基等取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基,
G代表氧、代表各任选由氟、氯、羟基、甲基、乙基、正-或异丙基、三氟甲基、环丙基、环丁基、环戊基或环己基等取代的亚甲基、二亚甲基(乙烷-1,2-双基)、亚乙基-1,2-双基、乙炔-1,2-双基或者以下基团之一:
-Q-CQ--,-CQ-Q-,-CH2-Q-,-Q-CH2-,-CQ-Q-CH2-,-CH2-Q-CQ-,-Q-CQ-CH2-,
-Q-CQ-Q-CH2-,-N=N-,-S(O)n-,-CH2-S(O)n-,-CQ-,-S(O)n-CH2-,-C(R4)=N-O-,
-C(R4)=N-O-CH2-,-N(R5)-,-CQ-N(R5)-,-N(R5)-CQ-,-Q-CQ-N(R5)-,
-N=C(R4)-Q-CH2-,-CH2-O-N=C(R4)-,-N(R5)-CQ-Q-,-CQ-N(R5)-CQ-Q-,或
-N(R5)-CQ-Q-CH2-,其中
n代表数字0、1或2,
Q代表氧或硫,
R4代表氢、氰基、代表任选由氟、氯、氰基、甲氧基或乙氧基等取代的甲基、乙基、正-或异丙基、正-、异-或仲丁基、甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲氨基、乙氨基、丙氨基、二甲氨基或二乙氨基或代表各任选由氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基-羰基或乙氧基-羰基等取代的环丙基、环丁基、环戊基或环己基,
R5代表氢、羟基、氰基或代表各任选由氟、氯、氰基、甲氧基或乙氧基等取代的甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基或任选由氟、氯、氰基、羧基、甲基、乙基、正-或异丙基、甲氧基-羰基或乙氧基-羰基等取代的环丙基、环丁基、环戊基或环己基,和
Z代表任选由氟、氯、溴、氰基、羟基、氨基、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基(它们可以是各任选由氟和/或氯取代的)等取代的甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基,代表各任选由氟、氯或溴等取代的烯丙基、丁烯基、1-甲基-烯丙基、炔丙基或1-甲基-炔丙基,代表各任选由氟、氯、溴、氰基、羧基、苯基(它可以是任选由氟、氯、溴、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基或三氟甲氧基等取代的)、甲基、乙基、正-或异丙基、甲氧基-羰基或乙氧基-羰基等取代的环丙基、环丁基、环戊基或环己基,代表各任选取代的苯基、萘基、呋喃基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、环氧乙烷基、Oxetanyl、四氢呋喃基、全氢吡喃、吡咯烷基、哌啶基或吗啉基,其中可能的取代基最好选自下列基团:
氟、氯、溴、氰基、硝基、氨基、羟基甲酰基、羧基、氨基甲酰基、硫代氨基甲酰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氨基、乙氨基、正-或异丙氨基、二甲基氨基、二乙基氨基、乙酰基、丙酰基、乙酰氧基、甲氧基羰基、乙氧基羰基、甲基磺酰氧基、乙基磺酰氧基、肟甲基、肟乙基、甲肟甲基、乙肟甲基、甲肟乙基或乙肟乙基,各任选由单一或多重的,相同或不同的氟、氯、甲基、乙基、正-或异丙基、环丙基、环丁基、环戊基或环己基等取代的三亚甲基(丙烷-1,3-双基)、亚甲基双氧基或亚乙基双氧基,以及各在苯环上单一或多重的,相同或不同的由氟、氯、溴、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基或三氟甲氧基等任选取代的苯基、苯氧基、苯甲基或苯甲氧基。
一组特别优选的本发明所述的化合物是这样一类通式(I)化合物,在式中
A代表氢,
A1代表氢或甲基,
Ar代表邻亚苯基、吡啶-2,3-双基或噻吩-2,3-双基,
R1和R2分别代表甲氧基,
G代表氧、亚甲基或下列基团之一:
-CH2-O-,-O-CH2-,-S(O)n-,-CH2-S(O)n-,-S(O)n-CH2-,-C(R4)=N-O-,
-O-N=C(R4)-,-C(R4)=N-O-CH2-,-N(R5)-或-CH2-O-N=C(R4)-,其中
n代表数字0、1或2,
R4代表氢、甲基或乙基,
R5代表氢、甲基或乙基,和
Z代表各任选取代的苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基或1,3,5-三嗪基,其中可能的取代基最好选自以下基团:
氟、氯、溴、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧基羰基、乙氧基羰基、甲肟甲基、乙肟甲基、甲肟乙基或乙肟乙基,各任选单一或多重的,相同或不同的由氟、氯、甲基或乙基等取代的亚甲基双氧基或亚乙基双氧基,以及各任选在苯环上单一或多重的,相同或不同的由氟、氯、溴、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基或三氟甲氧基等取代的苯基、苯氧基、苯甲基或苯甲氧基。
上面举出的一般的或在优选部分规定的基团定义,不仅适合于通式(I)的最终产物,而且也适合于各制备过程所必需的原料及中间产物。
这些基团定义可以彼此之间,也可以在优选化合物的规定范围之间,任意的组合。
为了实施本发明所述的方法作为原料所必需的羧酸衍生物是通过通式(II)作一般定义的。在这个通式(II)中,Ar、E、G和Z其优选的和特别的含义,在描述通式(I)化合物时,作为优选的和特别优选的Ar、E、G和Z已经作了规定。R优选的代表具有1至4个碳原子的烷基,特别优选的代表甲基或乙基。
通式(II)原材料是已知的和/或可以根据已知的方法进行制备(参见EP-A 178826,EP-A 242081,EP-A 382375,EP-A493711)。
另一个作为原料使用的羟胺是通过通式(III)作一般定义的。在通式(III)中,A优选的及特别优选的含义,已经在描述通式(I)化合物时,作为优选的及特别优选的对A作了规定。
通式(III)原料是已知的有机合成化学试剂。
本发明所述的方法最好在一种适宜的酸受体存在下进行。作为这类受体,所有的普通的无机或有机碱都可以考虑。属于这类的例如有碱土金属-或碱金属氢化物、-氢氧化物、-氨化物、-醇化物、-乙酸盐、-碳酸盐或碳酸氢盐,例如:氢化钠、氨基钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、醋酸钠、醋酸钾、醋酸钙、醋酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基-苯甲胺、吡啶、N-甲基哌啶基、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBu)。
作为实施本发明所述方法的稀释剂可以考虑水和有机溶剂。属于此类的尤其是脂肪族、脂环族或芳香族,任选卤化的烃类,例如:汽油、苯、甲苯、二甲苯、氯代苯、二氯代苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚:如二乙醚、二异丙醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮类:如丙酮、丁酮或甲基-异丁基-酮;腈类:如乙腈、丙腈或苄腈;酰胺类:如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酸三胺;酯类:如醋酸甲酯或醋酸乙酯;亚砜类:如二甲基亚砜;醇类:如甲醇、乙醇、正-或异丙醇、乙二醇单甲醚、乙二醇单乙醚、二甘醇单甲醚、二甘醇单乙醚、它们与水的混合物或者纯净水。
反应温度在实施本发明所述方法时可以在一个很宽的范围里变动。通常工作温度在-20℃和+100℃之间,优选的在0℃和50℃之间。
为了实施本发明所述的方法,对每一个摩尔通式(II)羧酸衍生物通常投入1至5摩尔,优选的1至2.5摩尔羟胺或羟胺-卤氢酸盐和必要时投入1至10摩尔,优选的1至5摩尔酸受体。
反应的实施,反应产物的后处理和分离可按已知的方法进行(参见制备实施例)。
本发明所述的活性物质具有很强的杀灭微生物作用,并可以投入实用杀灭不受欢迎的微生物。活性物质用作植物保护剂,尤其适于作杀菌剂。
在植物保护中,本杀菌剂可用来杀灭根肿病菌纲、卵菌纲、弧菌纲、接合菌亚纲、子囊菌纲、担子菌纲和半知菌纲的微生物。
下述以非限定的方式列举了上述系统命名下的一些真菌病害的致病微生物:
腐霉属,例如:甘薯斑腐病;
疫病属,例如:马铃薯晚疫病;
假霜霉属,例如:律草假霜霉或生姜腐败病;
单轴霉属,例如:葡萄霜霉病;
霜霉菌属,例如:Peronospora pisi或大白菜霜霉病;
白粉菌属,例如:葫芦白粉病;
球壳菌属,例如:黄瓜白粉病;
足球菌属,例如:苹果白粉病;
黑星菌属,例如:苹果黑星病;
Pyrenophora属,例如:大麦网斑病或大麦条纹病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
旋孢霉素属,例如:稻胡麻斑病(分生孢子型:眼斑点病。同物异名:大麦网斑霉);
单孢锈菌属,例如:菜豆锈病;
双孢锈菌属,例如:小麦叶锈病;
腥黑粉菌属,例如:小麦网腥黑穗病;
黑粉菌属,例如:Ustilago nuda或燕麦散黑穗病;
薄膜霉属,例如:稻纹枯病;
梨孢霉属,例如:稻瘟病;
镰刀霉属,例如:禾杆镰孢菌;
葡萄孢属,例如:灰葡萄孢;
壳针孢霉属,例如:小麦颍枯病;
细球壳菌属,例如:小麦白叶斑病;
尾孢霉属,例如:小豆褐斑病;
交链孢属,例如:甘蓝黑斑病和
葡萄假尾孢霉属,例如:Pseudocercosporella herpotrichoides。
植物对消灭植物病害所需浓度的活性化合物的良好的耐受性,使得用其处理植物的地上部分、植物的繁殖原种和种子,以及植物生长的土壤成为可能。
在本文中,使用根据本发明的活性化合物防治果树和蔬菜栽培中的病害,如疫霉属和黑星菌属的病害、或防治谷物病害,如白粉菌属的病害、以及防治水稻病害,如稻瘟病有特别高水平的效果。
在防治植物病害所需的浓度条件下,活性物质有很好的植物相容性,这一相容性允许对地面上的植物部分、植物的块茎和种子以及土壤进行处理。
本发明所述的活性物质用于防治水果栽培和蔬菜种植中的病害有特别好的结果,例如对Phytophthora-和Venturia-类别,或防治谷物病害,例如对Erysiphe-类别,以及防治水稻病害,例如对Pyricularia Oryzae。
活性物质可以根据它的物理和/或化学特性转化成常用的供药形式,如溶液、乳浊液、悬浮液、粉末、泡沫、药膏、颗粒、气溶胶、聚合物的微胶囊和种子的包裹物,以及ULV-冷的-和ULV-热的雾化形式。
这些供药形式可以用已知的方法进行制备,例如:通过活性物质与增充剂相混合,增充剂就是液体的溶剂、在压力下液化的气体和/或固体的载体材料,必要时使用表面活性剂,也就是乳化剂和/或分散剂和/或泡沫生成剂。在使用水作为增充剂时,可以用有机溶剂作为助溶剂。作为液体的溶剂一般可以考虑用芳香族化合物,如二甲苯、甲苯、烷基萘、氯代芳香化合物或氯代脂肪烃类,如氯苯、氯乙烯或二氯甲烷,脂肪烃类,如环己烷或石蜡,例如:石油馏份,醇类,如丁醇或甘醇以及它们的醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性的溶剂,如二甲基甲酰胺或二甲基亚砜,以及水,液化气体增充剂或载体是这样一种液体,它在常温常压下是气体,例如:气溶胶的膨胀气体,如卤代烃类以及丁烷、丙烷、氮气和二氧化碳;作为固体载体可以考虑用:例如天然的岩石粉,如陶土、矾土、滑石粉、白垩、石英粉、一种美国活性白土(Attapulgit)、高岭石或硅藻土(Diatomeenerde)和人工合成的岩石粉,如高度分散的硅酸、氧化铝和硅酸盐;作为固体的颗粒载体材料可以考虑用:例如粉碎和分级的天然岩石,如方解石、大理石、浮石、海泡石、白云石以及由无机和有机粉末人工合成的颗粒,以及由有机材料合成的颗粒,如锯末、椰子壳、玉米芯轴和烟草梗;作为乳化剂和/或泡沫发生剂可以考虑用,例如非离子型和阴离子型乳化剂,如聚氧乙烯-脂肪酸酯、聚氧乙烯-脂肪醇醚,例如烷芳基聚甘醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白水解产物;作为分散剂可以考虑用,例如木素亚硫酸盐废碱液和甲基纤维素。
在剂型中作为胶粘剂可以使用羧甲基纤维素、天然的和合成的,粉末状的、粒状的或胶乳状的聚合物,如阿拉伯胶、聚乙烯醇、聚醋酸乙烯酯,以及天然的磷脂,如脑磷脂和卵磷脂以及合成的磷脂。其它的添加物可以是矿物油和植物油。
着色剂可以用无机的颜料,例如氧化铁、氧化钛、亚铁氰兰和有机的染料,如茜素-、偶氮-和金属酞氰染料和痕量养料,如铁、锰、硼、铜、钴、钼和锌等盐类。
制剂通常含有活性物质在0.1和95%重量之间,优选的在0.5和90%之间。
本发明所述的活性物质可以单独使用,或者以它的供药形式与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂混合使用,以便扩大有效范围或防止抗药性的发展。在多数情况下出现协同效应。
用于混合的药剂可以考虑以下的例子:
杀真菌剂:
2-氨基丁烷、2-苯胺基-4-甲基-6-环丙基-嘧啶;2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-甲氧亚氨基-N-甲基-2-(2-苯氧苯基)乙酰胺;8-羟基喹啉硫酸盐;甲基-(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧]-苯基}-3-甲氧丙烯酸酯;甲基-(E)-甲氧亚氨基[α-(对甲苯氧基)-对甲苯基]乙酸酯;2-苯基苯酚(OPP),艾敌吗啉,Ampropylfos,敌菌灵,戊环唑,苯霜灵,麦锈灵,苯菌灵,Binapacryl,联苯酚,双苯三唑醇,灭瘟素,乙嘧酚磺酸酯,糠菌唑,粉病定,
多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌利,硫杂灵,霜脲氨,环唑醇,酯菌氨,
双氯酚,苄氯三唑醇,苯氟磺胺,达菌清,氯硝胺,乙霉威,恶醚唑,甲菌定,烯酰吗啉,烯唑醇,低螨普,二苯胺,Dipyrithion,灭菌磷,二嗪农,多果定,敌菌酮,
克瘟散,Epoxyconazole,乙菌克,氯唑灵,
异嘧菌醇,Fenbuconazole,呋菌胺,种衣醇,拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,Fludioxonil,氟菌安,Fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋氨丙灵,拌种胺,
双胍盐,
氯苯嘧啶醇,己唑醇,土消菌,
烯菌灵,酰胺唑,双胍辛醋酸盐,Iprobenfos,(IBP),异丙定,富士一号,
春雷霉素,铜制备物:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多混合物,
锰铜混剂,代森锰锌,代森锰,嘧菌胺,灭锈胺,瑞毒霉,Metconazol,磺菌威,甲呋菌胺,代森联,嘧菌胺,氰菌唑,
福美镍,异丙消,环菌灵,
甲呋酰胺,恶霜灵,Oxamocarb,氧化萎锈灵,
稻瘟酯,戊菌唑,戊醇隆,Phosdiphen,多马霉素,粉病灵,多氧霉素,噻菌灵,并氯灵,杀菌利,百维灵,丙环唑,甲基代森锌,定菌磷,啶斑肟,Pyrimethanil,毛醌素,
五氯硝基苯(PCNB),
硫和硫制备物,
戊唑醇,白叶减,四氯硝基苯,氟醚唑,涕必灵,噻菌腈,甲基托布津,福美双,甲基立枯磷,对甲抑菌灵,唑菌酮,唑菌醇,唑菌嗪,杨菌胺,三环唑,克啉菌,氟菌唑,嗪氨灵,Triticonazol,
有效霉素,烯菌酮,
代森锌,福美锌。
杀细菌剂
溴硝丙二醇,双氯酚,氯定,福美镍,春雷霉素,Octhilinone,呋喃甲酸,氧化萎锈灵,噻菌灵,链霉素,白叶减,硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素(abamectin),AC 303 630,乙酰甲胺磷,氟硝菊酯,棉铃威,涕灭威,甲体氯氰菊酯,虫螨脒,齐墩螨素(avermectin),AZ60541,azadirachtin,谷硫磷,乙基谷硫磷,唑环锡,
苏云菌杆菌,恶虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,丁苯威,溴硫磷,全杀威,噻嗪酮,丁叉威,达螨酮,
硫线磷,西维因,呋喃丹,三硫磷,丁硫克百威,杀螟丹,CGA157419,CGA 184699,chloethocarb,chlorethoxyfos,chloretoxyfos,毒虫威,定虫隆,氯甲磷,毒死蜱,甲基毒死蜱,顺-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,β-氟氯氰菊酯,三氟氯氰菊酯,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,甲基内吸磷,甲基内吸磷S赶式异构体,内吸磷,杀螨隆,二嗪农,除线磷,敌敌畏,Dicliphos,百治磷,乙硫磷,氟脲杀,乐果,甲基毒虫畏,敌杀磷,乙拌磷,
克瘟散,Emamectin,高氰戊菊酯,苯虫威,乙硫磷,醚菊酯(ethofenprox),ethoprophos,etofenprox,氯嘧啶磷,
克酰磷,喹螨醚,杀螨锡,杀螟松,fenobucarb,苯硫威,双氧威,分扑菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,
fipronil,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫磷,安果,噻唑硫磷,fubfenprox,呋线威,
六六六,庚虫磷,氟铃脲,噻螨酮,
咪蚜胺,iprobenfos,异唑磷,丙胺磷,异丙威,异噁唑磷,齐墩螨素(ivemectin),α-三氟氯氰菊酯,Iufenuron,
马拉硫磷,灭蚜磷,mervinphos,甲丙硫磷,多聚甲醛,虫螨畏,甲胺磷,杀扑磷,灭虫威,灭多威,metolcarb,milbemectin,久效磷,moxidectin,
二溴磷,NC 184,NI 25,nitenpyram,
氧化乐果,甲叉丙威,砜吸磷,oxydeprofos,
对硫磷,甲基对硫磷,氯菊酯,稻丰散,甲拌磷,伏杀磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,虫螨磷,乙基虫螨磷,溴丙磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,哒嗪硫磷,反灭菊酯,除虫菊,哒嗪酮,pyrimidifen,蚊蝇醚,喹硫磷,
RH 5992,
杀抗松,克线丹,silafluofen,治螟磷,乙丙硫磷,
tebufenozide,tebufenpyrad,teburimimphos,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫威,thiafenox,硫双灭多威,特氨叉威,甲基乙拌磷,治线磷,苏云菌杆菌,四溴菊酯,triarathen,三唑磷,trizuron,敌百虫,triflumuron,三叉威,
蚜灭多,二甲威,xylylcarb,YI5301/5302,zetamethrin。
与其它已知的活性物质,如除莠剂或与肥料和生长调节剂相混合也是可能的。
活性物质可以单独使用,也可以制剂形式或由此配制的使用形式被使用,如已备好的可供使用的溶液、悬浮液、喷粉、药膏、溶解的粉末、细粉剂和颗粒。
应用采取常用的方式,例如:通过浇、喷射、喷洒、撒落、使之雾化、使之成泡沫、涂抹等等。另外可以按超小体积方法将活性物质生产出来或将活性物质制剂或活性物质本身注入土壤中。也可以处理植物的种子。
在处理植物部分时,活性物质的浓度在使用形式中可以在一个很宽的范围里变动。通常在1和0.0001%重量之间,优选的在0.5和0.001%重量之间。
在处理种子时,通常每一公斤种子用0.001至50g活性物质,优选的为0.01至10g。
在处理土壤时,在有效地点的活性物质浓度要求由0.00001至0.1%重量,优选由0.0001至0.02%重量。
将2.67g(38.4mmol)盐酸胲事先置于40ml甲醇中,并在10℃将6.0g(19.2mmol)α-甲肟基-α-[2-(2-甲基-苯氧基-甲基)-苯基]-醋酸甲酯分成几分加入其中。然后在冰浴冷却下将13.8g一种30%的甲醇钠溶液(76.8mmol NaOCH3)在15分钟之内滴加到混合物中,随后撤掉冰浴,让反应混合物在0℃至20℃搅拌3小时。
为了后处理,将沉积物搅入稀盐酸中(由6ml浓盐酸和100g冰水组成),然后用醋酸乙酯提取,有机相用硫酸钠干燥并过滤。将溶剂从滤液中用真空水泵仔细的蒸掉。
得到5.3g(81%理论值)α-甲肟基-α-[2-(2-甲基-苯氧甲基)-苯基]-乙酰异羟肟酸(根据“液体色谱法”,纯度为92%),其熔点为65℃。
1H-NMR(D6-二甲基亚砜,δ):2.20,3.88,3.95,6.8-7.55,9.2ppm。
类似实施例1以及本发明所述的制备方法一般的描述相应地可以制备出下面表1中列出的通式(I)化合物。
1H-NMR-谱图的记录是在CDCl3中或在D6-二甲基亚砜中用四甲基硅烷作为内标。通常以δ-值表述化学位移。
表1:通式(I)化合物的实施例实施例 Z G Ar E A A1 物理数据序号实施例 z G Al E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号实施例 Z G Ar E A A1 物理数据序号应用实施例实施例A
Pyricularia-试验(水稻)/防护的
溶剂:12.5重量份丙酮
乳化剂:0.3重量份烷芳基聚甘醇醚
为了制备一种合乎目的的活性物质制剂,人们将1重量份的活性物质与规定量的溶剂相混合,并且用水和规定量的乳化剂稀释该浓缩液达到所需的浓度。
为了检验防护效果,人们用活性物质制剂喷水稻幼苗,直到湿淋淋的。当喷的涂层变干以后,给植物用一种Pyricularia Oryzao的孢子悬浮水溶液进行接种。随后将植物放入一个相对湿度为100%的25℃的温室中。
接种4天后评价疾病的侵袭情况。
在该试验中,例如根据制备实施例1的化合物,在活性物质浓度为0.025%时有效率为100%。实施例B
Pyricularia-试验(水稻)/系统的
溶剂:12.5重量份丙酮
乳化剂:0.3重量份烷芳基聚甘醇醚
为了制备一种合乎目的的活性物质制剂,人们将1重量份的活性物质与规定量的溶剂相混合,并且用水和规定量的乳化剂把浓缩物冲稀到所需的浓度。
为了检验系统性能,将40ml活性物质制剂浇入单位面积土壤中,在该土壤中插栽水稻幼苗。处理完七天过后,将水稻用一种PyriculariaOryzao孢子水悬浮液进行接种。随后让植物在一个相对湿度为100%的25℃的温室中呆到评价完毕。
接种4天后评价病害侵袭情况。
在这个试验中,例如根据制备实施例1的化合物,在使用量为每100cm2用100mg时,有效率为67%。实施例C
疫霉属(phytophthora)-试验(番茄)/防护的
溶剂:12.5重量份丙酮
乳化剂:0.3重量份烷芳基聚甘醇醚
为了制备一种合乎目的的活性物质制剂,人们将1重量份的活性物质与规定量的溶剂和乳化剂相混合,并且用水将浓缩物冲稀到所需的浓度。
为了检验防护效果,人们用活性物质喷洒植物幼苗,直到湿淋淋的。当喷洒涂层变干以后,将植物用一种蔓延疫霉孢子水悬浮液进行接种。
植物被放到一个相对湿度为100%的大约20℃的温室内。
接种3天后进行评价。
在这个试验中,例如根据制备实施例1的化合物,在活性物质浓度为0.025%时,有效率为67%。实施例D
白粉菌属(Erysiphe)-试验(大麦)/防护
溶剂:12.5重量份N-甲基-吡咯烷酮
乳化剂:0.3重量份烷芳基聚甘醇醚
为了制备一种合乎目的的活性物质制剂,人们将1重量份的活性物质与规定量的溶剂和乳化剂相混合,并且用水将浓缩物冲稀到所需的浓度。
为了检验防护效果,人们用活性物质制剂喷洒植物幼苗,使之淋湿。当喷洒涂层变干以后,用禾白粉菌f.sp.hordei孢子给植物授粉。
将植物放在一个相对湿度为大约80%的,温度为大约20℃的温室内。
接种7天后进行评价。
在这个试验中,例如根据制备实施例1的化合物,在活性物质浓度为0.025%时,有效率为89%。实施例E
黑星菌属(Venturia)-试验(苹果)/防护的
溶剂:12.5重量份丙酮
乳化剂:0.3重量份烷芳基聚甘醇醚
为了制备一种合乎目的的活性物质制剂,人们将1重量份的活性物质与规定量的溶剂和乳化剂相混合,并且用水冲稀该浓缩物达到所需浓度。
为了检验防护效果,人们用活性物质制剂喷植物幼苗,直到湿淋淋的。当喷洒涂层变干之后,用一种苹果黑星病苹果黑星菌(Venturiainaequalis)的分生孢子悬浮水溶液接种植物,然后在20℃和100%相对湿度下在恒温箱中放置1天。
接种后12天进行评价。
在这个试验中,例如根据制备实施例1的化合物,在活性物质浓度为0.025%时,有效率为100%。
Claims (5)
式中
A代表氢,
A1代表氢或甲基,
Ar代表邻亚苯基、吡啶-2,3-双基或噻吩-2,3-双基,
R1和R2分别代表甲氧基,
G代表氧、亚甲基或下列基团之一:
-CH2-O-,-O-CH2-,-S(O)n-,-CH2-S(O)n-,-S(O)n-CH2-,-C(R4)=N-O--O-N=C(R4)-,
-C(R4)=N-O-CH2-,-N(R5)-或-CH2-O-N=C(R4)-其中
n代表数字0、1或2,
R4代表氢、甲基、乙基或氰基,
R5代表氢、甲基或乙基,和
Z代表各任选取代的苯基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基或1,3,5-三嗪基或噻二唑基,其中取代基选自以下基团:
氟、氯、溴、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正-或异丙氧基、甲硫基、乙硫基、正-或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基、甲氧基羰基、乙氧基羰基、甲肟甲基、乙肟甲基、甲肟乙基或乙肟乙基,各自被相同或不同的氟、氯、甲基或乙基任选取代一次或多次的亚甲基双氧基或亚乙基双氧基,以及各在苯环上被相同或不同的氟、氯、溴、氰基、甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、甲氧基、乙氧基、正-或异丙氧基、二氟甲氧基或三氟甲氧基任选取代一次或多次的苯基、苯氧基、苯甲基或苯甲氧基,吡啶、噻吩、苄硫基、1-丙烯基、硝基、苯氧基、苯基和被C1-4烷基、卤素、C1-C4卤代烷氧基或C1-C4卤代烷基取代的苯基。
2.害虫防治剂,其特征是它含有至少一种权利要求1所述的通式(I)化合物以及常规载体。
3.防治害虫的方法,其特征是,人们将权利要求1所述的通式(I)化合物作用于害虫和/或作用于它们的生存空间。
4.权利要求1所述的通式(I)化合物在用于防治害虫方面的应用。
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DEP4402533.5 | 1994-01-28 | ||
DE4402533A DE4402533A1 (de) | 1994-01-28 | 1994-01-28 | Hydroxamsäurederivate |
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US (1) | US6235790B1 (zh) |
EP (1) | EP0741695B1 (zh) |
JP (1) | JPH09508132A (zh) |
CN (1) | CN1051994C (zh) |
AU (1) | AU1534595A (zh) |
BR (1) | BR9506663A (zh) |
CA (1) | CA2182096A1 (zh) |
CZ (1) | CZ220696A3 (zh) |
DE (2) | DE4402533A1 (zh) |
ES (1) | ES2140655T3 (zh) |
HU (1) | HUT75607A (zh) |
PL (1) | PL315669A1 (zh) |
PT (1) | PT741695E (zh) |
WO (1) | WO1995020570A1 (zh) |
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DE19955130A1 (de) * | 1999-11-17 | 2001-05-23 | Bayer Ag | Hydroxamsäurederivate |
KR20060036567A (ko) * | 2004-10-26 | 2006-05-02 | 한기종 | 디포스젠을 이용한 하이드록사메이트 제조방법 |
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EP0463488A1 (de) * | 1990-06-27 | 1992-01-02 | BASF Aktiengesellschaft | O-Benzyl-Oximether und diese Verbindungen enthaltende Pflanzenschutzmittel |
EP0579124A1 (de) * | 1992-07-15 | 1994-01-19 | BASF Aktiengesellschaft | Substituierte Oximether, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen und Pilzen |
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US3823161A (en) * | 1970-05-07 | 1974-07-09 | Exxon Research Engineering Co | Aminothiophene derivatives |
DE4030038A1 (de) | 1990-09-22 | 1992-03-26 | Basf Ag | Ortho-substituierte phenylessigsaeureamide |
US6008257A (en) * | 1994-01-28 | 1999-12-28 | Bayer Aktiengesellschaft | Hydroxamic-acid derivatives, method of preparing them and their use as fungicides |
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1994
- 1994-01-28 DE DE4402533A patent/DE4402533A1/de not_active Withdrawn
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1995
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- 1995-01-16 PT PT95906953T patent/PT741695E/pt unknown
- 1995-01-16 JP JP7519859A patent/JPH09508132A/ja not_active Ceased
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- 1995-01-16 ES ES95906953T patent/ES2140655T3/es not_active Expired - Lifetime
- 1995-01-16 CN CN95191948A patent/CN1051994C/zh not_active Expired - Fee Related
- 1995-01-16 HU HU9602045A patent/HUT75607A/hu unknown
- 1995-01-16 AU AU15345/95A patent/AU1534595A/en not_active Abandoned
- 1995-01-16 BR BR9506663A patent/BR9506663A/pt not_active Application Discontinuation
- 1995-01-16 PL PL95315669A patent/PL315669A1/xx unknown
- 1995-01-16 CA CA002182096A patent/CA2182096A1/en not_active Abandoned
- 1995-01-16 DE DE59507248T patent/DE59507248D1/de not_active Expired - Fee Related
- 1995-01-16 WO PCT/EP1995/000149 patent/WO1995020570A1/de active IP Right Grant
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0463488A1 (de) * | 1990-06-27 | 1992-01-02 | BASF Aktiengesellschaft | O-Benzyl-Oximether und diese Verbindungen enthaltende Pflanzenschutzmittel |
EP0579124A1 (de) * | 1992-07-15 | 1994-01-19 | BASF Aktiengesellschaft | Substituierte Oximether, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen und Pilzen |
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Publication number | Publication date |
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DE59507248D1 (de) | 1999-12-23 |
AU1534595A (en) | 1995-08-15 |
CN1143360A (zh) | 1997-02-19 |
PL315669A1 (en) | 1996-11-25 |
EP0741695A1 (de) | 1996-11-13 |
WO1995020570A1 (de) | 1995-08-03 |
HUT75607A (en) | 1997-05-28 |
DE4402533A1 (de) | 1995-08-03 |
HU9602045D0 (en) | 1996-09-30 |
US6235790B1 (en) | 2001-05-22 |
BR9506663A (pt) | 1997-09-16 |
PT741695E (pt) | 2000-04-28 |
JPH09508132A (ja) | 1997-08-19 |
EP0741695B1 (de) | 1999-11-17 |
CA2182096A1 (en) | 1995-08-03 |
CZ220696A3 (en) | 1996-11-13 |
ES2140655T3 (es) | 2000-03-01 |
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