CN1229368C - 用作农药和除草剂的苯基取代的5,6-二氢-吡喃酮-衍生物 - Google Patents
用作农药和除草剂的苯基取代的5,6-二氢-吡喃酮-衍生物 Download PDFInfo
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- CN1229368C CN1229368C CNB018129773A CN01812977A CN1229368C CN 1229368 C CN1229368 C CN 1229368C CN B018129773 A CNB018129773 A CN B018129773A CN 01812977 A CN01812977 A CN 01812977A CN 1229368 C CN1229368 C CN 1229368C
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- -1 Phenyl-substituted 5,6-dihydropyrone Chemical class 0.000 title claims abstract description 162
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 239000000575 pesticide Substances 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 107
- 238000002360 preparation method Methods 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims description 219
- 239000000460 chlorine Substances 0.000 claims description 106
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 90
- 239000001257 hydrogen Substances 0.000 claims description 90
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 80
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 79
- 229910052794 bromium Inorganic materials 0.000 claims description 79
- 239000011737 fluorine Substances 0.000 claims description 78
- 229910052731 fluorine Inorganic materials 0.000 claims description 78
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 239000002904 solvent Substances 0.000 claims description 66
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- 229910052736 halogen Inorganic materials 0.000 claims description 51
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
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- 241000607479 Yersinia pestis Species 0.000 claims description 9
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 2
- NTTSSAONTDQRAV-UHFFFAOYSA-N CCC([O])=O Chemical compound CCC([O])=O NTTSSAONTDQRAV-UHFFFAOYSA-N 0.000 claims description 2
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 claims description 2
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
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- 239000000463 material Substances 0.000 description 36
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 31
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- 125000004432 carbon atom Chemical group C* 0.000 description 16
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- 239000011787 zinc oxide Substances 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明涉及式(I)的新的苯基取代的5,6二氢吡喃酮衍生物,其中W、X、Y、Z、G、A、B、Q1、Q2具有说明书中指明的含义。本发明还涉及制备所述衍生物的几种方法及其作为杀虫剂和除草剂的用途。
Description
本发明涉及新的苯基取代的5,6-二氢-吡喃酮-衍生物、其多种制备方法及其用作农药和除草剂的用途。
已知,某些5,6-二氢吡喃酮-衍生物作为蛋白酶抑制剂具有抗病毒性能:WO 95/14012。此外,由Kawalakton衍生物合成4-苯基-6-(2-苯乙基)-5,6-二氢吡喃酮是已知的:Kappe等;Arch.Pharm.309,558-64,(1976)。此外5,6-二氢吡喃酮-衍生物作为中间体是已知的:White,J.D.,Brenner,J.B.,Deinsdale,M.J.,J.Amer.Chem.Soc.93,281-2(1971)。至今没有描述过在植物保护中的应用。
本发明提供新的式(I)化合物
其中
W表示氢、烷基、链烯基、链炔基、卤素、卤代烷基或烷氧基,
X表示卤素、烷基、烷氧基、链烯基、链炔基、卤代烷基、卤代烷氧基、氰基或各自任选取代的苯基、苯氧基、苯硫基、苯基烷氧基或苯基烷基硫基,
Y表示氢、烷基、卤素、卤代烷基、烷氧基、链烯基、链炔基或任选取代的芳基或杂芳基,
Z表示氢、卤素、烷基、烷氧基、卤代烷基、卤代烷氧基或氰基,
A表示一条键、氢、各自任选被卤素取代的烷基、链烯基、烷氧基烷基、任选取代的环烷基或环烷基烷基,其中任选至少一个环原子被杂原子替代,或各自任选被卤素、烷基、卤代烷基、烷氧基、卤代烷氧基、氰基或硝基取代的芳基、芳基烷基、杂芳基或杂芳基烷基,
B表示氢或烷基,或
A和B和与其相连的碳原子一起表示饱和或不饱和、任选含有至少一个杂原子的未取代的或取代的环,或
B和Q1一起表示各自任选被各自任选取代的烷基或烷氧基取代的链烷二基,其中两个不直接相邻的碳原子任选形成另一任选取代的环,或
Q1表示氢、羟基、烷基、烷氧基、烷氧基烷基、烷基酰基氧基、任选取代的环烷基(其中任选一个亚甲基被氧或硫代替)或任选取代的苯基,
Q2表示氢或烷基,或
Q1和Q2和与其连接的碳原子一起表示任选含有一个杂原子的未取代的或取代的环,
G表示氢(a)或下列基团之一
E(f)或
其中
E表示金属离子或铵离子,
L表示氧或硫,
M表示氧或硫,
R1表示各自任选被卤素取代的烷基、链烯基、烷氧基烷基、烷基硫基烷基、多烷氧基烷基或任选被卤素、烷基或烷氧基取代的环烷基,其中一个或多个亚甲基可被杂原子代替、各自任选取代的苯基、苯基烷基、杂芳基、苯氧基烷基或杂芳基氧基烷基,
R2表示各自任选被卤素取代的烷基、链烯基、烷氧基烷基、多烷氧基烷基或表示各自任选取代的环烷基、苯基或苄基
R3、R4和R5各自独立表示各自任选被卤素取代的烷基、烷氧基、烷基氨基、二烷基氨基、烷基硫基、链烯基硫基、环烷基硫基和表示各自任选取代的苯基、苄基、苯氧基或苯硫基,和
R6和R7各自独立表示氢、各自任选被卤素取代的烷基、环烷基、链烯基、烷氧基、烷氧基烷基、表示任选取代的苯基、表示任选取代的苄基,或与其连接的N原子一起表示任选被氧或硫间隔的环。
式(I)化合物尤其依据取代基的类型也可以几何和/或光学异构体或不同组成的异构体混合物存在,其可任选按常规方式和方法分离。本发明提供这些纯的异构体和其异构体混合物、其制备和用途以及含有它们的组合物。下面为了简单起见只称为式(I)化合物,但它们既意指其纯的异构体也指其具有不同异构体化合物含量的混合物。
依据取代基G的位置,式(I)化合物可存在式(I-A)和(I-B)两种异构体形式,
这通过式(I)中的虚线表示。
式(I-A)和(I-B)化合物可以混合物,也可以其纯的异构体形式存在。式(I-A)和(I-B)化合物的混合物可按已知方式通过物理方法,例如通过色谱法分离。
为了更清楚起见,在下面各种情况下只提及一种可能的异构体,这并不排除这些化合物可以任选以异构体混合物或各种情况下的另一异构体形式存在。
在基团G的各种含义(a)、(b)、(c)、(d)、(e)、(f)和(g)中得出下列主要结构(I-a)至(I-g)
其中
A、B、E、L、M、Q1、Q2、W、X、Y、Z、R1、R2、R3、R4、R5、R6和R7具有上述含义.
此外,已发现新的式(I)化合物可按下列方法之一获得:
(A)式(I-a)取代的5,6-二氢吡喃酮
其中
A、B、Q1、Q2、W、X、Y和Z具有上述含义,
可通过式(II)的O-酰基羟基羧酸酯
其中
A、B、Q1、Q2、W、X、Y和Z具有上述含义,和
R8表示烷基(优选C1-C6-烷基),
在溶剂存在下和在碱存在下进行分子内缩合得到。
此外,已发现,
(B)上述式(I-a)至(I-g)化合物,其中A、B、G、Q1、Q2、W、X、Y和Z具有上述含义,可通过如下得到:
式(I-a′)至(I-g′)化合物
其中
A、B、R1、R2、R3、R4、R5、R6、R7、E、L、M、Q1、Q2、W′、X′、Y′和Z′具有上述W、X、Y和Z的含义并且其中基团W′、X′、Y′至少一个表示氯、溴或碘,优选表示溴,
并且Z′不表示溴或碘,
α)与式(III)的硅烷基乙炔
其中
R9表示氢,和
R10表示C1-C4-烷基或苯基,特别是表示甲基或叔丁基,首先在溶剂、碱和催化剂存在下反应,其中合适的催化剂特别是钯络合物,并随后除去硅烷基,
或
β)与式(IV)的乙烯基锡烷
其中
R9表示氢、甲基或乙基,和
R10表示C1-C4-烷基,尤其是丁基,
在溶剂、碱和催化剂存在下反应,其中合适的催化剂特别是钯络合物,或
γ)在特殊情况下,如果Y′表示氯、溴或碘,优选表示溴,和W′、X′和Z′不表示溴或碘,与式(V)的硼酸
其中
Y表示任选取代的苯基或杂芳基,
在溶剂、碱和催化剂存在下反应,其中合适的催化剂特别是钯络合物。此外,已发现
(C)上述式(I-b)化合物,其中A、B、Q1、Q2、R1、W、X、Y和Z具有上述含义,可通过如下得到:
上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有上述含义,分别
(α)与式(VI)的酰卤
其中
R1具有上述含义,和
Hal表示卤素(尤其是氯或溴),
或
(β)与式(VII)的酸酐
R1-CO-O-CO-R1 (VII)
其中
R1具有上述含义,
任选在溶剂存在下和任选在酸结合剂存在下反应;(D)上述式(I-c)化合物,其中A、B、Q1、Q2、R2、M、W、X、Y和Z具有上述含义和L表示氧,可如下得到
上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有上述含义,分别与式(VIII)的氯甲酸酯或氯甲酸硫代酯
R2-M-CO-Cl (VIII)
其中
R2和M具有上述含义,
任选在溶剂存在下和任选在酸结合剂存在下反应;(E)上述式(I-c)化合物,其中A、B、Q1、Q2、R2、M、W、X、Y和Z具有上述含义和L表示硫,可如下得到
上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有上述含义,分别与式(IX)的氯一硫代甲酸酯或氯二硫代甲酸酯
其中
M和R2具有上述含义,
任选在溶剂存在下和任选在酸结合剂存在下反应
和
(F)上述式(I-d)化合物,其中A、B、Q1、Q2、R3、W、X、Y和Z具有上述含义,可如下得到:上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有上述含义,分别与式(X)的磺酰氯
R3-SO2-Cl (X)
其中
R3具有上述含义,
任选在溶剂存在下和任选在酸结合剂存在下反应,
(G)上述式(I-e)化合物,其中A、B、L、Q1、Q2、R4、R5、W、X、Y和Z具有上述含义,可如下得到:
上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有上述含义,分别与式(XI)的磷化合物
其中
L、R4和R5具有上述含义,和
Hal表示卤素(尤其是氯或溴),
任选在溶剂存在下和任选在酸结合剂存在下反应,
(H)上述式(I-f)化合物,其中A、B、E、Q1、Q2、W、X、Y和Z具有上述含义,可如下得到:
上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有上述含义,分别与(XII)或(XIII)的金属化合物或胺
Me(OR11)t (XII)
其中
Me表示一或二价金属(优选碱金属或碱土金属,如锂、钠、钾、镁或钙),t表示数字1或2,和
R11、R12、R13各自独立表示氢或烷基(优选C1-C8-烷基),
任选在溶剂存在下反应,
(I)上述式(I-g)化合物,其中A、B、L、Q1、Q2、R6、R7、W、X、Y和Z具有上述含义,可如下得到,
上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有上述含义,分别
(α)与式(XIV)的异氰酸酯或与异硫氰酸酯
R6-N=C=L (XIV)
其中
R6和L具有上述含义,
任选在溶剂存在下和任选在催化剂存在下反应,或
(β)与式(XV)的氨基甲酰氯(Carbamidsurechloriden)或硫代氨基甲酰氯
其中
L、R6和R7具有上述含义,
任选在溶剂存在下和任选在酸结合剂存在下反应。
此外已发现,式(I)的5,6-二氢吡喃酮-衍生物可通过如下制备
(J)下式的硅醇醚
其中
A和B具有上述含义,和
Alk表示具有1-4个碳原子的烷基,
与下式的烯酮-衍生物
其中
W、X、Y和Z具有上述含义,和
Hal表示氯或溴,
任选在溶剂或稀释剂混合物存在下并任选在酸结合剂存在下反应。
此外已发现,新的式(I)化合物作为农药,优选作为杀虫剂、杀螨剂以及作为除草剂具有很好的活性。
本发明化合物通过式(I)进行一般性定义。在上下文中提到的结构式中提及的基团的优选的取代基和范围在下面说明:
W优选表示氢、C1-C6-烷基、C2-C4-链烯基、乙炔基、氟、氯、溴、C1-C4-卤代烷基或C1-C6-烷氧基,
X优选表示氟、氯、溴、C1-C6-烷基、C1-C4-卤代烷基、C1-C6-烷氧基、C2-C4-链烯基、乙炔基、C1-C4-卤代烷氧基、氰基或各自任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基取代的苯基或苄基氧基,
Y优选表示氢、C1-C6-烷基、C1-C4-卤代烷基、氟、氯、溴、C1-C6-烷氧基、C2-C4-链烯基、乙炔基或表示下述基团之一
V1优选表示氢、卤素、C1-C12-烷基、C1-C6-烷氧基、C1-C6-烷基硫基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基、氰基或各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基一或多取代的苯基、苯氧基、苯氧基-C1-C4-烷基、苯基-C1-C4-烷氧基、苯硫基-C1-C4-烷基或苯基-C1-C4-烷基硫基,
V2优选表示氢、氟、氯、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基或C1-C4-卤代烷氧基,
V3优选表示氢、氟、氯、甲基或甲氧基,
Z优选表示氢、氟、氯、溴、C1-C6-烷基、C1-C4-卤代烷基、C1-C6-烷氧基、C1-C4-卤代烷氧基或氰基,
条件是如果Y表示被V1、V2和V3取代的苯基或杂芳基,则W、X和Z不表示溴、C2-C4-链烯基和乙炔基,和第二点,基团W、X和Y最多只有两个可表示C2-C4-链烯基或乙炔基,条件是基团W、X、Y和Z中的其它任何基团都不表示溴,
A优选表示一条键、氢或各自任选被卤素取代的C1-C12-烷基、C3-C8-链烯基、C1-C6-烷氧基-C1-C4-烷基、各自任选被卤素、C1-C4-烷基或C1-C4-烷氧基取代的C3-C8-环烷基或C3-C6-环烷基-C1-C4-烷基,其中任选一或两个不直接相邻的环单元被氧和/或硫代替或表示各自任选被卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、氰基或硝基取代的苯基、苄基、具有5-6个环原子的杂芳基(例如呋喃基、吡啶基、咪唑基、三唑基、吡唑基、嘧啶基、噻唑基或噻吩基)或具有5-6个环原子的杂芳基-C1-C4-烷基(例如吡啶基、嘧啶基或噻唑基),
B优选表示氢或C1-C6-烷基,或
A、B和与其相连的碳原子优选表示饱和的C3-C10-环烷基或不饱和的C5-C10-环烷基,其中任选一个环单元被氧或硫代替并且其任选被C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-烷基硫基、卤素或苯基一或二取代,条件是,Q1和Q2不形成另外的环,或
B和Q1一起优选表示各自任选被相同或不同的C1-C4-烷基一或二取代的C3-C6-链烷二基,其中两个不相邻的碳原子任选形成另一3-至6-元环,或
Q1优选表示氢、羟基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-烷氧基-C1-C2-烷基、C1-C6-烷基酰基氧基,任选被氟、氯、C1-C4-烷基、C1-C2-卤代烷基或C1-C4-烷氧基取代的C3-C8-环烷基,其中任选一个亚甲基被氧或硫代替或任选被卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基取代的苯基,
Q2优选表示氢或C1-C4-烷基,或
Q1和Q2和与其连接的碳原子一起优选表示任选被C1-C6-烷基、C1-C6-烷氧基或C1-C2-卤代烷基取代的C3-C7-环烷基,其中任选一个环单元被氧或硫代替,条件是A和B不形成另一个环,
G优选表示氢(a)或下列基团之一
尤其是表示(a)、(b)或(c),
其中
E表示金属离子或铵离子,
L表示氧或硫,和
M表示氧或硫。
R1优选表示各自任选被卤素取代的C1-C20-烷基、C2-C20-链烯基、C1-C8-烷氧基-C1-C8-烷基、C1-C8-烷基硫基-C1-C8-烷基、多-C1-C8-烷氧基-C1-C8-烷基或任选被卤素、C1-C6-烷基或C1-C6-烷氧基取代的C3-C8-环烷基,其中任选一个或多个(优选一个或两个)不直接相邻的环单元被氧和/或硫代替,或
表示任选被卤素、氰基、硝基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C1-C6-烷基硫基或C1-C6-烷基磺酰基取代的苯基,或
表示任选被卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基或C1-C6-卤代烷氧基取代的苯基-C1-C6-烷基,或表示任选被卤素、C1-C6-烷基或三氟甲基取代的5-或6-元杂芳基(例如吡唑基、噻唑基、吡啶基、嘧啶基、呋喃基或噻吩基),或表示任选被卤素或C1-C6-烷基取代的苯氧基-C1-C6-烷基,或表示任选被卤素、氨基或C1-C6-烷基取代的5-或6-元杂芳基氧基-C1-C6-烷基(例如吡啶基氧基-C1-C6-烷基、嘧啶基氧基-C1-C6-烷基或噻唑基氧基-C1-C6-烷基),
R2优选表示各自任选被卤素取代的C1-C20-烷基、C2-C20-链烯基、C1-C8-烷氧基-C2-C8-烷基、多-C1-C8-烷氧基-C2-C8-烷基,或
表示任选被卤素、C1-C6-烷基或C1-C6-烷氧基取代的C3-C8-环烷基,
或
表示各自任选被卤素、氰基、硝基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基或C1-C6-卤代烷氧基取代的苯基或苄基,
R3优选表示任选被卤素取代的C1-C8-烷基或表示各自任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基取代的苯基或苄基,
R4和R5优选各自独立表示各自任选被卤素取代的C1-C8-烷基、C1-C8-烷氧基、C1-C8-烷基氨基、二-(C1-C8-烷基)氨基、C1-C9-烷基硫基、C2-C8-链烯基硫基、C3-C7-环烷基硫基或表示各自任选被卤素、硝基、氰基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷基硫基、C1-C4-卤代烷基硫基、C1-C4-烷基或C1-C4-卤代烷基取代的苯基、苄基、苯氧基或苯硫基,
R6和R7各自独立优选表示氢、表示各自任选被卤素取代的C1-C8-烷基、C3-C8-环烷基、C1-C8-烷氧基、C3-C8-链烯基、C1-C8-烷氧基-C1-C8-烷基,表示任选被卤素、C1-C8-卤代烷基、C1-C8-烷基或C1-C8-烷氧基取代的苯基,任选被卤素、C1-C8-烷基、C1-C8-卤代烷基或C1-C8-烷氧基取代的苄基或一起表示任选被C1-C4-烷基取代的C3-C6-亚烷基,其中任选一个碳原子被氧或硫代替。
在作为优选提到的基团定义中,卤素,也包括作为取代基,例如在卤代烷基中,表示氟、氯、溴和碘,尤其是表示氟和氯。
W特别优选表示氢、C1-C4-烷基、氯或溴,
X特别优选表示氯、溴、C1-C4-烷基、C1-C4-烷氧基、C2-C3-链烯基、乙炔基、C1-C2-卤代烷基、C1-C2-卤代烷氧基或氰基。
Y特别优选表示氢、C1-C4-烷基、C1-C2-卤代烷基、氟、氯、溴、C1-C4-烷氧基、C2-C3-链烯基、乙炔基、2-噻吩基、3-噻吩基或基团
V1特别优选表示氢、氟、氯、溴、C1-C6-烷基、C1-C4-烷氧基、C1-C4-烷基硫基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基、氰基或苯基,
V2特别优选表示氢、氟、氯、C1-C4-烷基、C1-C4-烷氧基或C1-C2-卤代烷基,
Z特别优选表示氢、氟、氯、溴、C1-C4-烷基、C1-C2-卤代烷基、C1-C4--烷氧基或C1-C2-卤代烷氧基,
第一个条件是,如果Y表示被V1和V2取代的苯基、2-噻吩基或3-噻吩基,则W、X和Z不表示溴、C2-C3-链烯基和乙炔基,并且第二个条件是基团W、X和Y只有一个可表示C2-C3-链烯基和乙炔基,条件是W、X、Y和Z中其它基团都不能表示溴。
A特别优选表示一条键、氢、各自任选被氟取代的C1-C8-烷基、C1-C4-烷氧基-C1-C2-烷基,各自任选被氟、氯、甲基、乙基或甲氧基取代的C5-C6-环烷基或C3-C6-环烷基-C1-C2-烷基,其中任选一个环单元被氧或硫代替或各自任选被氟、氯、溴、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基或C1-C2-卤代烷氧基取代的苯基或苄基。
B特别优选表示氢或C1-C4-烷基,或
A、B和与其相连的碳原子特别优选表示饱和的C5-C7-环烷基,其中任选一个环单元被氧代替并且其任选被C1-C4-烷基、三氟甲基或C1-C4-烷氧基一取代,条件是Q1和Q2不形成另外的环,或
B和Q1一起特别优选表示任选被C1-C2-烷基一取代的C3-C4-链烷二基,
其中两个不直接相邻的碳原子任选形成另一个五至六元环,或
Q1特别优选表示氢、羟基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C2-烷基、C1-C4--烷基酰基氧基或任选被甲基或甲氧基取代的C3-C6-环烷基,其中任选一个亚甲基被氧代替,
Q2特别优选表示氢、甲基或乙基,或
Q1和Q2和与其相连的碳原子一起特别优选表示任选被C1-C4-烷基、三氟甲基或C1-C4-烷氧基取代的饱和C5-C6-环烷基,其中任选一个环单元被氧代替,条件是A和B不形成另外的环,
G特别优选表示氢(a)或下列基团之一
尤其是表示(a)、(b)或(c),
其中
E表示金属离子或铵离子,
L表示氧或硫,或
M表示氧或硫,
R1特别优选表示各自任选被氟或氯取代的C1-C16-烷基、C2-C16-链烯基、C1-C4-烷氧基-C1-C2-烷基、C1-C4-烷基硫基-C1-C2-烷基,或任选被氟、氯、C1-C2-烷基或C1-C2-烷氧基取代的C3-C7-环烷基,其中任选一或两个不直接相邻的环单元被氧和/或硫代替,或表示任选被氟、氯、溴、氰基、硝基、C1-C4-烷基、C1-C4-烷氧基、三氟甲基或三氟甲氧基一或二取代的苯基,或表示各自任选被氟、氯、溴、甲基、乙基或三氟甲基一取代的吡啶基或噻吩基,
R2特别优选表示各自任选被氟一到三取代的C1-C16-烷基、C2-C16-链烯基或C1-C4-烷氧基-C2-C4-烷基,
表示任选被甲基、乙基或甲氧基一取代的C3-C7-环烷基,或
表示各自任选被氟、氯、溴、氰基、硝基、C1-C4-烷基、C1-C3-烷氧基、三氟甲基或三氟甲氧基一或二取代的苯基或苄基,
R3特别优选表示任选被氟一到五取代的C1-C6-烷基或表示各自任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、三氟甲氧基、氰基或硝基一或二取代的苯基,
R4特别优选表示C1-C6-烷基、C1-C6-烷氧基、C1-C6-烷基氨基、二-(C1-C6-烷基)氨基、C1-C6-烷基硫基,或表示各自任选被氟、氯、溴、硝基、氰基、C1-C3-烷氧基、三氟甲氧基、C1-C3-烷基或三氟甲基一或二取代的苯基、苄基、苯氧基或苯硫基,
R5特别优选表示C1-C4-烷基、C1-C4-烷氧基或C1-C4-烷基硫基,
R6特别优选表示C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基、C3-C6-链烯基、C1-C6-烷氧基-C1-C6-烷基,或表示任选被氟、氯、溴、三氟甲基、C1-C4-烷基或C1-C4-烷氧基一或二取代的苯基,或表示任选被氟、氯、溴、甲基、乙基、三氟甲基或甲氧基一或二取代的苄基,
R7特别优选表示氢、C1-C6-烷基或C3-C6-链烯基,或
R6和R7一起特别优选表示任选被甲基或乙基一或二取代的C4-C5-亚烷基,其中任选一个亚甲基被氧或硫代替。
在所提及的特别优选的取代基定义中,卤素,也作为取代基的卤素,例如在卤代烷基中的卤素,代表氟、氯、溴和碘,特别是氟和氯,特别优选是氟。
W非常特别优选代表氢、氯、溴、甲基或乙基,
X非常特别优选代表氯、溴、甲基、乙基、正丙基、甲氧基、乙氧基、三氟甲基、二氟甲氧基、三氟甲氧基或氰基(尤其是氯、溴、甲基、乙基、正丙基或三氟甲基),
Y非常特别优选代表氢、甲基、乙基、丙基、异丙基、三氟甲基、氟、氯、溴、甲氧基、或代表如下所示的基团
V1非常特别优选代表氢、氟、氯、溴、甲基、乙基、异丙基、叔丁基、甲氧基、三氟甲基或三氟甲氧基、氰基或苯基,
V2非常特别优选代表氢、氟、氯、甲基或三氟甲基,
Z非常特别优选代表氢、氟、氯、溴、甲基、甲氧基或三氟甲基(尤其是氢、氟、氯、溴或甲基),条件是:如果Y代表被V1和V2取代的苯基,则W、X和Z不代表溴。
A非常特别优选代表一条键、氢、甲基、乙基、正丙基、异丙基、正丁基或异丁基。
B非常特别优选代表氢、甲基或乙基,或
A、B与它们所连接的碳原子一起非常特别优选代表饱和的C5-C6-环烷基,其中任选有一个环单元被氧替代,并且所述环烷基任选被下列基团单取代:甲基、乙基、甲氧基或乙氧基,条件是Q1和Q2不形成其它环,或
B与Q1一起非常特别优选代表任选被甲基单取代的C3-C4-烷二基,其中两个不直接相邻的碳原子任选形成另一三至六元环,或
Q1非常特别优选代表氢、羟基、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、丙氧基、乙酰基氧基或丙酰基氧基,
Q2非常特别优选代表氢、甲基或乙基,或
Q1和Q2与它们所连接的碳原子一起非常特别优选代表任选被甲基、乙基、甲氧基、乙氧基、丙氧基或丁氧基取代的饱和C6-环烷基,其中任选有一个环单元被氧替代,条件是A和B不形成另外的环,
G非常特别优选代表氢(a)或代表下列基团之一
尤其是代表(a)、(b)或(c),
其中
E代表金属离子或铵离子,
L代表氧(在(c)的情况下特别优选)或硫,且
M代表氧或硫.
R1非常特别优选代表分别任选被氟或氯取代的C1-C8-烷基、C2-C8-链烯基、C1-C2-烷氧基-C1-烷基、C1-C2-烷硫基-C1-烷基、环丙基、环戊基或环己基,或
代表任选被下列基团一取代的苯基:氟、氯、溴、氰基、硝基、甲基、乙基、异丙基、叔丁基、甲氧基、三氟甲基或三氟甲氧基,或代表分别任选被氟、氯、溴或甲基一取代的噻吩基或吡啶基,
R2非常特别优选代表C1-C8-烷基、C2-C8-链烯基或C1-C4-烷氧基-C2-烷基、或环己基,
或代表分别任选被下列基团一取代的苯基或苄基:氟、氯、溴、氰基、硝基、甲基、叔丁基、甲氧基、三氟甲基或三氟甲氧基,
R3非常特别优选代表甲基、乙基、正丙基、或任选被氟、氯、溴、甲基、叔丁基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一取代的苯基,
R4非常特别优选代表C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷基氨基、二-(C1-C4-烷基)氨基、C1-C4-烷硫基,或代表分别任选被氟、氯、溴、硝基、氰基、C1-C2-烷氧基、三氟甲氧基或C1-C3-烷基一取代的苯基、苯氧基或苯硫基,
R5非常特别优选代表甲基、乙基、甲氧基、乙氧基、甲硫基或乙硫基,
R6非常特别优选代表C1-C4-烷基、C3-C6-环烷基、C1-C4-烷氧基、C3-C4-链烯基、C1-C4-烷氧基-C1-C4-烷基,
R7非常特别优选代表氢,代表C1-C4-烷基或C3-C4-链烯基,
R6和R7一起非常特别优选代表C6-亚烷基,其中任选有一个亚甲基被氧或硫替代。
W最优选代表氢、甲基、乙基、氯或溴,
X最优选代表甲基、乙基、正丙基、三氟甲基或氯,
Y最优选代表甲基、三氟甲基、氯、溴,代表任选被氯和/或甲基一或二取代的苯基,
Z最优选代表氢或甲基,条件是如果Y代表苯基,则W不代表溴,
A最优选代表甲基、乙基或一条键,
B最优选代表甲基或乙基,或
A、B与它们所连接的碳原子一起最优选代表环丙基或环己基,或,
B和Q1一起最优选代表任选被甲基一取代的C4-烷二基,
Q1最优选代表氢、甲基、甲氧基、乙氧基、丙氧基、羟基或乙酰基氧基,
Q2最优选代表氢或甲基,
G最优选代表氢(a)或代表下列基团之一
其中
R1最优选代表C1-C4-烷基或代表各自任选被氯一取代的苯基或吡啶基,
R2最优选代表C1-C4-烷基。
上述一般或优选的基团定义或说明可彼此根据需要组合,即包括各个范围和优选范围之间的组合。这既适用于终产物,也相应地适用于前体和中间体。
依据本发明,包含上述优选含义的组合的式(I)化合物是优选的。
依据本发明,包含上述特别优选含义的组合的式(I)化合物是特别优选的。
依据本发明,包含上述非常特别优选含义的组合的式(I)化合物是非常特别优选的。
依据本发明,包含上述最优选含义的组合的式(I)化合物是最优选的。
饱和或不饱和烃基例如烷基或链烯基,包括与杂原子连接的,例如烷氧基,只要可能,各自可以是直链或支链的。
除非另有说明,否则任选取代的基团可以是单取代或多取代,对于多取代,取代基可相同或不同。
依据方法(A),如果使用O-[(2,4-二氯)-苯基乙酰基]-1-羟基甲基-环己烷-甲酸乙酯作为原料,该本发明方法可由下述反应路线表示:
依据方法(Bγ),如果使用3-[(2-氯-4-溴-6-甲基)-苯基]-5,5,6,6-四甲基-5,6-二氢吡喃酮和4-氯苯基硼酸作为原料,该反应可由下述反应路线表示:
依据方法(Cα),如果使用3-[(2,4-二氯)-苯基]-5,5,6,6-四甲基-5,6-二氢吡喃酮和新戊酰氯作为原料,该本发明方法可由下述反应路线表示:
依据方法(Cβ),如果使用3-[(4-溴-2-氯-6-乙基)-苯基]-6,6-二甲基-5,6-二氢吡喃酮和乙酸酐作为原料,该本发明方法可由下述反应路线表示:
依据方法(D),如果使用3-[(2-氯-6-乙基-4-苯基)-苯基]-5,5-二甲基-5,6-二氢吡喃酮和氯甲酸乙氧基乙酯作为原料,该本发明方法可由下述反应路线表示:
依据方法(E),如果使用3-[2,4,6-三氯-苯基]-5,5,6,6-四甲基-5,6-二氢吡喃酮和氯一硫代甲酸甲酯作为原料,该反应可由下述反应路线表示:
依据方法(F),如果使用3-(4-氯-2-甲基苯基)-5,5-二甲基-6-甲氧基-5,6-二氢吡喃酮和甲磺酰氯作为原料,该反应可由下述反应路线表示:
依据方法(G),如果使用2-(2-甲基-5-溴-苯基)-5,5,6,6-四甲基-5,6-二氢吡喃酮和甲烷硫代磷酰氯(2,2,2-三氟乙基酯)作为原料,该反应可由下述反应路线表示:
依据方法(H),如果使用3-(2,4-二氯-苯基)-5,5-五亚甲基-6-甲氧基-5,6-二氢吡喃酮和NaOH作为反应组分,该本发明方法可由下述反应路线表示:
依据方法(Iα),如果使用3-(2,4-二氯-苯基)-5,5,6,6-四甲基-5,6-二氢吡喃酮和异氰酸乙酯作为原料,该反应可由下述反应路线表示:
依据方法(Iβ),如果使用3-(2-氯-4-溴-苯基)-5,5-二甲基-6-甲氧基-5,6-二氢吡喃酮和二甲基氨基甲酰氯作为原料,该反应可由下述反应路线表示:
如果用(氯羰基)-2-(1,3,5-三甲基苯基)烯酮和三甲基甲硅烷氧基亚甲基环己烷作为原料,则本发明方法(J)可由下述反应路线表示:
在本发明方法(A)中需要作为原料的式(II)化合物是新的
其中
A、B、Q1、Q2、W、X、Y、Z和R8具有上述含义。
式(II)的酰基羟基羧酸酯,例如通过如下得到:
式(XVIII)的羟基羧酸酯
其中
A、B、Q1、Q2和R8各具有上述含义,
与式(XIX)取代的苯乙酰卤
其中
W、X、Y和Z各具有上述含义,和
Hal表示氯或溴,
发生酰化反应(参见式(II)化合物的制备实施例)。
部分式(XVIII)化合物是已知的或可根据原则上已知的方法,例如通过Reformatskij合成制备(Organikum,VEB Deutscher Verlagder Wissenschaften,Berlin 1990,第18版,501页起)。
部分式(XIX)化合物是已知的并可商购。它们可以通过原则上已知的方法合成(参见例如H.Henecka,Houben-Weyl,Methoden derOrganischen Chemie,第8版,467-469页(1952),WO 97/02243,WO 99/43649)。
式(XIX)化合物例如通过式(XX)取代的苯乙酸
其中
W、X、Y和Z各具有上述含义,
与卤化剂(例如亚硫酰氯、亚硫酰溴、草酰氯、光气、三氯化磷、三溴化磷或五氯化磷)任选在溶剂存在下(例如任选氯代脂肪或芳香烃,如甲苯或二氯甲烷)、在-20℃-150℃,优选-10℃-100℃温度下反应。
部分式(XX)化合物是可商购的、部分是已知的或可按照原则上已知的方法制备(例如WO 97/02243、WO 99/43649)。
部分实施方法B(α)所需的式(III)的甲硅烷基乙炔是可商购的或可按照常规已知的方法制备。部分实施方法B(β)所需的式(IV)的乙烯基锡烷同样是可商购的或可按照已知的方法制备。
部分实施方法B(γ)所需的式(V)的硼酸
其中
Y表示任选取代的苯基或杂芳基,
是可商购的或可按照常规已知的方法简单地制备。
实施本发明方法(J)中所需作为原料的甲硅烷醇醚是通过式(XVI)进行一般定义的。在该结构式中,A和B各优选具有在关于本发明式(I)的5,6-二氢-吡喃酮的描述中已提及的关于所述基团优选的含义。Alk优选表示甲基或乙基,特别优选表示甲基。
式(XVI)的甲硅烷醇醚是已知的或可按照已知方法制备。
实施本发明方法所需的作为反应组分的烯酮-衍生物是通过式(XIV)进行一般定义的,在该结构式中,W、X、Y和Z各优选具有在关于本发明式(I)的5,6-二氢-吡喃酮的描述中已提及的关于所述基团优选的含义。Hal也优选表示氯或溴。
式(XVII)的烯酮衍生物是已知的或可按照已知的方法制备(参见Org.Prep.Proced.Int.7,155-158(1975)和DE-A 19 45 703)。因此,式(XVII)的烯酮衍生物可通过式(XXI)取代的苯基丙二酸
其中
W、X、Y和Z各具有上述含义,
与酰卤,例如亚硫酰氯、五氯化磷、三氯化磷、草酰氯、光气或亚硫酰溴,任选在催化剂,例如二乙基甲酰胺、甲基-Steryl甲酰胺或三苯膦存在下,并任选在碱例如吡啶或三乙胺存在下,在-20℃至+200℃,优选0℃-150℃温度下反应得到。
式(XXI)取代的苯基丙二酸是已知的或可按已知方法制备(参见例如Organikum,VEB Deutscher Verlag der Wissenschaften,Berlin1977,517页起)。因此,式(XXI)取代的苯基丙二酸通过下式的取代的苯基丙二酸酯
其中
W、X、Y和Z各具有上述含义,和
R9表示具有1-4个碳原子的烷基,
与碱金属氢氧化物,如氢氧化钠或氢氧化钾,在溶剂例如水存在下,在0℃-30℃的温度下反应得到。
在式(XXII)中,优选W、X、Y和Z具有在关于本发明式(I)的5,6-二氢-吡喃酮的描述中已提及的关于所述基团优选的含义。R9优选表示甲基或乙基。
式(XXII)取代的苯基丙二酸酯是已知的或可按已知方法制备(参见Tetrahedron Letters 27,2763(1986)和Organikum,VEBDeutscher Verlag der Wissenschaften,Berlin 1977,587页起)。
此外,用于实施本发明方法(C)、(D)、(E)、(F)、(G)、(H)和(I)所需的作为原料的式(VI)的酰卤、式(VII)的酸酐、式(VIII)的氯甲酸酯或氯甲酸硫代酯、式(IX)的氯一硫代甲酸酯或氯二硫代甲酸酯、式(X)的磺酰氯、式(XI)的磷化合物和式(XII)和(XIII)的金属氢氧化物、金属醇化物或胺和式(XIV)的异氰酸酯及式(XV)的氨基甲酰氯是一般已知的有机或无机化学的化合物。
方法(A)的特征是式(II)化合物,其中A、B、Q1、Q2、W、X、Y、Z和R8各具有上述含义,在碱存在下进行分子内缩合反应。
在本发明方法(A)中所用的合适的溶剂可以是所有惰性有机溶剂。可优选应用的是烃类,如甲苯和二甲苯,以及醚类,如二丁基醚、四氢呋喃、二噁烷、乙二醇二甲基醚和二乙二醇二甲基醚,此外是极性溶剂,如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基吡咯烷酮,以及醇类,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
适用于实施本发明方法(A)的碱(去质子化剂)是所有常用的质子受体。优选使用碱金属和碱土金属氧化物、氢氧化物和碳酸盐,例如氢氧化钠、氢氧化钾、氧化镁、氧化钙、碳酸钠、碳酸钾和碳酸钙,这些碱还可以在相转移催化剂例如三乙基苄基氯化铵、四丁基溴化铵、Adogen 464(=甲基三烷基(C8-C10)氯化铵)或TDA 1(=三-(甲氧基乙氧基乙基)胺)存在下使用。也可以使用碱金属例如钠或钾。此外可应用碱金属和碱土金属氨化物和氢化物例如氨化钠、氢化钠和氢化钙,以及碱金属醇化物例如甲醇钠、乙醇钠和叔丁醇钾。
当实施本发明方法(A)时,反应温度可以在较宽的范围内变化。反应一般在0℃-250℃、优选50℃-150℃温度下进行。
本发明方法(A)一般在常压下进行。
当实施本发明方法(A)时,式(II)反应组分和去质子化碱一般以大约两倍摩尔量使用。然而,可使用较大过量(最高达3摩尔)的一种组分或另一种组分。
适用于实施本发明方法B(α)-B(γ)的催化剂是钯(0)络合物。使用例如四-(三苯基膦)钯。钯(II)化合物例如二(三苯基膦)氯化钯(II)也是合适的。
适用于实施本发明方法B(α)和B(γ)的酸接受体是无机碱或有机碱。这些碱优选包括碱土金属或碱金属氢氧化物、乙酸盐、碳酸盐或碳酸氢盐,例如氢氧化钠、氢氧化钾、氢氧化钡或氢氧化铵、乙酸钠、乙酸钾、乙酸钙或乙酸铵、碳酸钠、碳酸钾或碳酸铵、碳酸氢钠或碳酸氢钾,碱金属氟化物例如氟化钾或氟化铯,以及叔胺例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄基胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)、或二氮杂二环十一碳烯(DBU)。
适用于实施本发明方法B(γ)的稀释剂是水、有机溶剂及其任意混合物。对于方法B(α)-B(γ),可以以举例方式提及的有机溶剂有:脂族、脂环族或芳族烃类,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢萘;卤代烃类例如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷、三氯乙烷或四氯乙烯;醚类例如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二氧杂环己烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二甘醇二甲醚或茴香醚;醇类例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、乙二醇、丙-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二甘醇一甲醚;二甘醇一乙醚;水。
当实施本发明方法(B)时,反应温度可以在较宽的范围内变化。反应一般在0℃-+180℃、优选+50℃-+150℃温度下进行。
当实施方法B(α)时,式(III)甲硅烷基乙炔与式(I-a′)-(I-g′)化合物以1∶1-10∶1、优选1∶1-3∶1的摩尔比使用。当实施方法B(β)时,式(IV)乙烯基甲锡烷与式(I-a′)-(I-g′)化合物以1∶1-10∶1、优选1∶1-3∶1的摩尔比使用。
当实施本发明方法B(γ)时,式(V)硼酸与式(I-a′)-(I-g′)化合物以1∶1-3∶1、优选1∶1-2∶1的摩尔比使用。
按化合物(I-1-a′)-(I-1-g′)的量为1摩尔计,催化剂一般以0.005-0.5摩尔、优选0.01摩尔-0.1摩尔的量使用。碱通常过量使用。
方法(C-α)的特征在于,将式(I-a)化合物分别与式(VI)酰卤反应,该反应任选在稀释剂存在下,以及任选在酸结合剂存在下进行。
适用于本发明方法(C-α)的稀释剂是对酰卤呈惰性的所有溶剂。优选使用烃类例如汽油、苯、甲苯、二甲苯和十氢萘,卤代烃类例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,酮类例如丙酮和甲基异丙基酮,醚类例如乙醚、四氢呋喃和二氧杂环己烷,羧酸酯类例如乙酸乙酯,腈类例如乙腈,以及强极性溶剂例如二甲基甲酰胺、二甲亚砜和环丁砜。如果酰卤水解稳定,那么该反应也可以在水存在下进行。
适用于本发明方法(C-α)的酸结合剂是所有常用的酸结合剂。优选使用叔胺例如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环十一碳烯(DBU)、二氮杂二环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,碱土金属氧化物例如氧化镁和氧化钙,碱金属和碱土金属碳酸盐例如碳酸钠、碳酸钾和碳酸钙,以及碱金属氢氧化物例如氢氧化钠和氢氧化钾。
本发明方法(C-α)的反应温度可以在较宽的范围内变化。反应一般在-20℃-+150℃、优选0℃-100℃温度下进行。
当实施本发明方法(C-α)时,式(I-a)原料与式(VI)酰卤一般以大约等摩尔量使用。然而,也可以使用较大过量(最高达5摩尔)的酰卤。通过常规方法进行后处理。
方法(C-β)的特征在于,将式(I-a)化合物与式(VII)羧酸酐反应,该反应在稀释剂存在下,以及任选在酸结合剂存在下进行。
对于本发明方法(C-β),优选应用的稀释剂是在使用酰卤时也优选的那些稀释剂。此外,过量使用的羧酸酐也可以同时起稀释剂的作用。
在方法(C-β)中,任选加入的酸结合剂优选为在使用酰卤时也优选的那些酸结合剂。
在本发明方法(C-β)中,反应温度可以在较宽的范围内变化。反应一般在-20℃-+150℃、优选0℃-100℃温度下进行。
当实施本发明方法(C-β)时,式(I-a)原料与式(VII)羧酸酐一般以大约等摩尔量使用。然而,也可以使用较大过量(最高达5摩尔)的羧酸酐。通过常规方法进行后处理。
一般情况下,对于所采用的方法,通过蒸馏或者通过用有机溶剂或水洗涤来除去稀释剂和过量羧酸酐以及所形成的羧酸。
方法(D)的特征在于,将式(I-a)化合物分别与式(VIII)氯甲酸酯或氯甲酸硫代酯反应,该反应任选在稀释剂存在下,并任选在酸结合剂存在下进行。
适用于本发明方法(D)的酸结合剂是所有常用的酸结合剂。可优选使用叔胺例如三乙胺、吡啶、DABCO、DBU、DBN、Hünig碱和N,N-二甲基苯胺,碱土金属氧化物例如氧化镁和氧化钙,碱金属碳酸盐和碱土金属碳酸盐例如碳酸钠、碳酸钾和碳酸钙,以及碱金属氢氧化物例如氢氧化钠和氢氧化钾。
适用于本发明方法(D)的稀释剂是对氯甲酸酯或氯甲酸硫代酯呈惰性的所有溶剂。优选使用烃类例如汽油、苯、甲苯、二甲苯和十氢萘,卤代烃类例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,酮类例如丙酮和甲基异丙基酮,醚类例如乙醚、四氢呋喃和二氧杂环己烷,羧酸酯类例如乙酸乙酯,腈类例如乙腈,以及强极性溶剂例如二甲基甲酰胺、二甲亚砜和环丁砜。
当实施本发明方法(D)时,反应温度可在较宽的温度范围内改变。如果反应是在稀释剂和酸结合剂存在下进行,反应温度一般为-20℃-+100℃,优选0℃-50℃。
本发明方法(D)一般在常压下进行。
当进行本发明方法(D)时,式(I-a)原料与相应的式(VIII)氯甲酸酯或氯甲酸硫代酯一般以大约等摩尔量使用。然而,还可以使用较大过量(最高达2摩尔)的一种组分或另一种组分。通过常规方法进行后处理。一般除去沉淀的盐,并通过将稀释剂汽提来将剩余的反应混合物浓缩。
本发明方法(E)的特征在于,将式(I-a)化合物分别与式(IX)化合物在稀释剂存在下、并任选在酸结合剂存在下反应。
在制备方法(E)中,按式(I-a)原料的量为1摩尔计,使用大约1摩尔式(IX)氯一硫代甲酸酯或氯二硫代甲酸酯于0-120℃、优选20-60℃进行反应。
任选加入的稀释剂合适的是所有惰性极性有机溶剂,例如腈、醚、酯、酰胺、砜、亚砜、以及卤代烷烃。
优选使用乙腈、乙酸乙酯、二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果在优选的实施方案中,化合物(I-a)的烯醇型盐是通过加入强去质子化剂例如氢化钠或叔丁醇钾而制得的,则无需加入另外的酸结合剂。
如果使用酸结合剂,它们是常规无机碱或有机碱,例如可提及氢氧化钠、碳酸钠、碳酸钾、吡啶、三乙胺。
该反应可在常压下或高压下进行,优选在常压下进行。通过常规方法进行后处理。
本发明方法(F)的特征在于,将式(I-a)化合物与式(X)磺酰氯反应,该反应任选在稀释剂存在下,以及任选在酸结合剂存在下进行。
在制备方法(F)中,按式(I-a)原料的量为1摩尔计,用大约1摩尔式(X)磺酰氯于-20-150℃、优选20-70℃进行反应。
任选加入的稀释剂合适的是所有惰性极性有机溶剂,例如酯、醚、酰胺、腈、砜、亚砜、或卤代烃例如二氯甲烷。
优选使用乙腈、乙酸乙酯、二甲亚砜、四氢呋喃、二甲基甲酰胺、二氯甲烷。
如果在优选的实施方案中,化合物(I-a)的烯醇型盐是通过加入强去质子化剂(例如氢化钠或叔丁醇钾)而制得的,则无需加入另外的酸结合剂。
如果使用酸结合剂,它们是常规无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、吡啶、三乙胺。
该反应可在常压下或高压下进行,优选在常压下进行。通过常规方法进行后处理。
本发明方法(G)的特征在于,将式(I-a)化合物分别与式(XI)磷化合物反应,该反应任选在稀释剂存在下,以及任选在酸结合剂存在下进行。
在方法(G)中,按化合物(I-a)的量为1摩尔计,用1-2、优选1-1.3摩尔式(XI)磷化合物于-40℃-150℃、优选-10-110℃温度下进行反应,以生成式(I-e)化合物。
任选加入的稀释剂合适的是所有惰性极性有机溶剂,例如醚、酰胺、腈、醇、硫醚、砜、亚砜等。
优选使用乙腈、二甲亚砜、四氢呋喃、二甲基甲酰胺、二氯甲烷。
任选加入的酸结合剂合适的是常规无机碱或有机碱,例如氢氧化物、碳酸盐或胺。实例包括氢氧化钠、碳酸钠、碳酸钾、吡啶、三乙胺。
反应可在常压下或高压下进行,优选在常压下进行。通过常规有机化学方法进行后处理。优选通过结晶、色谱纯化或所谓的“初期蒸馏”—即减压除去挥发性组分—纯化所得终产物。
方法(H)的特征在于,将式(I-a)化合物与式(XII)金属氢氧化物或或醇化物或者式(XIII)胺反应,该反应任选在稀释剂存在下进行。
对于本发明方法(H),优选的稀释剂是醚类例如四氢呋喃、二氧杂环己烷、乙醚,或醇类例如甲醇、乙醇、异丙醇,以及水。
本发明方法(H)一般在常压下进行。
反应温度一般为-20℃-100℃、优选0℃-50℃。
本发明方法(I)的特征在于,(I-α):将式(I-a)化合物与式(XIV)化合物反应,该反应任选在稀释剂存在下,以及任选在催化剂存在下进行,或者(I-β):将式(I-a)化合物与式(XV)化合物反应,该反应任选在稀释剂存在下,以及任选在酸结合剂存在下进行。
在制备方法(I-α)中,按式(I-a)原料的量为1摩尔计,用大约1摩尔式(XIV)异氰酸酯于0-100℃、优选20-50℃进行反应。
任选加入的稀释剂合适的是所有惰性有机溶剂,例如腈、酯、醚、酰胺、砜、亚砜。
可任选加入催化剂来促进反应。非常有利的催化剂是有机锡化合物,例如二丁基锡二月桂酸盐(Dibutylzinndilaurat)。该反应优选在常压下进行。
在制备方法(I-β)中,按式(I-a)原料的量为1摩尔计,用大约1摩尔式(XV)氨基甲酰氯于-20-150℃、优选0-70℃进行反应。
任选加入的稀释剂合适的是所有惰性有机溶剂,例如腈、酯、醚、酰胺、砜、亚砜、或卤代烃。
优选使用乙腈、乙酸乙酯、二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果在优选的实施方案中,化合物(Ia)的烯醇盐是通过加入强去质子化剂(例如氢化钠或叔丁醇钾)而制得的,则无需加入另外的酸结合剂。
如果使用酸结合剂,它们是常规无机碱或有机碱,例如氢氧化钠、碳酸钠、碳酸钾、三乙胺或吡啶。
该反应可在常压下或高压下进行,优选在常压下进行。通过常规方法进行后处理。
在实施本发明方法(J)中所用的稀释剂可以是所有常规的、对该反应的组分惰性的有机溶剂。优选可用的是烃类,如间二氯苯、1,2,3,4-四氢化萘、甲苯和二甲苯,此外是醚类,如二丁基醚、乙二醇二甲基醚和二乙二醇二甲基醚,还有极性溶剂,如二甲亚砜、环丁砜、二甲基甲酰胺或N-甲基吡咯烷酮。作为助溶剂可按照实施例(I-2-a)用醇类,如甲醇、乙醇、丙醇、丁醇,以及水。
在实施本发明方法(J)中所用的酸接受剂可以是所有常规的酸结合剂,优选可用叔胺,如三乙胺、吡啶、二氮杂环辛烷(DABCO)、二氮杂双环十一烯(DBU)、二氮杂双环壬烯(DBN)、Hünig碱或N,N-二甲基苯胺。
在实施本发明方法(J)中的反应温度可在一个较大的范围内变化。适当的温度是在0℃-250℃,优选50℃-220℃。
本发明方法(J)优选在常压下实施。
在实施本发明方法(J)中,一般1摩尔式(XVI)的甲硅烷基醚加入等摩尔量式(XVII)的烯酮-衍生物和任选也加入等摩尔量的酸接受剂。但也可以较大过量地应用一种或另一种组分(至多5摩尔)。
本发明式(I)的5,6-二氢-吡喃酮具有很好的杀虫作用并对农作物具有很好的耐受性。
本发明活性化合物适于控制动物害虫,特别是在农业、林业、储藏产品和材料的保护,以及卫生领域中发生的昆虫、蜘蛛类动物和线虫,同时具有很好的植物耐受性以及对恒温动物的可接受的毒性。它们可优选用作农作物保护剂。它们对正常敏感和抗性种类以及对所有或某些发育阶段都具有活性。上述害虫包括:
等足目:例如潮虫(Oniscus asellus)、平甲虫和鼠妇。
倍足目:例如具斑马陆。
唇足目:例如食果地蜈蚣和蚰蜓属。
综合目:例如庭园么蚰。
缨尾目:例如台湾衣鱼。
弹尾目:例如武装棘跳虫。
直翅目:例如家蟋蟀、蝼蛄属、非洲飞蝗、黑蝗属和沙漠蝗。
蜚蠊目:例如东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国小蠊。
革翅目:例如欧洲球螋。
等翅目:例如散白蚁属。
虱目:例如体虱、血虱属、颚虱属、嚼虱属和畜虱属。
缨翅目:例如温室条蓟马、烟蓟马、棕榈蓟马和苜蓿蓟马。
异翅亚目:例如扁盾蝽属、棉红蝽(Dysdercus intermedius)、方背皮蝽、温带臭虫、长红猎蝽和椎猎蝽属。
同翅目:例如甘蓝粉虱、甘薯粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶镳隐瘤蚜、豆卫矛蚜、苹果蚜、苹果绵蚜、桃大尾蚜、葡萄根瘤蚜、瘿绵蚜属、麦长管蚜、瘤蚜属、忽布疣蚜、禾谷缢管蚜、绿小叶蝉属、殃叶蝉(Euscelis bilobatus)、黑尾叶蝉、欧果坚球蚧、榄珠蜡蚧、灰飞虱、褐飞虱、红肾圆盾蚧、常春藤圆盾蚧、粉蚧属和木虱属。鳞翅目:例如棉红铃虫、松粉蝶尺蛾、果园秋尺蛾、潜叶细蛾(Lithocolletis blancardella)、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜蛾(Bucculatrix thurberiella)、柑橘潜叶蛾、地夜蛾属、切夜蛾属、脏切夜蛾、埃及钻夜蛾、实夜蛾属、甘蓝夜蛾、小眼夜蛾、灰翅夜蛾属、粉纹夜蛾、苹果蠹蛾、粉蝶属、禾草螟属、玉米螟、地中海粉斑螟、蜡螟、幕谷蛾、袋谷蛾、褐织蛾、黄尾卷叶蛾、烟卷蛾(Capua reticulana)、云杉色卷蛾、葡萄果蠹蛾、茶长卷蛾、栎绿卷蛾、Cnaphalocerus属、和水稻负泥虫。
鞘翅目:例如家具窃蠹、谷蠹、豆象(Bruchidius obtectus)、菜豆象、北美家天牛、蓝毛臀萤叶甲、马铃薯叶甲、辣根猿叶甲、条叶甲属、油菜金头跳甲、墨西哥豆瓢虫、隐食甲属、锯谷盗、花象属、米象属、葡萄黑耳喙象、香蕉根颈象、种子象、紫苜蓿叶象、皮蠹属、斑皮蠹属、圆皮蠹属、毛皮蠹属、粉蠹属、油菜花露尾甲、蛛甲属、黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、宽胸叩甲属、五月鳃金龟、马铃薯鳃金龟、褐新西兰肋翅鳃角金龟和稻水象。
膜翅目:例如松叶蜂属、实叶蜂属、毛蚁属、小家蚁和胡蜂属。
双翅目:例如伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厕蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、螫蝇属、狂蝇属、皮蝇属、虻属、螗蜩属(Tannia spp.)、花园毛蚊、瑞典麦杆蝇、草种蝇属、菠菜泉蝇、地中海实蝇、油橄榄果实蝇、沼泽大蚊、种蝇属和斑潜蝇属。
蚤目:例如印鼠客蚤和角叶蚤属。
蛛形纲:例如蝎(Scorpio maurus)、红斑蛛、粗脚粉螨、锐缘蜱属、纯缘蜱属、鸡皮刺螨、兔瘿螨、柑橘皱叶刺瘿螨、牛蜱属、扇头蜱属、花蜱属、璃眼蜱属、硬蜱属、瘙螨属、痒螨属、疥螨属、跗线螨属、苜蓿苔螨、全爪螨属、叶螨属、半跗线螨属和短须螨属。
植物寄生线虫包括例如短体线虫属、相似穿孔线虫、起绒草茎线虫、半穿刺线虫、异皮属、球异皮属、根结属、滑刃线虫属、长针线虫属、剑线属、毛刺属和伞滑刃线虫属。
本发明化合物在一定的浓度或用量下还可任选用作除草剂和杀微生物剂,例如用作杀真菌剂、抗霉菌剂和杀细菌剂。还可以任选作为合成其它活性化合物的中间体或前体。
可将本发明活性化合物转化成常规制剂,例如溶液、乳剂、可润湿粉剂、悬浮剂、粉剂、撒粉剂、糊剂、可溶性粉剂、粒剂、悬浮剂-乳剂浓缩物、浸渍活性化合物的天然或合成物质以及在聚合物中的微囊。
这些制剂可通过已知方法制得,例如通过将活性化合物与增容剂即液体溶剂和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或泡沫形成剂来制得。
如果所用的增容剂是水,还可以使用有机溶剂作为辅助溶剂。合适的液体溶剂主要有:芳族溶剂例如二甲苯、甲苯或烷基萘,氯代芳烃和氯代脂族烃例如氯苯、氯乙烯或二氯甲烷,脂族烃例如环己烷或石蜡如石油馏分,矿物油和植物油,醇例如丁醇或乙二醇,及其醚和酯,酮例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂例如二甲基甲酰胺和二甲亚砜,和水。
合适的固体载体有:例如铵盐和天然矿物粉,例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土,和合成矿物粉例如细分散的二氧化硅、矾土和硅酸盐;适用于粒剂的固体载体有:例如粉碎或分级的天然岩石,例如方解石、大理石、浮石、海泡石、白云石,和合成的无机和有机粗粉颗粒及有机材料颗粒例如锯屑、椰壳、玉米棒碎块、烟草茎;合适的乳化剂和/或泡沫形成剂有:例如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐和蛋白水解产物;合适的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
可在制剂中使用粘结剂,例如羧甲基纤维素、天然和合成粉末、颗粒或胶乳形式的聚合物,例如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂例如脑磷脂和卵磷脂,以及合成磷脂。其它合适的添加剂是矿物油和植物油。
还可以使用着色剂,例如无机颜料如铁氧化物、钛氧化物、普鲁士蓝,和有机染料例如茜素染料、偶氮染料和金属酞菁染料,和微量营养素例如铁、锰、硼、铜、钴、钼和锌的盐。
制剂一般含有0.1-95重量%的活性化合物、优选0.5-90重量%的活性化合物。
本发明活性化合物可以其市售制剂和由上述制剂制备的应用形式与其它活性化合物的混合物的形式存在,其它活性化合物有例如杀虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯类、羧酸酯类、卤代烃类、苯基脲类、和从微生物中产生的物质。
特别令人满意的混合组分的实例如下:
杀真菌剂:
Aldimorph,氨丙膦酸、氨丙膦酸钾、Andoprim、敌菌灵、戊环唑、腈嘧菌酯
苯霜灵、麦锈灵、苯菌灵、苄烯酸、苄烯酸-异丁酯、双丙氨酰膦、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌素、磺嘧菌灵、粉病定,
石硫合剂、Capsimycin、敌菌丹、克菌丹、多菌灵、萎锈灵、Carvon、灭螨锰、灭瘟唑、苯咪唑菌、地茂散、氯化苦、百菌清、乙菌利、Clozylacon、硫杂灵、清菌脲、环唑醇、环丙嘧啶、酯菌胺,
双乙氧咪唑威、双氯酚、苄氯三唑醇、Diclofluanid、哒菌清、氯硝胺、乙霉威、噁醚唑、甲菌定、烯酰吗啉、烯唑醇、烯唑醇-M、敌螨普、二苯胺、吡菌硫、灭菌磷、二噻农、吗菌灵、多果定、敌菌酮,
克瘟散、氧唑菌、乙环唑、乙菌定、氯唑灵,
噁唑酮菌、菌拿灵、异嘧菌醇、腈苯唑、呋菌胺、种衣酯、拌种咯、苯锈定、丁苯吗啉、薯瘟锡、毒菌锡、福美铁、嘧菌腙、氟定胺、氟联苯菌(Flumetover)、氟菌安、喹唑菌酮、调嘧醇、氟硅唑,磺菌胺、氟酰胺、粉唑胺、灭菌丹、藻菌磷(Fosetyl-Aluminium)、藻菌磷(Fosetyl-Natrium)、四氯苯酞、麦穗宁、呋氨丙灵、呋吡唑灵、灭菌安(Furcarbonil)、呋菌唑、呋醚唑、拌种胺,
双胍辛醋酸酯,
六氯苯、己唑醇、噁霉灵,
烯菌灵、酰胺唑、双胍辛(Iminoctadin)、双胍辛对十二烷基苯磺酸盐(Iminoctadinealbesilate)、双胍辛醋酸盐、Iodocarb、环戊唑醇、异稻瘟腈(IBP)、异丙定、Irumamycin、富士一号、氯苯咪菌酮,
春雷霉素、亚胺菌、铜制品,如,氢氧化铜、环烷酸铜、氯氧化铜、硫酸铜、氧化铜、喹啉铜、和碱式硫酸铜混合物,
锰铜混剂、代森锰锌、代森锰、Meferimzone、嘧菌胺、丙氧灭锈胺、甲霜灵、
环戊唑菌、磺菌威、甲呋菌胺、代森联、苯吡洛菌(Metomeclam)、Metsulfovax、米多霉素、腈菌唑、甲菌利。
福美镍、异丙消、氟苯嘧啶醇,
甲呋酰胺、噁霜灵、Oxamocarb、喹菌酮、氧化萎锈灵(Oxycarboxim)、Oxyfenthiin,
多效唑、稻瘟酯、戊菌唑、戊菌隆、双氯苯磷、多马霉素、粉病灵、多氧霉素、Ployoxorim、噻菌灵、丙氯灵、杀菌利、百维灵、Propanosine-Natrium、丙环唑、甲基代森锌、定菌磷、啶斑肟、二甲嘧菌胺、咯喹酮、氯吡呋醚,
唑喹菌酮、五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇、叶枯酞、四氯硝基苯、调环烯、氟醚唑、涕必灵、噻菌腈、溴氟唑菌、甲基托布津、福美双、硫氰苯甲酰胺、甲基立枯磷、对甲抑菌灵、三唑酮、菌唑醇、叶锈特、唑菌嗪、杨菌胺、三环唑、克啉菌、氟菌唑、嗪氨灵、戊叉唑菌,
烯效唑,
有效霉素、烯菌酮、烯霜苄唑,
氰菌胺、代森锌、福美锌及
咪草酯G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基)-氨基甲酸-1-异丙基酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇(pyrrolidinol),
2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-甲酰苯胺(carboxanilid),
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基环丙烷甲酰胺,
2,6-二氯-5-(甲基硫基)-4-嘧啶基硫氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)-磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-去氧-4-O-(4-O-甲基-β-3-D-吡喃葡糖苷基)-a-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴甲基)-戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺
2-氯-N-(2,6-二甲基苯基-N-(异硫氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲胺,
8-羟基喹啉硫酸盐,
9H-呫吨-9-甲酸-2-[(苯基氨基)-羰基]-酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二甲酸酯,
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯-4,5-双(2-丙炔基氧基)-苯基]-N′-甲氧基-甲亚氨酰胺(methanimidamid),
N-甲酰基-N-羟基-DL-丙氨酸-钠盐,
O,O-二乙基-[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯(ethylphosphoramidothioat)
O-甲基-S-苯基-苯基丙基硫代氨基磷酸酯,
1,2,3-苯并噻二唑-7-硫代羟酸S-甲酯,
螺[2H]-1-苯并吡喃-2,1′(3′H)-异苯并呋喃]-3′-酮,
4-[3,4-二甲氧基苯基-3-(4-氟苯基)-丙烯酰基氧基]-吗啉
杀菌剂:
溴硝丙二醇、双氯酚、氯定、福美镍、春雷霉素、异噻菌酮、呋喃甲酸、土霉素、噻菌灵、链霉素、叶枯酞、硫酸铜和其它铜制剂.
杀虫剂/杀螨剂/杀线虫剂:
阿维菌素、乙酰甲胺磷、啶虫脒、氟丙菊酯、棉铃威、涕灭威、涕灭砜威、甲体氯氰菊酯(Alphacypermethrin)、甲体氯氰菊酯(Alphamethrin)、双甲脒、齐墩螨素、AZ 60541、艾扎丁、甲基吡噁磷、谷硫磷A、谷硫磷M、三唑锡,
波林杆菌芽孢、Bacilluss phaericus、柯敌克菌、苏金杆菌、Baculoviruses、Beauveria bassiana、Beauveria tenella、噁虫威、丙硫克百威、杀虫磺、苯螨特、β-氟氯氰菊酯、联苯肼酯、联苯菊酯、Bioethanomethrin、生物氯菊酯、BPMC、溴硫磷A、合杀威、噻嗪酮、特嘧硫磷、丁酮威、丁基哒螨灵(Butylpyr idaben)、
硫线磷、甲萘威、克百威、三硫磷、丁硫克百威、杀螟丹、Chloethocarb、氯氧磷、氟唑虫清、毒虫畏、氟啶脲、氯甲硫磷、毒死蜱、毒死蜱M、Chlovaporthrin、Cis-Resmethrin、Cispermethrin、Clocythrin、除线威、四螨嗪、杀螟腈、Cycloprene、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺,
溴氰菊酯、内吸磷M、内吸磷S、甲基内吸磷、丁醚脲、二嗪磷、敌敌畏、除虫脲、乐果、甲基毒虫畏、苯虫醚、乙拌磷、碘酰丁二辛、苯氧炔螨、
Eflusilanate、Emamectin、右旋烯炔菊酯、硫丹、Entomopfthoraspp.、S-氰戊菊酯、乙硫苯威、乙硫磷、灭线磷、醚菊酯、特苯噁唑、乙嘧硫磷,
苯线磷、喹螨醚、苯丁锡、杀螟硫磷、苯硫威、Fenoxacrim、Fenoxycarb、甲氰菊酯、Fenpyrad、Fenpyrithrin、唑螨酯、氰戊菊酯、氟虫腈、啶蜱脲、Flubrocythrinate、氟环脲、氟氰戊菊酯、氟虫脲、Flutenzine、氟胺氰菊酯、地虫硫磷、丁苯硫磷、噻唑磷、Fubfenprox、呋线威,
颗粒层增殖病毒,
特丁苯酰肼、HCH、庚烯磷、氟铃脲、噻螨酮、烯虫乙酯,
吡虫啉、氯唑磷、异柳磷、噁唑磷、齐墩螨素,
氯氟氰菊酯、虱螨脲,
马拉硫磷、灭蚜磷、四聚乙醛、甲胺磷、Metharhiziumanisopliae、Metharhizium flavoviride、杀扑磷、甲硫威、灭多威、甲氧苯酰肼、速灭威、噁虫酮、速灭磷、米尔螨素、久效磷,
二溴磷、烯啶虫胺、硝虫噻嗪、双苯氟脲、核多角体病毒,
氧乐果、杀线威、亚砜磷,
Paecilomyces fumosoroseus、对硫磷A、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、嘧啶磷A、甲基嘧啶磷、丙溴磷、猛杀威、残杀威、丙硫磷、发硫磷、吡蚜酮、吡唑硫磷、反灭虫菊、除虫菊、哒螨灵、pyridathion、嘧螨醚、吡丙醚,
喹硫磷,
Ribavirin,
杀抗松、硫线磷、氟硅菊酯、艾克敌、治螟磷、硫丙磷,
氟胺氰菊酯、双苯酰肼、吡螨胺、嘧丙磷(Tebupirimiphos)、氟苯脲、七氟菊酯、双硫磷、灭虫威、特丁磷、杀虫威、辛体氯氰菊酯、Thiamethoxam、蛾蝇腈、Thiatriphos、硫环杀、硫双威、久效威、敌贝特、溴氯氰菊酯、四溴菊酯、苯螨噻、唑蚜威、三唑磷、Triazuron、Trichlophenidine、敌百虫、杀灵脲、混杀威,
蚜灭磷、氟吡唑虫、麦柯特尔,
YI 5302,
Zeta-cypermethrin、Zolaprofos,
(1R-顺)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)呋喃亚基)-甲基]-2,2-二甲基环丙烷甲酸酯,
2,2,3,3-四甲基环丙烷甲酸[(3-苯氧基苯基)-甲基]酯,
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺,
2-(2-氯-6-氟苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰基氧基)-3-十二烷基-1,4-萘二酮,
2-氯-N-[[[4-(1-苯基乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)-苯基]-氨基]-羰基]苯甲酰胺,
3-甲基苯基-丙基氨基甲酸酯,
4-[4-(4-乙氧基苯基)-4-甲基戊基]-1-氟-2-苯氧基-苯,
4-氯-2-(1,1-二甲基乙基)-5-[[2-(2,6-二甲基-4-苯氧基苯氧基)乙基]硫基]-3(2H)-哒嗪酮,
4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮,
4-氯-5-[(6-氯-3-吡啶基)甲氧基]-2-(3,4-二氯苯基)-3(2H)哒嗪酮,
苏云金杆菌菌株EG-2348,
苯甲酸[2-苯甲酰基-1-(1,1-二甲基乙基)-酰肼,
丁酸[2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4.5]癸-3-烯-4-基]酯,
[3-[(6-氯-3-吡啶基)甲基]-2-噻唑烷亚基]-氨基氰,
二氢-2-(硝基亚甲基)-2H-1,3-噻嗪-3(4H)-甲醛,
[2-[[1,6-二氢-6-氧代-1-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯,
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸,
N-(4-氯苯基)-3-[4-(二氟甲氧基)苯基]-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺,
N-[(2-氯-5-噻唑基)甲基]-N′-甲基-N″-硝基-胍,
N-甲基-N′-(1-甲基-2-丙烯基)-1,2-肼二硫代甲酰胺,
N-甲基-N′-2-丙烯基-1,2-肼二硫代甲酰胺,
O,O-二乙基-[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯。
N-氰基甲基-4-三氟甲基烟酰胺
3,5-二氯-1-(3,3-二氯-2-丙烯基氧基)-4-[3-(5-三氟甲基吡啶-2-基氧基)-丙氧基]-苯
与其它已知活性化合物例如除草剂或肥料以及生长调节剂的混合物也是可能的。
当用作杀虫剂时,本发明活性化合物可以以其市售制剂和由上述制剂制备的应用形式与增效剂的混合物的形式存在。增效剂是能够增加活性化合物活性的化合物,但加入的增效剂本身不是必须有活性。
由市售制剂制备的应用形式中活性化合物的含量可以在很宽的范围内变化。使用形式中活性化合物的浓度为0.0000001-95重量%、优选0.0001-1重量%。
以适用于应用形式的常规方法进行使用。
当用于防治卫生害虫和储藏物品中的害虫时,活性化合物具有优良的木材和粘土残留活性以及对刷石灰的基底具有很好的碱稳定性。
本发明活性化合物不仅对植物害虫、卫生害虫和储藏物品中的害虫具有活性,而且在兽医领域,对防治动物寄生虫(外寄生虫)也有活性,该寄生虫为例如硬蜱、软蜱、兽疥癣螨、叶螨、蝇(叮咬和吸食)、寄生性蝇幼虫、虱、头虱、羽虱和跳蚤。这些寄生虫包括:
虱目,例如血虱属、颚虱属、虱属、Phtirus spp.、管虱属。
食毛目以及钝角亚目和细角亚目,例如毛羽虱属、Menopon spp.、巨毛虱属、羽虱属、Werneckiella spp.、Lepikentron spp.、畜虱属、嚼虱属、猫羽虱属。
双翅目以及长角亚目和短角亚目,例如伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、Lutzomyia spp.、库蠓属、斑虻属、瘤虻属、黄虻属、虻属、麻翅虻属、Philipomyia spp.、蜂虱蝇属、家蝇属、齿股蝇属、螫蝇属、角蝇属、莫蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、Wohlfahrtia spp.、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、Lipoptena spp.、蜱蝇属。
蚤目,例如蚤属、栉首蚤属、印鼠客蚤属、角叶蚤属。
异翅亚目,例如臭虫属、椎猎蝽属、红腹猎蝽属、全圆蝽属。
蜚蠊目,例如东方蜚蠊、美洲大蠊、德国小蠊、蜚蠊属。
蜱螨目以及后气门亚目和中气门亚目,例如锐缘蜱属、纯缘蜱属、残喙蜱属、硬蜱属、花蜱属、牛蜱属、革蜱属、Haemophysalis spp.、璃眼蜱属、扇头蜱属、皮刺螨属、刺利螨属、肺刺螨属、胸孔螨属和瓦螨属。
辐螨亚目(前气门亚目)和粉螨目(无气门亚目),例如蜂跗线螨属、姬螫螨属、禽螫厘螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、瘙螨属、痒螨属、耳螨属、疥螨属、痂螨属、疙螨属、胞螨属和皮膜螨属。
本发明活性化合物也适用于控制侵扰农业家畜例如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂,其它家养动物例如狗、猫、笼养鸟和水族馆的鱼,以及所谓的试验动物例如田鼠、豚鼠、大鼠和小鼠的节肢动物。通过控制上述节肢动物,旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等),因此,通过使用本发明的活性化合物可以使畜牧业更经济、更简单。
应用于兽医领域时,本发明活性化合物可通过已知方法给药,即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、喂食过程、栓剂形式进行;非经肠给药,例如通过注射(肌内注射、皮下注射、静脉注射、腹膜内注射等)、植入法给药;经鼻给药;经皮肤给药,例如以浸泡或洗浴、喷雾、泼上或擦上、洗涤和撒粉方式进行,也可借助于含有活性化合物的成型制品例如项圈、耳饰物、尾饰物、肢环(带)、笼头、标志器具等给药。
当用于家畜、家禽、宠物等时,本发明活性化合物可使用制剂形式(例如粉剂、乳剂、能流动组合物),其中包含1-80重量%的活性化合物,直接使用或者稀释100-10000倍后使用,或者用作药浴。
另外发现本发明活性化合物还对损坏工业材料的昆虫具有很强的杀虫活性。
作为实例并优选列出下列昆虫,但并不限于此:
鞘翅目昆虫,例如北美家天牛、绿虎天牛(Chlorophoruspilosis)、家具窃蠹、报死材窃蠹、类翼窃蠹、Dendrobium pertinex、松芽枝窃蠹、松产品窃蠹(Priobium carpini)、褐粉蠹、粉蠹(Lyctusafricanus)、南方粉蠹、栎粉蠹、粉蠹(Lyctus pubescens)、胸粉蠹(Trogoxylon aequale)、鳞毛粉蠹、材小蠹属、条木小蠹属、咖啡黑长蠹、Bostrychus capucins、褐异翅长蠹、棘长蠹属、竹竿粉长蠹。
膜翅目,例如蓝黑树蜂、云杉大树蜂、泰加大树蜂、大树蜂(Urocerus augur)。
白蚁,例如木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁、印巴结构木异白蚁、欧美散白蚁、散白蚁(Reticulitermessantonensis)、散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁、内华达古白蚁、台湾乳白蚁。
缨尾目,例如台湾衣鱼。
在本文中,工业材料可理解为表示无生命材料,例如优选合成材料、胶粘剂、胶水、纸和板、皮革、木材、加工后的木制品和涂料。
木材以及加工后的木制品是非常特别优选需要保护以免受昆虫侵袭的材料。
可通过本发明组合物或含有本发明组合物的混合物保护的木材和加工后的木制品可以理解为表示,例如:建筑用木材、木梁、铁路轨枕、桥梁组件、桥形码头、木制交通工具、箱子、货架、集装箱、电线杆、木镶板、木窗和木门、胶合板、粗纸板、在房屋建筑或建筑细木工行业中常用的细木工或木制品。
活性化合物可直接使用,或者以浓缩形式或常规制剂例如粉剂、颗粒剂、溶液、悬浮液、乳剂或糊剂方式使用。
上述制剂可以以本身已知的方法制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、抗水剂混合,任选加入催干剂和UV稳定剂,以及任选加入染料和颜料和其它加工助剂。
用于保护木材和建筑木材制品的杀虫组合物或浓缩物包含0.0001-95重量%、特别是0.001-60重量%的本发明活性化合物。
组合物或浓缩物的使用量是根据昆虫的种类、存在及介质情况而确定的。最佳施用量分别可通过系列试验确定。然而,按照需保护的材料的重量计,一般使用0.0001-20重量%、优选0.001-10重量%的活性化合物是足够的。
合适的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性油性或油类有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水,以及任选加入乳化剂和/或润湿剂。
优选使用的有机化学溶剂是蒸发值大于35以及闪点大于30℃、优选大于45℃的油性或油类溶剂。适合的用作这类低挥发度的、不溶于水的油性和油类溶剂物质是相应的矿物油或其芳族馏份,或含有矿物油的溶剂混合物,优选石油溶剂、石油和/或烷基苯。
优选使用沸程为170-200℃的矿物油,沸程为170-220℃的石油溶剂,沸程为250-350℃的锭子油,沸程为160-280℃的石油或芳烃,以及松节油等。
在优选实施方案中,使用沸程为180-210℃的液体脂肪烃或沸程为180-220℃的芳族和脂族烃的高沸点混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
蒸发值大于35以及闪点大于30℃、优选大于45℃的低挥发性有机油性或油类溶剂可被易挥发或中挥发度的有机溶剂部分地替换,条件是溶剂混合物的蒸发值同样大于35,且闪点大于30℃、并优选大于45℃,以及杀虫剂/杀菌剂混合物可溶或可乳化于该溶剂混合物中。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物被脂族极性有机化学溶剂或溶剂混合物替代。优选使用含有羟基和/或酯和/或醚基的脂族有机化学溶剂,例如乙二醇醚、酯等。
本发明使用的有机化学粘合剂是本身已知的合成树脂和/或已知的粘合干性油,它们可用水稀释和/或可溶解或分散或乳化于上述使用的有机化学溶剂中,特别是由下列物质组成或包含下列物质的粘合剂:丙烯酸树脂,乙烯基树脂例如聚乙酸乙烯酯,聚酯树脂,缩聚树脂或加聚树脂,聚氨酯树脂,醇酸树脂或改性的醇酸树脂,酚树脂,烃类树脂,如茚/香豆酮树脂,硅树脂,干性植物油和/或干性油和/或基于天然和/或合成树脂的物理干性粘合剂。
用作粘合剂的合成树脂可以以乳剂、分散剂或溶液的形式使用。沥青或沥青状物质也可用作粘合剂,用量最高达10重量%。还可以使用本身已知的染料、颜料、防水剂、气味掩蔽剂、和抑制剂或防腐剂等。
依据本发明,组合物或浓缩物优选包含至少一种醇酸树脂或改性醇酸树脂和/或一种干性植物油作为有机化学粘合剂。本发明优选使用含油量大于45重量%、优选为50-68重量%的醇酸树脂。
上述粘合剂可全部或部分地被固定剂(混合物)或增塑剂(混合物)替代。加入这些添加剂的目的是防止活性化合物的蒸发以及结晶或沉淀。它们优选替代0.01-30%的粘合剂(按所用的粘合剂为100%计)
增塑剂选自邻苯二甲酸酯类的化学物质例如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯例如磷酸三丁酯,己二酸酯例如己二酸二(2-乙基己基)酯,硬脂酸酯例如硬脂酸丁酯或硬脂酸戊酯,油酸酯例如油酸丁酯,甘油醚或高分子量的乙二醇醚,甘油酯和对甲苯磺酸酯
固定剂在化学上基于聚乙烯基烷基醚例如聚乙烯基甲基醚,或酮类例如二苯甲酮和亚乙基二苯甲酮。
其它合适的溶剂或稀释剂特别是水,任选与一种或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂混合使用。
对木材特别有效的保护是通过工业规模浸渍方法实现的,例如通过真空、二次真空或加压法。
现用型组合物还可以任选包含其它杀虫剂和任选一种或多种杀菌剂。
合适的另外的混合组分优选选自在WO 94/29268中提及的杀虫剂和杀菌剂。将在该文献中提及的化合物明确作为本申请的一组分。
特别优选的混合组分是杀虫剂例如毒死蜱、辛硫磷、氟硅菊酯、顺式氯氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、啶虫脒、氟虫脲、氟铃脲、四氟菊酯、Thiacloprid、Methoxyphenoxid和杀铃脲,以及杀真菌剂例如氧唑菌、己唑醇、氧环唑、丙环唑、戊唑醇、环丙唑醇、叶菌唑、抑霉唑、抑菌灵、甲苯氟磺胺、3-碘-2-丙炔基-丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明的组合也可用于保护与海水或微咸水接触的物体例如船体、筛子、网、建筑物、码头和信号系统免受植被污染。
由于污染了定居性寡毛纲目,如龙介虫科以及甲壳类和Ledamorpha(茗荷儿)类,如各种茗荷属和铠茗荷属,或藤壶亚目(藤壶虫),例如藤壶属或指茗荷属的污染增加了船体的摩擦阻力并由于增加了能源消耗以及由于经常在干船坞上放置而明显增加了运营成本。
除被海藻,例如水云属和仙菜属污染外,特别重要的是由定居性软甲亚纲(昆甲类)的附着侵染,该昆甲类包括在蔓足纲(蔓足类甲壳动物)中。
令人惊奇的是,现在已经发现单独的或者与其它活性化合物联合使用的本发明化合物具有突出的防污作用。
通过使用单独的或者与其它活性化合物联合使用的本发明化合物,使得无需使用重金属,例如硫化二(三烷基锡)、三正丁基月桂酸锡、三正丁基氯化锡、氧化铜(I)、三乙基氯化锡、三正丁基(2-苯基-4-氯苯氧基)锡、三丁基氧化锡、二硫化钼、氧化锑、聚合的钛酸丁酯、氯化苯基-(联吡啶)-铋、三正丁基氟化锡、亚乙基二硫代氨基甲酸锰、二甲基二硫代氨基甲酸锌、亚乙基双硫代氨基甲酸锌、2-吡啶硫醇1-氧化物的锌盐和铜盐、双二甲基二硫代氨基甲酰基亚乙基双硫代氨基甲酸锌、氧化锌、亚乙基双二硫代氨基甲酸铜(I)、硫氰酸铜、环烷酸铜和三丁基卤化锡,或显著降低上述化合物浓度。
即用型防污漆还可任选包括其它活性化合物,优选杀藻剂、杀真菌剂、除草剂、杀软体动物剂或其它防污活性化合物。
与本发明防污组合物联合使用的合适的组分优选为:
杀藻剂,例如
2-叔丁基氨基-4-环丙基氨基-6-甲硫基-1,3,5-三嗪、双氯酚、敌草隆、菌多酸、三苯基醋酸锡、异丙隆、甲基苯噻隆、乙氧氟草醚、灭藻醌和特丁净;
杀真菌剂,例如
苯并[b]噻吩甲酸环己基酰胺S,S-二氧化物、抑菌灵、Fluorfolpet、丁基氨基甲酸3-碘-2-丙炔基酯、甲苯氟磺胺和唑类,例如氧环唑、环丙唑醇、氧唑菌、己唑醇、叶菌唑、丙环唑和戊唑醇;
杀软体动物剂,例如
醋酸三苯基锡、四聚乙醛、甲硫威、杀螺胺、硫双威和混杀威;
或常用的防污活性化合物,例如
4,5-二氯-2-辛基-4-异噻唑啉-3-酮,Diiodmethylparatrylsulfon,2-(N,N-二甲硫基氨基甲酰基硫代)-5-硝基噻唑烷,2-吡啶硫醇1-氧化物的钾盐、铜盐、钠盐和锌盐,吡啶三苯基硼烷、四丁基二锡氧烷、2,3,5,6-四氯-4-(甲基磺酰基)-吡啶、2,4,5,6-四氯间苯二氰、二硫化四甲基秋兰姆和2,4,6-三氯苯基马来酰亚胺。
所用的防污组合物中包含浓度为0.001-50重量%、特别是0.01-20重量%的本发明活性化合物。
此外,本发明防污组合物还包含常用组分,例如在Ungerer,Chem.Ind.1985,37,730-732和Williams,Antifouling MarineCoatings,Noyes,Park Ridge,1973中描述的常用组分。
除了杀藻、杀真菌、杀软体动物活性化合物和本发明杀虫活性化合物以外,防污涂料还特别包含粘合剂。
公知的粘合剂的实例包括溶剂体系中的聚氯乙烯、溶剂体系中的氯化橡胶、溶剂体系特别是含水体系中的丙烯酸类树脂、水分散体形式或有机溶剂体系形式的氯乙烯/醋酸乙烯酯共聚物体系、丁二烯/苯乙烯/丙烯腈橡胶、干性油例如亚麻子油,树脂酯或与焦油或沥青、柏油以及环氧化合物、少量氯化橡胶、氯化聚丙烯和乙烯基树脂混合形成的改性硬树脂。
涂料还任选包含无机颜料、有机颜料或染料,它们优选不溶于海水。涂料还可以包含例如松香类物质,以使活性化合物可控制地释放。此外,涂料中还可以包含增塑剂、影响流变性质的改良剂、以及其它常规组分。还可以将本发明化合物或上述混合物加入自抛光防污体系中。
本发明活性化合物还适于控制封闭空间例如公寓、厂房、办公室、车厢等空间中出现的动物害虫,特别是昆虫、蜘蛛和螨。它们可单独使用或者与家用杀昆虫产品中的其它活性化合物和助剂联合使用以控制害虫。它们对敏感和抗性种群以及所有发育阶段都有杀虫活性。这些害虫包括:
蝎目,例如钳蝎(Buthus occitanus)。
蜱螨目,例如波斯锐缘蜱、翘缘锐缘蜱、苔螨属、鸡皮刺螨、家食甜螨、非洲钝缘蜱、血红扇头蜱、恙螨(Trombicula alfreddugesi)、Neutrombicula autumnalis、屋尘螨、粉尘螨。
蛛形目,例如鸟蛤蛛科、园蛛科。
盲蛛目,例如拟蝎类(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、Opiliones phalangium。
等足目,例如潮虫、鼠妇。
倍足目,例如具斑马陆、山蛩虫属。
唇足目,例如地蜈蚣属。
Zygentoma目,例如栉衣鱼属、台湾衣鱼、Lepismodesinquilinus。
蜚蠊目,例如东方蜚蠊、德国小蠊、小蠊属(Blattellaasahinai)、马得拉蜚蠊、角腹蠊属、木蠊属、澳洲大蠊、美洲大蠊、褐斑大蠊、黑胸大蠊、长须蜚蠊。
跳跃亚目,例如家蟀。
革翅目,例如欧洲球螋。
等翅目,例如木白蚁属、散白蚁属。
啮虫目,例如Lepinatus属、粉啮虫属。
鞘翅目,例如圆皮蠹属、毛皮蠹属、长头谷蠹属、隐跗郭公虫属、蛛甲属、谷蠹、谷象、米象、玉米象、药材甲。
双翅目,例如埃及伊蚊、白纹伊蚊、Aedes taeniorhynchus、按蚊属、红头丽蝇、高额麻虻、致倦库蚊、尖音库蚊、Culex tarsalis、果蝇属、夏厕蝇、家蝇、白蛉属、麻蝇(Sarcophaga carnaria)、蚋属、厩螫蝇、大蚊(Tipula paludosa)。
鳞翅目,例如小蜡螟、蜡螟、印度古斑螟、谷蛾、袋谷蛾、幕谷蛾。
蚤目,例如犬栉首蚤、猫栉首蚤指名亚种、人蚤、穿皮潜蚤、印鼠客蚤。
膜翅目,例如广布弓背蚁、亮毛蚁、黑毛蚁、Lasius umbratus、小家蚁、Paravespula属、铺道蚁。
虱目,例如头虱、体虱、阴虱。
异翅亚目,例如热带臭虫、温带臭虫、长红猎蝽、侵扰锥猎蝽。
在家用杀虫剂领域中,本发明化合物可单独使用或者与其它合适的活性化合物混合使用,所述其它合适的活性化合物有例如磷酸酯类、氨基甲酸酯类、拟除虫菊酯类,生长调节剂或选自其它已知各类杀虫剂的活性化合物。
可以如下形式使用:气溶胶形式,非增压喷雾,例如泵、雾化器、烟雾发生器、自动成雾系统、成雾器、泡沫、凝胶、带有由纤维素或合成材料制成的汽化片的蒸发器、液体蒸发器、凝胶和薄膜蒸发器、推进式蒸发器、不需能量或被动式蒸发系统、防蛀纸、防蛀袋和防蛀胶、作为颗粒剂或粉剂撒布饵料中或在饵料位置。
本发明活性化合物可用作脱叶剂、干燥剂、植物杀死剂、和尤其是除草剂。所谓杂草,从最广义上来讲,应理解为在不需要它们的地方生长的所有植物。本发明化合物是起广谱除草剂作用还是起选择性除草剂作用基本上取决于其用量。
本发明活性化合物可用于例如下述植物:
以下各属的双子叶杂草:苘麻属、苋属、豕草属、单花葵属、春黄菊属、Aphanes、滨藜属、雏菊属、鬼针草属、荠属、飞廉属、决明属、矢车菊属、藜属、蓟属、旋花属、曼陀罗属、金钱草属、刺酸模属、糖芥属、大戟属、鼬瓣花属、牛膝菊属、猪殃殃属、木槿属、番薯属、地肤属、夜芝麻属、独行菜属、母草属、母菊属、薄荷属、山靛属、羊鱼属(Mullugo)、勿忘草属、罂粟属、牵牛属、车前属、蓼属、马齿苋属、毛茛属、萝卜属、焊菜属、水松叶属、酸模属、猪毛菜属、千里光属、田菁属、黄花稔属、芸苔属、茄属、苦苣菜属、尖瓣花属、繁缕属、蒲公英属、遏蓝菜属、三叶草属、荨麻属、婆婆纳属、堇菜属、苍耳属。
以下各属的双子叶农作物:落花生属、甜菜属、芥属、黄瓜属、南瓜属、向日葵属、胡萝卜属、大豆属、棉属、番薯属、莴苣属、亚麻属、番茄属、烟草属、菜豆属、豌豆属、茄属、野豌豆属。
以下各属的单子叶杂草:山羊草属、冰草属、翦股颖属、看麦娘属、假翦股颍属、燕麦属、臂形草属、雀麦属、蒺藜草属、鸭跖草属、狗牙根属、莎草属、龙爪茅属、马唐属、稗属、荸荠属、蟀蟋草属、画眉草属、野黍属、羊茅属、飘拂草属、异蕊花属、白矛属、鸭嘴草属、千斤子属、毒麦属、雨久花属、黍属、雀稗属、鹃草属、梯牧草属、早熟禾属、筒轴茅属、慈菇属、厂草属、狗尾草属、蜀黍属。
以下各属的单子叶农作物:葱属、菠罗属、天门冬属、燕麦属、大麦属、稻属、黍属、甘蔗属、黑麦属、高梁属、黑小麦属、小麦属、玉蜀黍属。
然而,本发明活性化合物的应用决不限于这些属的植物,还可以以相同方式延伸到其它植物。
根据浓度,本发明活性化合物适于控制例如工业场地和铁路轨道,以及有和没有树木生长的道路和场院的所有杂草。同样,本发明活性化合物可用于控制多年生农作物例如森林、观赏林、果园、葡萄园、柑桔园、坚果园、香蕉林、咖啡园、茶叶种植园、橡胶种植园、油棕榈种植园、可可种植园、浆果种植园和蛇麻草田中的杂草,以及控制草坪、草地以及牧场中的杂草,和用于选择性地控制一年生长农作物中的杂草。
当用于土壤和地面上的植物部分时,本发明化合物具有强的除草活性和广的活性作用谱。在一定程度上,它们还适于在单子叶农作物和双子叶农作物中通过芽前和芽后法选择性地控制单子叶和双子叶杂草。
以一定浓度或施用量,本发明活性化合物还可用于控制动物害虫和真菌或细菌性植物疾病。它们还可任选用作合成其它活性化合物的中间体或前体。
根据本发明,可以处理所有植物和植物各部分。此处植物可以理解为所有植物以及植物群落,如需要和不需要的野生植物或农作物(包括自然长出的农作物)。农作物可以是通过常规植物育种和优化方法或通过生物技术和重组方法或上述方法的结合获得的植物,包括转基因植物以及包括可获得或不能获得植物品种保护的植物品种。植物的部分应理解为植物的所有地面上和地面下部分器官,如茎、叶、花和根,可提及的实例为叶片、针叶、叶柄、树干、花、子实体、果实、种子、根、块茎和根状茎。植物各部分还包括收获材料以及无性和有性繁殖材料,例如插条、块茎、根状茎、压枝和种子。
采用活性化合物进行植物和植物各部分的本发明处理方法是通过常规处理方法直接施用或将化合物作用于它们的环境、生境或贮藏区进行处理,例如浸渍、喷雾、熏蒸、弥雾、撒播、刷涂以及在繁殖材料特别是种子的情况下还可以进行一层或多层包衣。
如上所提及,可按照本发明处理所有植物及其各部分。在一个优选的实施方案中,处理已有的或通过常规的生物育种方法,如杂交或原生质体融合得到的植物种类和植物品种和其各部分。在另一个优选的实施方案中,处理通过基因工程方法,任选与常规方法联合(基因修饰生物体)得到的转基因植物和植物品种及其各部分。术语“各部分”或“植物的各部分”或“植物部分”在上面已作过解释。
按照本发明,特别优选处理在各种情况下市售可得的或在使用的植物品种的植物。植物品种应理解为表示具有一定特征(“特性”),并且已通过常规育种、通过诱变或通过重组DNA技术获得的植物。它们可以是品种型、生物属型或基因型。
根据植物种类或植物品种、它们的栖息地和生长条件(土壤、气候、植物生长期、营养),按照本发明的处理方法还可导致超加和的(“协同”)作用。因此,例如,可减少用量和/或拓宽活性谱和/或提高本发明所用的物质和组合物的活性、改善植物生长、增强对高或低温的耐受性、增强对旱灾或水灾或土壤盐量的耐受性、增加花卉的性能、易于收获、加速成熟、提高收获量、提高收获产品的质量和/或提高产品的营养价值、提高产品的储存稳定性和/或可加工性,这些超出了本身所期望的效果。
属于按照本发明优选进行处理的转基因植物或植物品种(即通过基因工程得到的那些)包括通过基因材料的基因工程修饰得到的所有植物,所述基因修饰赋予这些植物特别有利的有用的性能(“特性”)。这种性能的例子是较好的植物生长、增强对高或低温的耐受性、增强对旱灾或水灾或土壤盐量的耐受性、增加花卉的性能、易于收获、加速成熟、较高的收获产量、收获产品较好的质量和/或较高的营养价值、收获产品较好的储存稳定性和/或可加工性。进一步和特别强调的所述性能的例子是提高植物对动物和微生物的害虫,如昆虫、螨、植物病菌真菌、细菌和/或病毒的抵御性,以及提高植物对某些除草活性化合物的耐受性。可提及的转基因植物的例子是重要的农作物植物,如谷类植物(小麦、稻)、玉米、大豆、土豆、棉花、油菜籽油菜和水果植物(水果为苹果、梨、柑橘属水果和葡萄),特别强调的是玉米、大豆、土豆、棉花和油菜籽油菜。特别强调的特性是通过在植物中产生的毒素,特别是通过来自Thuringiensis杆菌的基因物质(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及它们的联合)(下文称作“Bt植物”)在植物中产生的那些增强植物对昆虫的抵御。还特别需要强调的特性是提高通过系统获得的抗性(SAR)、系统素(Systemin)、植物抗毒素、Elicitoren和抗性基因以及相应表达的蛋白和毒素来抗真菌、细菌和毒素的植物防护作用。此外,特别强调的特性是提高植物对某些除草活性化合物,如咪唑啉酮类、磺酰脲类、草甘膦类或膦基麦黄酮(例如“PAT”基因)的耐受性。给予所述的需要的特性的基因也可以在转基因植物中相互联合存在。可提及的“Bt植物”的例子是以商标名YIELDGARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和Newleaf(土豆)出售的玉米品种、棉花品种、大豆品种和土豆品种。可提及的耐受除草剂的植物是以商标名Roundup Ready(耐受草甘膦,例如玉米、棉花、大豆)、Liberty Link(耐受膦基麦黄酮,例如油菜籽油菜)、IMI(耐受咪唑啉酮类)和STS(耐受磺酰脲类,例如玉米)出售的玉米品种、棉花品种、大豆品种。可提及的耐除草剂的植物(以常规方式除草剂耐受育种)包括以商标名Clearfield(例如玉米)出售的品种。当然,这些叙述也适用于具有所述特性或将来改良的基因特性的将来开发的植物或将来投放市场的植物品种。
所列出的植物可以以特别有利的方式用式(I)化合物依据本发明进行处理。上述关于活性化合物的优选范围也适用于这些植物的处理。特别需要强调的是用在本文中特别提及的混合物处理植物。
可将本发明活性化合物转化成常规制剂,例如溶液、乳剂、可润湿粉剂、悬浮剂、粉剂、撒粉剂、糊剂、可溶性粉剂、粒剂、悬浮剂-乳剂浓缩物、浸渍活性化合物的天然或合成物质、和在聚合物中的微囊。
这些制剂可通过已知方法制得,例如通过将活性化合物与增容剂即液体溶剂和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或泡沫形成剂来制得。
如果所用的增容剂是水,还可以使用有机溶剂作为辅助溶剂。合适的液体溶剂主要有:芳族溶剂例如二甲苯、甲苯或烷基萘,氯代芳族烃和氯代脂族烃例如氯苯、氯乙烯或二氯甲烷,脂族烃例如环己烷或石蜡如石油馏分,矿物油和植物油,醇类例如丁醇或二醇,及其醚和酯,酮类例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂例如二甲基甲酰胺和二甲亚砜,和水。
合适的固体载体有:例如铵盐和天然岩石粉,例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土,和合成岩石粉例如细分散的二氧化硅、矾土和硅酸盐;适用于粒剂的固体载体有:例如粉碎或分级的天然岩石,例如方解石、大理石、浮石、海泡石、白云石,和合成的无机和有机粗粉颗粒例如锯屑、椰壳、玉米棒碎块、烟草茎;合适的乳化剂和/或泡沫形成剂有:例如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚例如烷基芳基聚二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐和蛋白水解产物;合适的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
可在制剂中使用粘附剂,例如羧甲基纤维素、天然和合成粉末、颗粒或胶乳形式的聚合物例如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂例如脑磷脂和卵磷脂,与合成磷脂。其它合适的添加剂是矿物油和植物油。
还可以使用着色剂,例如无机颜料如氧化铁、氧化钛、普鲁士蓝,和有机染料例如茜素染料、偶氮染料和金属酞菁染料,和微量营养素例如铁、锰、硼、铜、钴、钼和锌的盐。
制剂一般含有0.1-95重量%的活性化合物、优选0.5-90重量%的活性化合物。
为了控制杂草,以自身的形式或者在其制剂中的本发明活性化合物还可以与已知除草剂和/或改善农作物相容性的物质(“安全剂”)的混合物使用,对此成品制剂或罐装混合物都是可行的。与包含一种或多种已知除草剂和安全剂的除草剂的混合物也是可行的。
对于这些混合物适合的已知除草剂是,例如:乙草胺、氟羧草醚(及钠盐)、苯草醚、甲草胺、枯杀达(及钠盐)、莠灭净、Amicarbazone、先甲草胺、磺氨黄隆、莎稗磷、黄草灵、莠去津、唑啶炔草、四唑黄隆、BAS-662H、Beflubutamid、草除灵(及其乙酯)、呋草黄、苄嘧磺隆(及其甲酯)、灭草松、Benzfendizone、Benzobicyclon、吡草酮、新燕灵(及其甲酯)、双丙氨酰膦、治草醚、双嘧苯甲酸(及钠盐)、溴丁酰草胺、杀草全、溴苯腈、丁草胺、Butafenacil(-allyl)、丁氧环酮、苏达灭、Cafens trole、醌肟草、长杀草、氟酮唑草(及其乙酯)、氯硝醚、灭草平、杀草敏、氯嘧磺隆(及其乙酯)、草枯醚、氯磺隆、氯麦隆、Cinidon(-ethyl)、环庚草醚、醚磺隆、Clefoxydim、烯草酮、炔草酯、异恶草酮、稗草胺、二氯吡啶酸、Clopyrasulfuron(-methyl)、唑嘧磺胺盐、Cumyluron、草净津、Cybutryne、草灭特、环丙磺隆、噻草酮、氰氟草酯、2,4-D、2,4-DB、异苯敌草、燕麦敌、麦草畏、2,4-滴丙酸(高2,4-滴丙酸)、禾草灵、唑嘧磺胺、安塔(及其乙酯)、野燕枯、吡氟草胺、二氟吡隆、丁噁隆、哌草丹、克草胺、戊草津、噻吩草胺、Dimexyflam、敌乐胺、草乃敌、敌草快、氟硫草定、敌草隆、香草隆、Epropodan、EPTC、禾草畏、丁氟消草、胺苯磺隆、乙呋草黄、Ethoxyfen、乙氧嘧磺隆、Etobenzanid、噁唑禾草灵(高噁唑禾草灵)、Fentrazamide、氟燕灵(异丙基、异丙基-L、甲基酯)、啶嘧磺隆、氟鼠灵、吡氟禾草灵(精吡氟禾草灵)、Fluazolate、Flucarbazone(-sodium)、Flufenacet、氟唑啶草、酰亚胺苯氧乙酸(及其戊酯)、氟噁嗪酮、Flumipropyn、氟唑啶草、氟草隆、氟咯草酮、乙羧氟草隆(及其乙酯)、胺草唑、Flupropacil、氟啶磺隆、抑草丁、氟草同、氟草烟(及其丁氧异丙酯、氟氯胺啶)、调嘧醇、呋草酮、达草氟、Fluthiamide、氟磺胺草醚、Foramsulfuron、草铵膦、草甘膦(及其异丙基铵)、氟硝磺酰胺、吡氟氯禾灵(及其乙氧基乙酯、-P-甲酯)、六嗪同、咪草酸(及其甲酯)、Imazamethapyr、咪草啶酸、Imazapic、灭草烟、灭草喹、咪草烟、啶咪磺隆、Iodosulfuron(-methyl、-sodium)、碘苯腈、异乐灵、异丙隆、异恶隆、异恶草胺、Isoxachlortole、异恶氟草、恶草醚、乳氟禾草灵、环草啶、利谷隆、2甲4氯、2甲4氯丙酸、苯噻草胺、Mesosulfuron、Mesotrione、苯嗪草、吡草胺、噻唑隆、色满隆、秀谷隆、(α-)异丙甲草胺、唑草磺胺、甲氧隆、赛可津、甲磺隆(及其甲酯)、草达灭、绿谷隆、萘丙胺、草萘胺、草不隆、烟嘧磺隆、达草灭、坪草丹、黄草消、炔丙恶唑草、恶草灵、环丙氧磺隆、氯恶嗪草、乙氧氟草醚、百草枯、壬酸、胺硝草、Pendralin、Pentoxazone、甜菜宁、Picolinafen、哌草磷、丙草胺、氟嘧磺隆(及其甲酯)、Profluazol、扑草净、毒草胺、敌稗、喔草酸、异丙草胺、Procarbazone(-sodium)、拿草特、苄草丹、氟丙磺隆、氟唑草酯、Pyrazogyl、吡唑特、吡嘧磺隆(及其乙酯)、苄草唑、嘧苯草肟、稗草畏、达草止、Pyridatol、Pyriftalid、肟啶草(及其乙酯)、嘧硫苯甲酸(及其钠盐)、二氯喹啉酸、喹草酸、灭藻醌、喹禾灵(精喹禾灵、精喹禾灵四氢糠基酯)、玉嘧磺隆、稀禾啶、西玛津、西草净、磺草酮、磺胺草唑、嘧磺隆(及其甲酯)、草硫膦、乙黄磺隆、丙戊草胺、丁唑隆、Tepraloxydim、特丁津、去草净、噻醚草胺、Thiafluamide、噻氟啶草、噻二唑胺、噻磺隆(及其甲酯)、杀草丹、丁草威、肟草酮、野麦畏、醚苯磺隆、苯磺隆(及其甲酯)、定草、灭草环、氟乐灵、Trifloxysulfuron、氟胺磺隆(酸及其甲酯)、Tritosulfuron。
与其它已知活性化合物例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养素、和改善土壤结构的活性剂的混合物也是可行的。
活性化合物可以以自身的形式使用,以其制剂形式使用,或者在通过进一步稀释由其制得的应用剂型例如即用溶液、悬浮剂、乳剂、粉剂、糊剂和粒剂中使用。它们可通过常规方式例如通过灌溉、喷雾、雾化、或撒布来使用。
本发明活性化合物可在植物发芽之前和之后施用。可在播种前将本发明活性化合物掺入到土壤中。
活性化合物的用量可在较宽的范围内变化。其用量基本上取决于所需效果的性质。其用量一般为1g-10kg活性化合物/公顷土壤面积、优选为5g-5kg/公顷。
本发明活性化合物的制备和应用可见下述实施例。
制备实施例
实施例I-a-1
将5.6g(50mmol)叔丁醇钾加到30ml无水DMF中并在60℃下与10.6g存在于20ml DMF中的实施例II-8的混合物混合,在60℃搅拌3小时,将该反应液加到冰水中并用浓盐酸酸化,过滤沉淀、洗涤并干燥。
产量:7.4g(理论量的77%),熔点(Fp.)>220℃。
实施例I-a-2
将9.8g(44mmol)2,4,5-三甲基苯基-氯羰基烯酮加到80ml无水二甲苯中并在20℃、隔绝潮气的条件下滴加8.1g(44mmol)存在于30ml无水二甲苯中的三甲基甲硅烷基氧基亚甲基环己烷。加热回流8小时,然后滴加7.3ml甲醇并继续加热回流2小时,用水、饱和的盐水洗涤并用硫酸钠干燥,减压浓缩,所得残余物经硅胶(35-70μm)色谱纯化,用甲苯/丙酮(20∶1)洗脱。
产量:3.9g(
理论量的27%),Fp.174-175℃。
实施例I-a-3
将9.4g(42.2mmol)2,4,5-三甲基苯基-氯羰基烯酮加到80ml无水二甲苯中并在20℃、隔绝潮气的条件下滴加7.1g(42.2mmol)存在于30ml无水二甲苯中的三甲基甲硅烷基氧基亚甲基环戊烷。加热回流8小时,然后用水、饱和的盐水洗涤并用硫酸钠干燥有机相,浓缩,所得残余物经硅胶(35-70μm)色谱纯化,用甲苯/丙酮(20∶1)洗脱。
产量:3.2g(
理论量的25%),Fp.122-124℃。
类似于实施例I-a-1、I-a-2和I-a-3并按制备的一般说明得到下列式I-a的化合物:
实施例编号W | X | Y | Z | B | A | Q1 | Q2 | Fp.℃ |
I-a-4 HI-a-5 HI-a-6 HI-a-7 CH3I-a-8 HI-a-9 CH3I-a-10 CH3I-a-11 CH3 | CH3CH3CH3CH3CH3CH3CH3CH3 | 4-Cl5-(4-Cl-C6H4)5-(4-Cl-C6H4)4-CH35-CH33-CH33-CH34-CH3 | HHHHH4-CH34-CH3H | CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3 | OCH3HCH3CH3OCH3OCH3OHOCH3 | HHCH3CH3HHHH | 164-166蜡状物125140油状物121-122184-186115-117 |
实施例编号 | W | X | Y | Z | B | A | Q1 | Q2 | Fp.℃ |
I-a-25I-a-26I-a-27I-a-28I-a-29I-a-30I-a-31 | HHBrC2H5ClClH | CH3CF3C3H7C2H5ClClCl | 5-(2-Ch3,4-Cl-C6H3)4-Cl4-Br4-Br4-CF34-Cl5-(4-Cl-C6H4) | HHHHHHH | CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3 | 202-203℃185-186℃油状物178-180℃233-234℃>250℃204-205℃ |
实施例I-A-b-1
将1.5g(3.9mmol)实施例I-a-1的化合物加到15ml无水二氯甲烷中并与0.78ml(5.85mmol)三乙胺混合。在0℃下加入0.57g(5.07mmol)异丁酰氯并在室温下搅拌2小时。用10%的柠檬酸萃取反应液并用二氯甲烷洗涤。然后用1N NaOH萃取并再用二氨甲烷洗涤、干燥并蒸发溶剂。
产量:1.2g(
理论量的68%)。1H-NMR(400MHz,DMSO):δ=0.69(d,6H,(CH3)2-CH);1.17(s,6H,(CH3)2-C),1.52(s,6H,(CH3)2-C-O),2.1l(s,6H,2Ar-CH3)ppm。
类似于实施例(I-A-b-1)并按照制备的一般说明得到下列式(I-A-b)和(I-B-b)化合物:
式I-A-b和I-B-b的异构体混合物通过硅胶色谱分离。
实施例I-A-c-1
将1.5g(3.9mmol)实施例I-a-1的化合物加到15ml无水二氯甲烷中并与0.78ml(5.85mmol)三乙胺混合。在0℃下加入0.63g(5.07mmol)氯甲酸异丙酯并在室温下搅拌2小时。用10%的柠檬酸萃取反应液并用二氯甲烷洗涤。然后用1N NaOH萃取并再用二氯甲烷洗涤、干燥并蒸发溶剂。
1H-NMR(400MHz,DMSO):δ=1.08(d,6H,(CH3)2-CH);1.16(s,6H,(CH3)2-C),2.11(s,6H,2Ar-CH3),7.36(s,2H,2Ar-H)ppm。
类似于实施例I-A-c-1并按照制备的一般说明得到下列式(I-A-c)和(I-B-c)化合物:
实施例编号 | W | X | Y | Z | B | A | Q1 | Q2 | M | R2 | Fp.℃ |
I-A-c-10I-A-c-11I-A-c-12 | HHH | CH3CH3CH3 | 5-(4-Cl-C6H4)5-(3-Cl-C6H4)5-Br | 4-CH3HH | CH3CH3CH3 | CH3CH3CH3 | CH3CH3CH3 | CH3CH3CH3 | OOO | C2H5C2H5C2H5 | 油状物油状物 |
实施例II-1
酰氯的制备:
将9.0g(34.5mmol)2-甲基-5-(4-氯苯基)-苯基乙酸加到50ml含有2滴DMF的无水甲苯中并加入6.15g(51.8mmol;3.74ml)亚硫酰氯。在100℃下搅拌直至不再产生气体,蒸发除去溶剂。
将6.00g(34.5mmol)3-羟基-2,2,3-三甲基丁酸乙酯和10.3g(34.5mmol)酰氯在40ml无水甲苯中加热回流过夜。然后蒸发除去溶剂并将反应混合物通过硅胶柱色谱纯化(石油醚∶乙酸乙酯,3∶1→1∶1)。
产量:11.6g(
理论量的80.6%)。
1H-NMR(DMSO,400MHz):δ=1.06(s,6H,2CH3),1.12(t,3H,CO2CH2CH3),1.50(s,6H,2CH3),2.26(s,3H,Ar-CH3),3.66(s,2H,CH2),4.00(q,2H,CO2CH2CH3)ppm。
类似于实施例II-1并按照制备的一般说明得到下列式(II)化合物:
实施例编号 | W | X | Y | Z | B | A | Q1 | Q2 | R8 | Fp.℃ |
II-12II-13II-14II-15II-16II-17II-18II-19 | HHHBrC2H5ClClH | CH3CH3CF3C3H7C2H5ClClCl | 5-Br5-(3,5-Cl2-C6H3)4-Cl4-Br4-Br4-CF34-Cl5-(4-Cl-C6H4) | HHHHHHHH | CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3 | CH3CH3CH3CH3CH3CH3CH3CH3 | C2H5C2H5C2H5C2H5C2H5C2H5C2H5C2H5 | 油状物油状物油状物油状物油状物油状物油状物油状物 |
所得化合物为油状物并不经进一步纯化用于制备式(I-a)化合物。
应用实施例
实施例A
根结线虫属(Meloidogyne)-试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与上述量的溶剂和乳化剂混合,并用水将该浓缩物稀释至所需浓度。
给容器填充沙子、活性化合物的溶液、假根结线虫卵/幼虫悬浮液和莴苣种子。莴苣种子发芽,并且发育成植物。在根部形成了瘿。
所需时间后,根据形成的瘿作为度量标准来确定以%表示的杀线虫作用。100%表示没有发现任何瘿;0%表示在治疗的植物上的瘿数目相当于在未治疗的对照植物上的瘿数目。
例如下列制备实施例的化合物在该试验中显示有良好效果。
表A
对植物有害的线虫
根结线虫属-试验
活性化合物 | 活性化合物的浓度,ppm | 14天后的杀死率,% |
实施例I-a-5 | 20 | 100 |
实施例I-B-b-17 | 20 | 90 |
实施例I-B-c-1 | 20 | 90 |
实施例I-A-b-4 | 20 | 90 |
实施例I-B-c-2 | 20 | 100 |
实施例I-A-b-10 | 20 | 100 |
实施例I-A-b-1 | 20 | 100 |
实施例B
瘤额蚜属(Myzus)-试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
通过将被桃蚜虫(桃蚜)严重侵袭的甘蓝(Brassica oleracea)叶子浸入规定浓度的活性化合物制剂中进行处理。
在规定时间后确定用%表示的杀灭作用。其中100%表示所有蚜虫都被杀死;0%表示没有蚜虫被杀死。
例如下列制备实施例的化合物在该试验中显示有良好效果。
表B
对植物有害的昆虫
瘤额蚜属-试验
活性化合物 | 活性化合物的浓度,ppm | 6天后的杀死率,% |
实施例I-a-5 | 1000 | 95 |
实施例I-a-7 | 1000 | 90 |
实施例I-a-6 | 1000 | 95 |
实施例C
全爪螨属(Panonychus)-试验
溶剂:3重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
用希望浓度的活性化合物制剂对被果树红蜘蛛严重侵袭的约30cm高的小李子树进行喷雾。
在规定时间后确定用%表示的作用。其中100%表示所有红蜘蛛都被杀死;0%表示没有红蜘蛛被杀死。
例如下列制备实施例的化合物在该试验中显示有良好效果。
表C
对植物有害的螨
全爪螨属-试验
活性化合物 | 活性化合物的浓度,ppm | 14天后的杀死率,% |
实施例I-a-6 | 200 | 100 |
实施例D
Phaedon幼虫-试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝(Brassica oleracea)叶浸入希望浓度的活性化合物制剂中进行处理并在叶子仍潮湿时放上辣根猿叶虫(Phaedoncochleariae)的幼虫。
在规定时间后确定用%表示的杀灭作用。其中100%表示所有甲虫幼虫都被杀死;0%表示没有甲虫幼虫被杀死。
例如下列制备实施例的化合物在该试验中显示有良好效果。
表D
对植物有害的昆虫
Phaedon幼虫-试验
活性化合物 | 活性化合物的浓度,ppm | 7天后的杀死率,% |
实施例I-a-5 | 1000 | 100 |
实施例I-a-6 | 1000 | 100 |
实施例I-A-b-10 | 1000 | 100 |
实施例I-A-c-3 | 1000 | 90 |
实施例I-a-13 | 1000 | 100 |
实施例I-a-1 | 1000 | 100 |
实施例I-A-b-11 | 1000 | 100 |
实施例E
草地贪夜娥(Spodoptera frugiperda)-试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
将甘蓝(Brassica oleracea)叶浸入希望浓度的活性化合物制剂中进行处理并在叶子仍潮湿时放上草地贪夜娥的毛虫。
在规定时间后确定用%表示的杀灭作用。其中100%表示所有毛虫都被杀死;0%表示没有毛虫被杀死。
例如下列制备实施例的化合物在该试验中显示有良好效果。
表E
对植物有害所昆虫
草地贪夜娥-试验
活性化合物 | 活性化合物的浓度,ppm | 7天后的杀死率,% |
实施例I-a-6 | 1000 | 100 |
实施例I-A-b-10 | 1000 | 100 |
实施例F
红叶螨属试验(OP-抗性/浸泡处理)
溶剂:30重量份的二甲基甲酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与上述量的溶剂和乳化剂混合,并用水将该浓缩物稀释至所需浓度。
通过浸泡在所需浓度的活性化合物制剂中来处理被所有阶段的温室红叶螨(二点叶螨)严重感染的大豆植物(菜豆)。
所需时间后,确定以%表示的作用。100%表示所有红叶螨都被杀死;0%表示没有一个叶螨被杀死。
例如下列制备实施例的化合物在该试验中显示有良好效果。
表F
对植物有害的螨
红叶螨属试验(OP-抗性/浸泡处理)
活性化合物 | 活性化合物的浓度,ppm | 7天后的杀死率,% |
实施例I-a-6 | 100 | 100 |
实施例I-B-b-17 | 100 | 100 |
实施例I-B-c-1 | 100 | 100 |
实施例I-B-c-2 | 100 | 99 |
实施例I-B-b-16 | 100 | 100 |
实施例I-A-c-3 | 0.01 | 100 |
实施例G
根结线虫属-试验
溶剂:8重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与上述量的溶剂和乳化剂混合,并用水将该浓缩物稀释至所需浓度。
给容器填充沙子、活性化合物的溶液、假根结线虫卵/幼虫悬浮液和莴苣种子。莴苣种子发芽,并且发育成植物。在根部形成了瘿。
所需时间后,根据形成的瘿作为度量标准来确定以%表示的杀线虫作用。100%表示没有发现任何瘿;0%表示在治疗的植物上的瘿数目相当于在未治疗的对照植物上的瘿数目。
活性化合物、施用量和结果列入下表中:
表G
杀线虫剂
假根结线虫
活性化合物 | 在活性化合物的浓度,ppm时的杀死率 |
实施例I-a-7 | 20ppm=100% |
实施例H
单丝壳属(Sphaerotheca)-试验(黄瓜)/保护
溶剂:48.8重量份N,N-二甲基甲酰胺
乳化剂:1.2重量份烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与上述量的溶剂和乳化剂混合,并用水将该浓缩物稀释至所需浓度。
为了测试保护作用,按所述量用活性化合物制剂喷洒幼小黄瓜苗。处理后-天用单丝壳属fuliginea的孢子悬浮液给植物接种,然后将植物放入在70%相对湿度和23℃的温室中。
接种7天后进行评价。对此100%表示没有观察到侵害,0%表示作用程度与对照植物相当。
表H
单丝壳属-试验(黄瓜)/保护
活性化合物 | 活性化合物的用量,克/公顷 | 作用程度,% |
实施例I-B-b-13 | 750 | 70 |
实施例I-A-b-3 | 750 | 80 |
实施例I
临界浓度试验/土壤昆虫-处理转基因植物
测试昆虫:在土壤中的黄瓜条叶甲-幼虫
溶剂:7重量份的丙酮
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与上述量的溶剂混合,加入上述量的乳化剂,并用水将该浓缩物稀释至所需浓度。
将该活性化合物制剂浇灌到土壤上。活性化合物在制剂中的浓度实际上是无关的,起决定作用的只是以ppm(mg/l)表示的每单位体积土壤中活性化合物的重量。将土壤填充到0.25升盆中,并在20℃放置。
制备后立即向每个盆中放置5株预发芽的玉米作物,所述玉米作物是YIELD GUARD(Monsanto Comp.,USA的商标)品种。2天后,将测试昆虫放置到处理过的土壤内。再过7天后,通过计数露出土表的玉米作物来确定活性化合物的效力(1株作物=20%效力)。
实施例J
烟芽夜蛾试验-处理转基因植物
溶剂:7重量份的丙酮
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物与上述量的溶剂和上述量的乳化剂混合,并用水将该浓缩物稀释至所需浓度。
通过浸泡在所需浓度的活性化合物制剂中来处理Roundup Ready(Monsanto Comp.USA的商标)品种的大豆嫩枝(Glycine max),并在叶子仍然潮湿时让烟草芽虫烟芽夜蛾在其上面定殖。
所需时间后,确定对昆虫的杀死率。
Claims (15)
1.式(I)化合物
其中
W表示氢、C1-C6-烷基、氟、氯、溴或C1-C6-烷氧基,
X表示氟、氯、溴、C1-C6-烷基、C1-C4-卤代烷基、C1-C6-烷氧基、C1-C4-卤代烷氧基、各自任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基取代的苯基或各自任选被C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基取代的苄基氧基,
Y表示氢、C1-C6-烷基、C1-C4-卤代烷基、氟、氯、溴或表示
V1表示氢、卤素、C1-C12-烷基或C1-C4-卤代烷基,
V2表示氢、氟、氯、C1-C6-烷基、或C1-C4-卤代烷氧基,
V3表示氢、氟、氯、甲基或甲氧基,
Z表示氢、氟、氯、溴、C1-C6-烷基或C1-C4-卤代烷基,第一个条件是如果Y表示被V1、V2和V3取代的苯基,则W、X和Z不表示溴,
A表示氢或各自任选被卤素取代的C1-C12-烷基,
B表示氢或C1-C6-烷基,或
A、B和与其连接的碳原子表示饱和的C3-C10-环烷基或不饱和的C5-C10-环烷基,其中任选一个环单元被氧或硫代替和其任选被C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-烷基硫基、
卤素或苯基一或二取代,条件是Q1和Q2不另外形成环,或B和Q1一起表示任选被C1-C4-烷基相同或不同地一或二取代的C3-C6-链烷二基,其中两个不相邻的碳原子任选形成另一3-6-元环,或Q1表示氢、羟基、C1-C6-烷基、C1-C6-烷氧基或C1-C6-烷基酰基氧基,
Q2表示氢或C1-C4-烷基,
其中
L表示氧或硫,和
M表示氧或硫,
R1表示任选被卤素取代的C1-C20-烷基或者被卤素取代的苯基或吡啶基,
R2表示任选被卤素取代的C1-C20-烷基。
2.按照权利要求1的式(I)化合物、其中,
W表示氢、C1-C4-烷基、氯或溴,
X表示氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基或C1-C2-卤代烷氧基,
Y表示氢、C1-C4-烷基、C1-C2-卤代烷氧基、氟、氯、溴或表示基团
V1表示氢、氟、氯、溴、C1-C6-烷基或C1-C2-卤代烷基,
V2表示氢、氟、氯或C1-C4-烷基,
Z表示氢、氟、氯、溴、C1-C4-烷基或C1-C2-卤代烷基,
第一个条件是如果Y表示被V1、V2和V3取代的苯基,则W、X和Z不表示溴,
A表示氢或各自任选被氟取代的C1-C8-烷基,
B表示氢或C1-C4-烷基,或
A、B和与其连接的碳原子表示饱和的C5-C7-环烷基,其中任选一个环单元被氧代替和其任选被C1-C4-烷基、三氟甲基或C1-C4-烷氧基一取代,条件是Q1和Q2不形成另外的环,或
B和Q1一起表示任选被C1-C2-烷基一取代的C3-C4-链烷二基,其中两个不直接相邻的碳原子任选形成另一个五-六元环,或
Q1表示氢、羟基、C1-C4-烷基、C1-C4-烷氧基或C1-C4-烷基酰基氧基,
Q2表示氢、甲基或乙基,或
其中
L表示氧或硫,和
M表示氧或硫,
R1表示任选被氟或氯取代的C1-C16-烷基,或
表示任选被氟、氯或溴一或二取代的苯基,或
表示各自任选被氟、氯或溴一取代的吡啶基,
R2表示任选被氟一至三取代的C1-C16-烷基。
3.按照权利要求1的式(I)化合物,其中
W表示氢、氯、溴、甲基或乙基,
X表示氯、溴、甲基、乙基、正丙基、甲氧基、乙氧基、三氟甲基、二氟甲氧基或三氟甲氧基,
Y表示氢、甲基、乙基、丙基、异丙基、氟、氯、溴或基团
V1表示氢、氟、氯、溴、甲基、乙基、异丙基、叔丁基或三氟甲基,
V2表示氢、氟、氯或甲基,
Z表示氢、氟、氯、溴、甲基或三氟甲基,条件是如果Y表示被V1和
V2取代的苯基,则W、X和Z不表示溴,
A表示氢、甲基、乙基、正丙基、异丙基、正丁基或异丁基,
B表示氢、甲基或乙基,或
A、B与和其连接的碳原子表示饱和的C5-C6-环烷基,其中任选一个环单元被氧代替和其任选被甲基、乙基、甲氧基或乙氧基一取代,条件是Q1和Q2不形成另外的环,或
B和Q1一起表示任选被甲基一取代的C3-C4-链烷二基,其中两个不直接相邻的碳原子任选形成另一个三-六元环,或
Q1表示氢、羟基、甲基、乙基、正丙基、异丙基、甲氧基、乙氧基、丙氧基、乙酰基氧基或丙酰基氧基,
Q2表示氢、甲基或乙基,或
其中
L表示氧或硫,和
M表示氧或硫,
R1表示任选被氟或氯取代的C1-C8-烷基或
被氟、氯或溴一取代的苯基,或
表示各自任选被氯或溴一取代的吡啶基,
R2表示C1-C8-烷基。
4.按照权利要求1的式(I)化合物,其中
W表示氢、甲基、乙基、氯或溴,
X表示甲基、乙基、正丙基、三氟甲基或氯,
Y表示甲基、三氟甲基、氯、溴,表示任选被氯和/或甲基一或二取代的苯基,
Z表示氢或甲基,条件是如果Y表示取代的苯基,则W不表示溴,
A表示甲基或乙基,
B表示甲基或乙基,或
A、B与和其连接的碳原子表示环丙基或环己基,或
B和Q1一起表示任选被甲基一取代的C4-链烷二基,
Q1表示氢、甲基、甲氧基、乙氧基、丙氧基、羟基或乙酰基氧基,
Q2表示氢或甲基,
G表示氢(a)或下列基团之一
其中
R1表示C1-C4-烷基,或表示各自被氯一取代的苯基或吡啶基,
R2表示C1-C4-烷基。
5.制备按照权利要求1的式(I)化合物的方法,其特征在于为了得到
(A)式(I-a)化合物
其中
A、B、Q1、Q2、W、X、Y和Z具有权利要求1所述的含义,
使式(II)化合物
其中
A、B、Q1、Q2、W、X、Y和Z具有权利要求1所述的含义,
和
R8表示C1-C6-烷基,
在稀释剂存在下和在碱存在下进行分子内缩合;
(B)为了得到式(I-a)至(I-c)化合物
其中A、B、G、Q1、Q2、W、X、Y和Z具有权利要求1所述的含义,
使式(I-a′)至(I-c′)化合物,
其中
A、B、R1、R2、L、M、Q1、Q2具有权利要求1所述的含义,W′、X′、Y′和Z′分别具有权利要求1所述的W、X、Y和Z的含义并且其中至少基团W′、X′、Y′之一表示氯、溴或碘,
和Z′不表示溴或碘,
α)先与式(III)化合物
其中
R9表示氢,和
R10表示C1-C4-烷基或苯基,
在溶剂、碱和催化剂存在下反应并随后除去甲硅烷基,
或
β)与式(IV)化合物
其中
R9表示氢、甲基或乙基,和
R10表示C1-C4-烷基,
在溶剂,任选在碱和在催化剂存在下反应,
或
γ)在特殊情况下,如果Y′表示氯、溴或碘和W′、X′和Z′不表示溴或碘,与式(V)的硼酸
其中
Y表示任选取代的苯基,
在溶剂、碱和催化剂存在下反应;
(C)为了得到上述式(I-b)化合物,其中A、B、Q1、Q2、R1、W、X、Y和Z具有权利要求1所述的含义,
使上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有权利要求1所述的含义,分别
(α)与式(VI)化合物
其中
R1具有权利要求1所述的含义,和
Hal表示卤素
或
(β)与式(VII)化合物
R1-CO-O-CO-R1 (VII)
其中
R1具有权利要求1所述的含义,
任选在稀释剂存在下和任选在酸结合剂存在下反应;
(D)为了得到上述式(I-c)化合物,其中A、B、Q1、Q2、R2、M、W、X、Y和Z具有权利要求1所述的含义和L表示氧,
使上述(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有权利要求1所述的含义,分别
与式(VIII)化合物
R2-M-CO-Cl (VIII)
其中
R2和M具有权利要求1所述的含义,
任选在稀释剂存在下和任选在酸结合剂存在下反应;
(E)为了得到上述(I-c)化合物,其中A、B、Q1、Q2、R2、M、W、X、Y和Z具有权利要求1所述的含义和L表示硫,
使上述式(I-a)化合物,其中A、B、Q1、Q2、W、X、Y和Z具有权利要求1所述的含义,分别
与式(IX)化合物
其中
M和R2具有权利要求1所述的含义,
任选在稀释剂存在下和任选在酸结合剂存在下反应,
以及
F)式(XVI)化合物
其中
A和B具有权利要求1所述的含义,和
Alk表示具有1-4个碳原子的烷基,
分别与式(XVII)化合物
其中
W、X、Y和Z具有权利要求1所述的含义,和
Hal表示氯或溴,
任选在稀释剂或稀释剂混合物存在下并任选在酸结合剂存在下反应。
7.农药,其特征在于含有至少一种按照权利要求1的式(I)化合物。
8.除草剂,其特征在于含有至少一种按照权利要求1的式(I)化合物。
9.控制动物害虫的方法,其特征在于,将按照权利要求1的式(I)化合物作用于害虫和/或其栖息地。
10.控制不希望的植物的方法,其特征在于,将按照权利要求1的式(I)化合物用于土壤和地面上的植物部分。
11.按照权利要求1的式(I)化合物用于控制动物害虫和不希望的植物的用途。
12.制备农药的方法,其特征在于将按照权利要求1的式(I)化合物与增量剂和/或表面活性剂混合。
13.制备除草剂的方法,其特征在于将按照权利要求1的式(I)化合物与增量剂和/或表面活性剂混合。
14.按照权利要求1式(I)化合物用于制备农药的用途。
15.按照权利要求1式(I)化合物用于制备除草剂的用途。
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EP (1) | EP1303505B1 (zh) |
JP (1) | JP4898070B2 (zh) |
KR (1) | KR100798733B1 (zh) |
CN (1) | CN1229368C (zh) |
AT (1) | ATE407128T1 (zh) |
AU (3) | AU7056001A (zh) |
BR (1) | BR0112063B1 (zh) |
CA (1) | CA2412152C (zh) |
DE (2) | DE10030094A1 (zh) |
ES (1) | ES2312453T3 (zh) |
MX (1) | MXPA02012604A (zh) |
PL (1) | PL359216A1 (zh) |
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DE10311300A1 (de) * | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
DE10337497A1 (de) | 2003-08-14 | 2005-03-10 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-Pyrazolidin-3,5-dion-Derivate |
CN1310899C (zh) | 2003-11-11 | 2007-04-18 | 沈阳化工研究院 | 具有杀虫、杀菌活性的苯并吡喃酮类化合物及制备与应用 |
DE102004032421A1 (de) * | 2004-07-05 | 2006-01-26 | Bayer Cropscience Ag | Phenylsubstituierte [1.2]-Oxazin-3,5-dion-und Dihydropyron-Derivate |
DE102004035133A1 (de) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern |
DE102005059469A1 (de) * | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
US8680012B2 (en) * | 2006-12-14 | 2014-03-25 | Syngenta Crop Protection Llc | 4-phenyl-pyrane-3,5-diones,4-phenyl-thiopyrane-3,6-diones and cyclohexanetriones as novel herbicides |
GB0704652D0 (en) * | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
US7901701B2 (en) * | 2007-10-29 | 2011-03-08 | Lignotech Usa, Inc. | Methods for producing dried pesticide compositions |
NZ585790A (en) * | 2007-12-13 | 2012-02-24 | Syngenta Ltd | 4-Phenylpyrane-3,5-diones, 4-phenylthiopyrane-3,5-diones and 2-phenylcyclohexane-1,3,5-triones as herbicides |
WO2009150095A1 (en) * | 2008-06-12 | 2009-12-17 | Syngenta Participations Ag | Pesticidal compositions containing a pyrandione or a thiopyrandione or a cyclohexanetrione derivative |
GB0810815D0 (en) * | 2008-06-12 | 2008-07-23 | Syngenta Ltd | Novel herbicides |
GB0900864D0 (en) | 2009-01-19 | 2009-03-04 | Syngenta Ltd | Novel Herbicides |
EA024266B1 (ru) | 2009-03-11 | 2016-09-30 | Байер Интеллектуэль Проперти Гмбх | Кетоенолы, замещенные галоидалкилметиленоксифенилом, и их применение |
US20100278890A1 (en) * | 2009-04-29 | 2010-11-04 | Lignotech Usa, Inc. | Use of Lignosulfonates in Suspo-emulsions for Producing Pesticide Compositions |
EP2454224A1 (en) | 2009-07-17 | 2012-05-23 | Syngenta Limited | Novel herbicides |
DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
CA2855948C (en) | 2011-08-11 | 2020-07-28 | Bayer Cropscience Ag | 1,2,4-triazolyl-substituted keto-enols |
DK2806741T3 (da) | 2012-01-26 | 2020-05-18 | Bayer Ip Gmbh | Phenylsubstituerede ketoenoler til bekæmpelse af fiskeparasitter |
EP2925736B1 (en) * | 2012-11-28 | 2017-01-04 | Sumitomo Chemical Co., Ltd | Dihydropyrone compounds and herbicides comprising the same |
CN104430351A (zh) * | 2014-12-31 | 2015-03-25 | 江阴苏利化学股份有限公司 | 一种含有吡喃酮的防治甘蓝蚜虫的农药组合物 |
CN108164072A (zh) * | 2018-01-15 | 2018-06-15 | 昆明理工大学 | 一种微波-超重力联合处理稀土生产氨氮废水的装置和应用方法 |
CN112850985B (zh) * | 2021-01-11 | 2023-05-26 | 广东腾昊建设工程有限公司 | 一种用于水处理的微滤净化处理设备 |
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US3542809A (en) | 1968-10-23 | 1970-11-24 | Pfizer | Synthesis of arylchlorocarbonyl ketenes |
FR2368952A1 (fr) * | 1976-02-25 | 1978-05-26 | Lipha | Nouveaux aminoalcoxy-4 (2 h) pyranone-2,3 substitues-5,6 condenses |
JPH0625210A (ja) * | 1991-05-10 | 1994-02-01 | Dainippon Ink & Chem Inc | 光学活性5,6−ジヒドロ−2−ピロン誘導体、及びその製造方法、その誘導体を含む液晶組成物及び液晶表示素子 |
EP0702670A1 (de) | 1993-06-07 | 1996-03-27 | Bayer Ag | Iodpropargylcarbamate und ihre verwendung als biozide im pflanzen- und materialschutz |
US5840751A (en) | 1993-11-19 | 1998-11-24 | Warner-Lambert Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
AU680064B2 (en) | 1993-11-19 | 1997-07-17 | Parke, Davis & Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
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US5994274A (en) | 1995-06-30 | 1999-11-30 | Bayer Aktiengesellschaft | Dialkyl phenyl halide-substituted keto-enols for use as herbicides and pesticides |
DE19708607A1 (de) * | 1997-03-03 | 1998-09-10 | Bayer Ag | 2-Arylcyclopentan-1,3-dione |
DE19808261A1 (de) | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
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AU2001270560C1 (en) | 2002-01-02 |
US20040102516A1 (en) | 2004-05-27 |
CN1443181A (zh) | 2003-09-17 |
JP2004501144A (ja) | 2004-01-15 |
DE50114285D1 (de) | 2008-10-16 |
RU2003101389A (ru) | 2004-06-27 |
UA74835C2 (en) | 2006-02-15 |
MXPA02012604A (es) | 2004-05-17 |
BR0112063A (pt) | 2003-05-13 |
JP4898070B2 (ja) | 2012-03-14 |
EP1303505B1 (de) | 2008-09-03 |
AU7056001A (en) | 2002-01-02 |
EP1303505A1 (de) | 2003-04-23 |
BR0112063B1 (pt) | 2012-01-10 |
US6906007B2 (en) | 2005-06-14 |
DE10030094A1 (de) | 2001-12-20 |
CA2412152A1 (en) | 2001-12-27 |
WO2001098288A1 (de) | 2001-12-27 |
AU2006228042A1 (en) | 2006-11-09 |
CA2412152C (en) | 2007-08-28 |
ES2312453T3 (es) | 2009-03-01 |
KR20030031494A (ko) | 2003-04-21 |
ATE407128T1 (de) | 2008-09-15 |
KR100798733B1 (ko) | 2008-01-29 |
PL359216A1 (en) | 2004-08-23 |
AU2001270560B2 (en) | 2006-03-09 |
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