CN1329611A - 具有杀虫作用的苯基乙酸杂环基酰胺 - Google Patents
具有杀虫作用的苯基乙酸杂环基酰胺 Download PDFInfo
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- CN1329611A CN1329611A CN99814170A CN99814170A CN1329611A CN 1329611 A CN1329611 A CN 1329611A CN 99814170 A CN99814170 A CN 99814170A CN 99814170 A CN99814170 A CN 99814170A CN 1329611 A CN1329611 A CN 1329611A
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- -1 Phenylacetic acid heterocyclyl amides Chemical class 0.000 title claims abstract description 111
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229960003424 phenylacetic acid Drugs 0.000 title claims abstract description 21
- 239000003279 phenylacetic acid Substances 0.000 title claims abstract description 21
- 230000000749 insecticidal effect Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 66
- 244000005700 microbiome Species 0.000 claims abstract description 13
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 12
- 241001465754 Metazoa Species 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 150000001266 acyl halides Chemical class 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000006416 CBr Chemical group BrC* 0.000 claims description 6
- 125000006414 CCl Chemical group ClC* 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 71
- 150000001721 carbon Chemical group 0.000 description 38
- 239000011737 fluorine Substances 0.000 description 31
- 229910052731 fluorine Inorganic materials 0.000 description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 27
- 239000002585 base Substances 0.000 description 26
- 239000000463 material Substances 0.000 description 25
- 229910052760 oxygen Inorganic materials 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 239000001301 oxygen Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 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 17
- 239000003995 emulsifying agent Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000001246 bromo group Chemical group Br* 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
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- 125000004093 cyano group Chemical group *C#N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 150000003851 azoles Chemical class 0.000 description 13
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
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- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 8
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- 241001674048 Phthiraptera Species 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 7
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- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 7
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- 239000003999 initiator Substances 0.000 description 7
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
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- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
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- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 210000002700 urine Anatomy 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
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- 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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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
本发明涉及式(Ⅰ)的新的苯基乙酸杂环基酰胺,其中R1,R2,R3,R4,A,X和n具有说明书中的定义。本发明还涉及制备这些新的物质的方法并且涉及它们杀灭不期望的微生物和动物害虫的用途(杀虫剂)。本发明还涉及式(Ⅱ)的新的中间体产物及其多种制备方法。
Description
本发明涉及新的苯基乙酸杂环基酰胺、它们的制备方法和它们防治不期望的微生物和动物害虫的用途。
已知多种N-(5-异噻唑基)-酰胺或N-(5-噻唑基)-酰胺具有杀虫和杀真菌性能(参见WO97-18198,WO97-26251和WO95-31448)。这些物质的活性是好的,但是有时在低浓度下不令人满意。
因此,本发明提供下式新的苯基乙酸杂环基酰胺其中R1 代表烷基,卤代烷基,烷氧基烷基,烷硫基烷基,烷氧基,烷硫基或者代表任选被取代的环烷基,R2 代表氢,烷基羰基,烷氧羰基或者代表各自任选被取代的芳基羰基,芳基氧基羰基或芳烷基氧基羰基,R3 代表氢或烷基,R4 代表任选被取代的烷基,任选被取代的链烯基,任选被取代的炔烃基,任选被取代的芳基,任选被取代的芳烷基,任选被取代的芳烷基氧基或者代表任选被取代的芳烷基氧基烷基,或者两个成对的或连位的R4基团与它们连接的碳原子一起形成饱和的或不饱和的、任选被取代的、其中包含一个或两个杂原子的5-或6-元环,n 代表1-4的整数,X 代表氮原子或者代表下式基团CH,C-Cl,C-Br,C-C≡CH,C-CN或
和A代表一个直接的键或一个CH2基团。
此外,发现通过下面的方法可以制备式(I)的苯基乙酸杂环基酰胺:a)任选地在稀释剂的存在下和在脱水剂的存在下,使式(II)的氨基衍生物与式(III)的二元醇反应其中R1,R3和X如上定义,其中A,R4和n如上定义,以及b)任选地,在稀释剂的存在下和在酸结合剂的存在下将得到的下式的苯基乙酸杂环基酰胺与式(IV)的酰基卤反应其中R1,R3,R4,A,X和n如上定义,其中Hal代表氯或溴,和R5 代表烷基,烷氧基或者代表各自任选被取代的芳基,芳基氧基或芳烷基氧基。
最后,发现式(I)的苯基乙酸杂环基酰胺高度适合防治不期望的微生物和动物害虫。
出人意料地,本发明的化合物具有比结构最相近的作用方向相同的现有技术化合物好得多的杀真菌和杀昆虫活性。
式(I)提供了根据本发明的苯基乙酸杂环基酰胺的一般定义。
R1 优选代表C1-C4-烷基,具有1-5个氟、氯和/或溴原子的C1-C4-卤代烷基,代表C1-C4-烷氧基-C1-C4-烷基,C1-C4-烷硫基-C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基或者代表任选被相同或不同的选自C1-C4-烷基或卤素的取代基一-至三取代的C3-C6-环烷基。
R2 优选代表氢,C1-C4-烷基-羰基,C1-C4-烷氧基-羰基或者代表苯基羰基,苯基氧基-羰基或苯基-C1-C4-烷氧基-羰基,其中后提到的三个基团在苯基部分可以被相同或不同的选自下面的取代基一-至三取代:卤素,硝基,氰基,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷基,具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷氧基和/或具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷硫基。
R3 优选代表氢或C1-C4-烷基。
R4 优选代表C1-C12-烷基,具有1-8个相同或不同的卤原子的C1-C8-卤代烷基,C1-C4-羟基烷基,具有1-8个相同或不同的卤原子的C2-C8-卤代链烯基,C2-C8-炔烃基,具有1-8个卤原子的C2-C8-卤代炔烃基,C1-C8-烷氧基-C1-C4-烷基,C2-C8-链烯基氧基-C1-C4-烷基,C2-C8-炔烃基氧基-C1-C4-烷基,具有1-8个相同或不同的卤原子的C1-C8-卤代烷氧基-C1-C4-烷基,具有1-8个相同或不同的卤原子的C2-C8-卤代链烯基氧基-C1-C4-烷基,具有1-8个相同或不同的卤原子的C2-C8-卤代炔烃基氧基-C1-C4-烷基,C1-C8-烷氧羰基-C1-C4-烷基,C1-C8-烷基羰基氧基-C1-C4-烷基,具有1-8个相同或不同的卤原子的C1-C8-卤代烷基羰基氧基-C1-C4-烷基,C1-C8-烷硫基-C1-C4-烷基,或者代表苯基,烷基部分具有1-4个碳原子的苯基烷基,烷氧基部分具有1-4个碳原子的苯基烷氧基,或者代表烷基部分具有1-4个碳原子且氧基烷基部分具有1-4个碳原子的苯基烷氧基烷基,其中后提到的4个基团在苯基部分可以被相同或不同的选自下面的取代基一-至三取代:卤素,硝基,氰基,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷基,具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷氧基,具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷硫基,具有1-4个碳原子的烷基亚磺酰基,具有1-4个碳原子的烷基磺酰基,烷基部分具有1-4个碳原子的烷基羰基和烷氧基部分具有1-4个碳原子的烷氧基羰基。
此外,两个成对的或连位的R4基团与它们连接的碳原子一起优选代表饱和的或不饱和的5-或6-元环,其可以包含一个或两个氧、硫和/或氮原子,并且可以被卤素,具有1-4个碳原子的烷基和/或有1-4个碳原子的烷氧基一-或二取代。n 优选代表1,2或3,X 优选代表氮原子或者代表下式基团
CH,CCl,CBr,C-CN,C-C≡CH或
A 优选代表一个直接的键或一个CH2基团。R1 特别优选代表甲基,乙基,丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,具有1或2个碳原子和1-3个氟,氯和/或溴原子的卤代烷基,烷氧基部分具有1或2个碳原子并且烷基部分具有1或2个碳原子的烷氧基烷基,烷硫基部分具有1或2个碳原子并且烷基部分具有1或2个碳原子的烷硫基烷基,甲氧基,乙氧基,甲硫基,乙硫基,或者代表任选地被甲基,乙基,氟和/或氯一-或二取代的环戊基、环己基或环丙基。
R2 特别优选代表氢,甲基羰基,乙基羰基,甲氧羰基,乙氧羰基,丙氧羰基,异丙氧羰基,丁氧羰基,异丁氧羰基,仲丁氧羰基,叔丁氧羰基,苯基羰基,苯基氧基羰基或烷氧基部分具有1或2个碳原子的苯基烷氧基羰基,其中后提到的三个基团在苯基部分可以被相同或不同的选自下面的取代基一-或二取代:氟,氯,溴,硝基,氰基,甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,氯甲基,二氯甲基,二氟甲基,三氟甲基,三氟甲氧基和三氟甲硫基。
R3 特别优选代表氢,甲基或乙基。
R4 特别优选代表C1-C10-烷基,具有1-8个碳原子和1-8个氟,氯和/或溴原子的卤代烷基,具有1或2个碳原子的羟基烷基,C2-C8-链烯基,具有1-8个氟,氯和/或溴原子的C2-C8-卤代链烯基,C2-C8-炔烃基,具有1-8个氟,氯和/或溴原子的C2-C8-卤代炔烃基,C1-C8-烷氧基-C1-C2-烷基,C2-C8-链烯基氧基-C1-C2-烷基,C2-C8-炔烃基氧基-C1-C2-烷基,具有1-5个氟,氯和/或溴原子的C1-C6-卤代烷氧基-C1-C2-烷基,具有1-5个氟,氯和/或溴原子的C2-C6-卤代链烯基氧基-C1-C2-烷基,具有1-5个氟,氯和/或溴原子的C2-C6-卤代炔烃基氧基-C1-C2-烷基,C1-C8-烷氧羰基-C1-C2-烷基,C1-C8-烷基羰基氧基-C1-C2-烷基,具有1-5个氟,氯和/或溴原子的C1-C6-卤代烷基羰基氧基-C1-C2-烷基,C1-C6-烷硫基-C1-C2-烷基,或者代表苯基,烷基部分具有1或2个碳原子的苯基烷基,烷氧基部分具有1或2个碳原子的苯基烷氧基,或者代表烷基部分具有1或2个碳原子且氧基烷基部分具有1或2个碳原子的苯基烷氧基烷基,其中后提到的4个基团在苯基部分可以被相同或不同的选自下面的取代基一-至三取代:氟,氯,溴,硝基,氰基,甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,氯甲基,二氯甲基,二氟甲基,三氟甲基,三氟甲氧基,三氟甲硫基,甲基亚磺酰基,甲基磺酰基,甲基羰基,乙基羰基,甲氧羰基和/或乙氧羰基。
此外,两个成对的或连位的R4基团与它们连接的碳原子一起特别优选代表饱和的或一不饱和的6-元环,其可以包含一个或两个氧,硫和/或氮原子,并且可以被氟,氯,甲基,乙基和/或甲氧基一-或二取代。n 特别优选代表1或2。X 特别优选代表氮原子或者代表下式基团
CH,CCl,CBr,C-CN,C-C≡CH或
A 特别优选代表一个直接的键或代表一个CH2基团。R1 非常特别优选代表甲基,乙基,氯甲基,二氟甲基,三氟甲基,甲氧基甲基,乙氧基甲基,甲硫基甲基,甲氧基,乙氧基,甲硫基,环丙基,环戊基或环己基。R2 非常特别优选代表氢,甲基羰基,乙基羰基,甲氧羰基,乙氧羰基,苯基羰基,苯基氧基羰基或苯基甲氧基羰基,其中后提到的三个基团在苯基部分可以被相同或不同的选自下面的取代基一-或二取代:氟,氯,溴,硝基,氰基,甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,氯甲基,二氯甲基,二氟甲基,三氟甲基,三氟甲氧基和三氟甲硫基。R3 非常特别优选代表氢或甲基。R4 非常特别优选代表C1-C10-烷基,具有1-4个碳原子和1-5个氟,氯和/或溴原子的卤代烷基,羟基甲基,羟基乙基,C2-C6-链烯基,具有1-5个氟,氯和/或溴原子的C2-C6-卤代链烯基,C2-C6-炔烃基,具有1-5个氟,氯和/或溴原子的C2-C6-卤代炔烃基,C1-C6-烷氧基-甲基,C2-C6-链烯基氧基-甲基,C2-C6-炔烃基氧基-甲基,具有1-3个氟,氯和/或溴原子的C1-C4-卤代烷氧基-甲基,具有1-3个氟,氯和/或溴原子的C2-C4-卤代链烯基氧基-甲基,具有1-3个氟,氯和/或溴原子的C2-C4-卤代炔烃基氧基-甲基,C1-C4-烷氧羰基-甲基,C1-C4-烷基羰基氧基-甲基,具有1-3个氟,氯和/或溴原子的C1-C4-卤代烷基羰基氧基-甲基,C1-C4-烷硫基-甲基,或者代表苯基,烷基部分具有1或2个碳原子的苯基烷基,烷氧基部分具有1或2个碳原子的苯基烷氧基,或者代表苯基甲基氧基甲基,其中后提到的4个基团在苯基部分可以被相同或不同的选自下面的取代基一-或二取代:氟,氯,溴,硝基,氰基,甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,氯甲基,二氯甲基,二氟甲基,三氟甲基,三氟甲氧基,三氟甲硫基,甲基亚磺酰基,甲基磺酰基,甲基羰基,乙基羰基,甲氧羰基和乙氧羰基。
此外,两个成对的或连位的R4基团与它们连接的碳原子一起非常特别优选代表饱和的或一不饱和的6-元环,其可以包含一个或两个不邻接的氧原子,并且可以被氟,氯,甲基,乙基和/或甲氧基一-或二取代。n 非常特别优选代表1或2。X 非常特别优选代表氮原子或者代表下式基团
CH,CCl,CBr,C-CN,C-C≡CH或
A非常特别优选代表一个直接的键或代表一个CH2基团。
上述基团定义可以根据需要相互组合,个别定义也可能不用。
可以提到的根据本发明的式(I)的苯基乙酸杂环基酰胺是下面表中列出的化合物。表1 表1(续)表1(续)在该表中:Me=甲基Et=乙基Pr=丙基Bu=丁基Pent=戊基Hex=己基Hept=庚基Ph=苯基
表2其中下面结构单元具有表1中给出的定义。表3其中下面结构单元具有表1中给出的定义。表4其中下面结构单元具有表1中给出的定义。表5其中下面结构单元具有表1中给出的定义。表6其中下面结构单元具有表1中给出的定义。表7其中下面结构单元具有表1中给出的定义。表8其中下面结构单元具有表1中给出的定义。表9其中下面结构单元具有表1中给出的定义。表10其中下面结构单元具有表1中给出的定义。表11其中下面结构单元具有表1中给出的定义。表12其中下面结构单元具有表1中给出的定义。
式(II)提供了需要用作进行根据本发明的方法(a)的起始物的氨基衍生物的一般定义。在该结构式中,R1、R3和X优选具有与描述根据本发明的式(I)的化合物相关已经提到的作为对于这些基团优选的那些定义。
式(II)的氨基衍生物迄今为止没有公开过。它们可以通过下述方法制备:c)使式(V)的杂环基-胺其中R1和X如上定义,进行下面的反应之一:α)任选地在酸结合剂的存在下和任选地在稀释剂的存在下与式(VI)的酰基卤反应其中R3如上定义,和Hal1代表氯或溴,或者β)在催化剂的存在下和在稀释剂的存在下,与式(VII)的苯基乙酸衍生物反应其中R3如上定义。
式(V)提供了需要用作进行方法(c)的起始物的杂环基胺的一般定义。在该结构式中,R1和X优选具有与描述根据本发明的式(I)的化合物相关已经提到的作为对于这些基团优选的那些定义。
式(V)的杂环基胺是已知的或者可以通过已知方法制备(参见DE-A4328425,DE-A2249162,WO93-19054,WO94-21617,杂环化学杂志(J.Het.Chem.)26,1575(1989),Gazz.Chim.Ital.107,1(1977),Chem.Ber.195,57和EP-AO455356)。
式(VI)提供了需要用作进行方法(c,变化方法α)的反应成分的酰基卤的一般定义。在该结构式中,R3优选具有与描述根据本发明的式(I)的化合物相关已经提到的作为对于该基团优选的那些定义。Hal1优选代表氯。
式(VI)的酰基卤是已知的或者可以通过已知方法制备(参见Monatsh.Chem.85,80(1954)和J.Chem.Soc.1956,404)。
式(VII)提供了需要用作进行方法(c,变化方法β)的反应组分的苯基乙酸衍生物的一般定义。在该结构式中,R3优选具有与描述根据本发明的式(I)的化合物相关已经提到的作为对于该基团优选的那些定义。
式(VII)的苯基乙酸衍生物同样是已知的或者可以通过已知方法制备(参见上面提到的公开物)。
用于进行方法(c,变化方法α)的合适的酸结合剂是所有常规无机或有机碱。优选使用碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇盐,乙酸盐,碳酸盐或碳酸氢盐,例如氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,乙酸钠,乙酸钾,乙酸钙,碳酸钠,碳酸钾,碳酸氢钾,还有氢氧化铵,乙酸铵或碳酸铵,或者叔胺类,例如三甲基胺,三乙基胺,三丁基胺,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,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
用于进行方法(c,变化方法α)的合适的稀释剂是所有惰性有机溶剂。优选使用脂肪烃,脂环烃或芳香烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤代烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚;腈类,例如乙腈,丙腈,正-或异丁腈或苄腈;酰胺类,例如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酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜;砜类,例如环丁砜。
进行方法(c,变化方法α)时,反应温度可以在较宽的范围内变化。一般情况下,在-10℃至+150℃之间的温度下进行该反应,优选在0℃至100℃之间的温度下进行。
方法(c,变化方法α),和方法(c,变化方法β)和方法(a)和(b)一样,一般在大气压下进行,但是也可以在加压或减压下进行。
进行方法(c,变化方法α)时,对于每摩尔式(V)的杂环基胺一般使用等摩尔量的酰基卤和等摩尔量或过量的酸结合剂。使用常规方法后处理。一般情况下,反应终止后浓缩反应混合物,留下的残余物与水和一种与水不混溶的有机溶剂混合,分离有机相,洗涤,干燥并浓缩。留下的产物可以通过常规方法去除可能存在的所有杂质。
用于进行方法(c,变化方法β)的合适的催化剂是适合活化式(VII)的苯基乙酸衍生物的羧基的所有常规反应促进剂。优选使用羰基二咪唑和二-环己基-碳化二亚胺。此外,该反应也可以在水结合剂的存在下进行。
用于进行方法(c,变化方法β)的合适的稀释剂是常规用于这样的反应的所有惰性有机溶剂。优选使用脂肪烃,脂环烃或芳香烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤代烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷。
进行方法(c,变化方法β)时,反应温度可以在较宽的范围内变化。一般情况下,在0℃至80℃之间的温度下进行该反应,优选在10℃至70℃之间的温度下进行。
进行方法(c,变化方法β)时,对于每摩尔式(V)的杂环基胺一般使用等摩尔量的式(VII)的苯基乙酸衍生物和等摩尔量的催化剂。但是也可以使用过量的一种或另一种成分。使用常规方法进行后处理。一般情况下,吸滤沉淀出的固体,减压下浓缩滤液并且层析留下的残余物。
式(III)提供了需要用作进行根据本发明的方法(a)的反应组分的二元醇的一般定义。在该结构式中,A,R4和n优选具有与描述根据本发明的式(I)的化合物相关已经提到的作为对于该基团或者对于该指数优选的那些定义。
式(III)的二元醇是已知的或者可以通过已知方法制备。
用于进行根据本发明的方法(a)的合适的稀释剂是常规用于这样的反应的所有惰性有机溶剂。优选使用芳香烃,例如苯,甲苯或二甲苯。
用于进行根据本发明的方法(a)的合适的脱水剂是能有效脱水的所有常规试剂。优选使用酸,例如硫酸或对甲苯磺酸,还有干燥剂。例如无水硅胶或分子筛,还有原甲酸酯。
进行根据本发明的方法(a)时,反应温度同样可以在较宽的范围内变化。一般情况下,在0℃至150℃之间的温度下进行该反应,优选在10℃至130℃之间的温度下进行。
进行根据本发明的方法(a)时,对于每摩尔式(II)的胺衍生物一般使用1-2摩尔,优选1-1.5摩尔的式(III)的二元醇和1-5摩尔的脱水剂。使用常规方法进行后处理。一般情况下,依次用水和碱水溶液洗涤反应混合物,然后减压浓缩,并且如果需要,通过常规方法从留下的残余物去除可能仍然存在的任何杂质。
需要用作进行根据本发明的方法(b)的起始物的式(Ia)的苯基乙酸杂环基-酰胺是可以通过方法(a)制备的根据本发明的化合物。
式(IV)提供了需要用作进行根据本发明的方法(b)的反应组分的酰基卤的一般定义。在该结构式中,R5 优选代表C1-C4-烷基,C1-C4-烷氧基,或者代表苯基,苯基氧基或苯基-C1-C4-烷氧基,其中后提到的三个基团在苯基部分可以被相同或不同的选自下面的取代基一-至三取代:卤素,硝基,氰基,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷基,具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷氧基和具有1或2个碳原子和1-5个相同或不同的卤原子的卤代烷硫基。
R5 特别优选代表甲基,乙基,甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,仲丁氧基,叔丁氧基,苯基,苯基氧基,或烷氧基部分具有1或2个碳原子的苯基烷氧基,其中后提到的三个基团在苯基部分可以被相同或不同的选自下面的取代基一-或二取代:氟,氯,溴,硝基,氰基,甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,氯甲基,二氯甲基,二氟甲基,三氟甲基,三氟甲氧基和三氟甲硫基。
R5 非常特别优选代表甲基,乙基,甲氧基,乙氧基,苯基,苯基氧基或苯基甲氧基,其中后提到的三个基团在苯基部分可以被相同或不同的选自下面的取代基一-或二取代:氟,氯,溴,硝基,氰基,甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,氯甲基,二氯甲基,二氟甲基,三氟甲基,三氟甲氧基和三氟甲硫基。
式(IV)的酰基卤是已知的或者可以通过已知的方法制备。
用于进行根据本发明的方法(b)的合适的酸结合剂是所有常规无机或有机碱。优选使用碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇盐,乙酸盐,碳酸盐或碳酸氢盐,例如氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,乙酸钠,乙酸钾,乙酸钙,碳酸钠,碳酸钾,碳酸氢钾,还有氢氧化铵,乙酸铵或碳酸铵,或者叔胺类,例如三甲基胺,三乙基胺,三丁基胺,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,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
用于进行根据本发明的方法(b)的合适的稀释剂是所有惰性有机溶剂。优选使用脂肪烃,脂环烃或芳香烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤代烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚;腈类,例如乙腈,丙腈,正-或异丁腈或苄腈;酰胺类,例如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酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜;砜类,例如环丁砜。
进行根据本发明的方法(b)时,反应温度可以在较宽的范围内变化。一般情况下,在-10℃至+150℃之间的温度下进行该反应,优选在0℃至100℃之间的温度下进行。
进行根据本发明的方法(b)时,对于每摩尔式(Ia)的苯基乙酸杂环基-酰胺一般使用1-2摩尔的式(IV)的酰基卤和等摩尔量或过量的酸结合剂。使用常规方法进行后处理。一般情况下,反应终止后浓缩反应混合物,留下的残余物与水和一种与水不混溶的有机溶剂混合,分离有机相,洗涤,干燥并浓缩,通过常规方法从留下的残余物去除可能存在的任何杂质。
根据本发明的活性物质可以用来在农作物保护和材料保护中防治不期望的微生物,例如真菌和细菌。
农作物保护中使用杀真菌剂来防治根肿菌。(Plasmodiophoromycetes),卵孢真菌(Oomycetes),壶菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌纲(Deutermycetes)。
农作物保护中使用杀细菌剂来防治假单孢菌科(Pseudomonadaceae),根瘤菌科(Rhizobiaceae),肠杆菌科(Enterobacteriaceae),棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)。
作为例子可以提到上述属名下的真菌病和细菌病的一些病原体,但是不受此限制:黄单孢菌属种类(Xanthomonas),例如田野稻黄单孢菌变种(Xanthomonas campestris pv.oryzae);假单孢菌属种类(Pseudomonas),例如丁香黄瓜角斑病假单孢菌变种(Pseudomonas syringae pv.lachrymans);欧文氏杆菌属种类(Erwinia),例如解淀粉欧文氏杆菌(Erwiniaamylovora);腐霉属种类(Pythium),例如终极腐霉(Pythium ultimum);疫霉属种类(Phytophthora),例如蔓延疫霉(Phytophthorainfestans);假霜霉属种类(Pseudoperonospora),例如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);单轴霉属种类(Plasmopara),例如葡萄生单轴霉(Plasmoparaviticola);盘梗霉属种类(Bremia),例如莴苣盘梗霉(Bremia lactucae);霜霉属种类(Peronospora),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronospora brassicae);白粉菌属种类(Erysiphe),例如禾白粉菌(Erysiphe graminis);单丝壳菌属种类(Sphaerotheca),例如苍耳单丝壳菌(Sphaerothecafuliginea);柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaeraleucotricha);黑星菌属种类(Venturia),例如苹果黑星菌(Venturia inaequalis);核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pyrenophora graminea)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));旋孢菌属种类(Cochliobolus),例如禾旋孢菌(Cochliobolussativus)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));单胞锈菌属种类(Uromyces),例如疣顶单胞锈菌(Uromycesappendiculatus);柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Puccinia recondita);核盘菌属种类(Sclerotinia),例如油菜核盘菌(SclerotiniaSclerotiorum);腥黑粉菌属种类(Tilletia),例如小麦网腥黑粉菌(Tilletiacaries);黑粉菌属种类(Ustilago),例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);薄膜革菌属种类(Pellicularia),例如佐佐木氏薄膜革菌(Pellicularia sasakii);Pyricularia种类,例如Pyricularia oryzae;镰孢属种类(Fusarium),例如大刀镰孢(Fusarium culmorum);葡萄孢属种类(Botrytis),例如灰色葡萄孢(Botrytis cinerea);壳针孢属种类(Septoria),例如颖枯壳针孢(Septoria nodorum);小球腔菌属种类(Leptosphaeria),例如颖枯小球腔菌(Leptosphaerianodorum);尾孢属种类(Cercospora),例如Cercospora canescens;链格孢属种类(Alternaria),例如甘蓝黑斑病链格孢(Alternariabrassicae);假尾孢属种类(Pseudocercosporella),例如Pseudocercosporellaherpotrichoides。
植物对在防治植物病害所需要的浓度时的活性化合物具有好的耐受性的事实允许处理植物的地上部分,植物繁殖根株和种子,和处理土壤。
根据本发明的活性化合物特另成功地用于防治影响谷物的病害,例如霉病,以及葡萄、水果和蔬菜种植中的病害,例如抗黑星菌属种类(Venturia),柄球菌属种类(Podosphaera)和单轴霉属种类(Plasmopara)。它们还具有好的体外抗卵菌(Oomycetes)作用。
在材料保护中,根据本发明的活性化合物可以被用来保护工业材料不受不期望微生物的感染和破坏。
本说明书中的工业材料理解为是指制备出来在工业中使用的无生命材料。例如,欲意受本发明活性化合物保护不受微生物改变或破坏的工业材料可以是粘合剂,胶料,纸张和纸板,纺织品,皮革,木材,涂料和塑料制品,冷却润滑剂和其它能被微生物感染或破坏的材料。要保护的材料的范围内也可以提到生产工厂的部分,例如冷却水循环,其可能受微生物繁殖的不利影响。本发明范围内可以提到的工业材料优选是粘合剂,胶料,纸张和纸板,皮革,木材,涂料,冷却润滑剂和导热液,特别优选木材。
可以提到下面属种的微生物作为例子:链格孢属(Alternaria),例如纤细链格孢(Alternaria tenuis),曲霉属(Aspergillus),例如黑色曲霉(Aspergillus niger),毛壳霉属(Chaetomium),例如球毛壳霉(Chaetomium globosum),粉孢革菌属(Coniophora),例如单纯粉孢革菌(Coniophora puetana),香菇属(Lentinus),例如虎皮香菇(Lentinus tigrinus),多孔菌属(Polyorus),例如变色多孔菌(Polyorus versicolor),短柄霉属(Aureobasidium),例如出芽短柄霉(Aureobasidiumpullulans),Sclerophoma,例如Sclerophoma pityophila,木霉属(Trichoderma),例如绿色木霉(Trichoderma viride),埃希氏杆菌属(Escherichia),例如大肠埃希氏杆菌(Escherichiacoli),假单孢菌属(Pseudomonas),例如铜绿假单孢菌(Pseudomonasaeruginosa),葡萄球菌属(Staphylococcus),例如金黄色葡萄球菌(Staphylococcusaureus)。
根据本发明的活性化合物还适合防治动物害虫,特别是农业,森林,园艺学,贮存产品保护和材料保护,以及卫生领域或兽药领域所遇到的昆虫,蛛形纲和线虫,并且具有好的植物耐受性并且对温血动物毒性低。本发明化合物在一般敏感性和抗性物和抗发育的所有或某些阶段方面是有效的。上述动物害虫包括:等足目(Isopoda),例如Oniseus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber;多足纲目(Diplopoda),例如Blaniulus gutttulatus;唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.);综合纲目(Symphyla),例如Scutigerella immaculata;缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina);弹尾目(Collembola),例如Onychiurus armatus;直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoriamigratorioides),长额负蝗(Melanoplus differentialis)和Schistocerca gregaria;革翅目(Dermaptera),例如欧洲球螋(Forficula aurieularia);等翅目(Isoptera),例如白蚁属(Reticulitermes spp.);虱目(Anoplura),例如头虱(Pediculus humanus corporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.);食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalineaspp.;缨翅目(Thysanoptera),例如温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci);异翅亚目(Heteroptera),例如褐盾蝽属(Eurygaster spp.),Dysdercusintermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimexlectularius),Rhodnius prolixus和吸血猎蝽属(Triatoma spp.);同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphisgossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Aphis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),葡萄根瘤蚜(Phylloxera vastatrix),青霉菌(Pemphigus spp.),Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodonhumuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelis bilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotus hederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.);鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletisblancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutellamaculipennis),天幕毛虫(Malacosoma neustria),Euproctischrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrixthurberiella),Phyllocnisti citrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Eariasinsulana),夜蛾属(Heliothis spp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestra brassicae),Panolis flammea,斜纹夜蛾(Prodenialitura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilospp.),Pyrausta nubilalis,Ephestia kuehniella,大黄螟(Galleriamellonella),袋衣蛾(Tineola bisselliella),网衣蛾(Tineapellionella),褐织叶蛾(Hofmannophilapseudospretella),Cacoeciapodana,Capua reticulana,云杉卷叶蛾(Choristoneurafumiferana),葡萄果蠹蛾(Clysia ambiguella),茶黄卷叶蛾(Homonamagnanima)和栎绿卷叶蛾(Tortrix viridana);鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,Bruehidius obtectus,大豆象(Acanthoscelides obtectus),家天牛(Hylotrupes bajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemlineata),Phaedoncochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodeschrysocephala),墨西哥豆瓢虫(Epilachna varivestis),Atomariaspp.,锯胸谷盗(Oryzaephilus surinamens),象甲属(Anthonomusspp.),米象属(Sitophilus spp.),Otiorrhynchus sul catus,香蕉蛛基象甲(Cosmopolites sordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hypera posttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenuespp.),粉蠹(Lyctus spp.),Meligethes aeneus,蛛甲属(Ptinusspp.),金黄蛛甲(Niptus hololeucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebrio molitor),扣甲属(Agriotes spp.),金针虫属(Conoderus spp.),Melolonthameiolontha,六月金龟子(Amphimallon solstitialis)和Costelytrazealandica;膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomoriumpharaonis),和胡蜂(Vespa spp.);双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydodermaspp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyia hyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipula paludosa);蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis)和角叶蚤属(Ceratophyllus spp.);蛛形纲(Arachnida),例如Scopio maurus和黑寡妇球腹蛛(Latrodectusmactans);蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssusgallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptesspp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.)。
寄生植物线虫包括例如短体线虫属(Pratylenchus spp.),相似穿孔线虫(Radopholus similis),起绒草茎线虫(Ditylenchusdipsaci),半穿刺线虫(Tylenchulus semipenetrans),异皮线虫属(Heterodera spp.),异皮线虫属(Globodera spp.),根结线虫属(Meloidogyne spp.),滑刃线虫属(Aphelenchoides spp.),长针线虫属(Longidorus spp.),剑线虫属(Xiphinema spp.)和毛刺线虫属(Trichodorus spp.)。
可以根据本发明使用的化合物用来防治对植物有害的螨虫,例如抗红叶螨(Tetranychus urticae),或者用来防治对植物有害的昆虫,例如抗菜蛾(Plutella maculipennis)的merpacatilis,辣根猿叶甲(Phaedon cochleariae)的幼虫,和黑尾叶蝉(Nephotettiixcincticeps)具有特别好的结果。
可以根据本发明使用的化合物不仅作用于植物,卫生领域和储存产品害虫有活性,而且还用于兽药领域,杀动物寄生虫(定居寄生虫),例如硬蜱,软蜱,马痒螨,恙螨,蝇(叮和吮),寄生蝇幼虫,虱,头虱,皮革虱和蚤。这样的寄生虫包括:
来自虱目(Anolpurida),例如,血虱属(Haematopinus spp.),长颚虱(Linognathus spp.),虱属(Pediculus spp.),阴虱属(Phtirusspp.),和管虱属(Solenopotes spp.)。
来自食毛目咬虱(Mallophagida)和Amblycerina及Ischnocerina亚目,例如毛羽虱属(Trimenopon spp.),Menopon spp.,巨羽虱属(Trinoton spp.),牛羽虱属(Bovicola spp.),Werneckiella spp.,Lepikentron spp.,Damalina spp.,Trichodectes spp.,Felcolaspp.。
来自双翅目(Diptera)和长角亚目(Nematocerina)和Brachycerina亚目,例如伊蚊(Aedes spp.),斑按蚊属(Anopheles spp.),库蚊(Culex spp.),蚋属(Simulium spp.),全毛真蚋(Eusimulium spp.),白蛉(Phlebotomus spp.),罗蛉属(Lutzomyia spp.),库蠓(Culicoidesspp.),斑虻(Chrysops spp.),瘤虻(Hybomitra spp),Atylotus spp.,虻属(Tabanus spp.),麻虻属(Haematopota spp.),Philipomyia spp.,Braula spp.,Musca spp.,齿股蝇属(Hydrotuea spp.),螫蝇(Stomoxysspp.),Haematobia spp.,Morellia spp.,厕蝇(Fannia spp.),Glossinaspp.,Calliphora spp.,Lucilia spp.,Chrysomyia spp.,Wohlfahrtiaspp.,别麻蝇(Sarcophaga spp.),Oestrus spp.,皮蝇(Hypodermaspp.),Gasterophilus spp.,虱蝇(Hippobosca spp.),Lipoptenaspp.,和Melophagus spp.。
来自蚤目(Siphonapterida),例如,蚤属(Pulex spp.),Ctenocephalides spp.,鼠蚤(Xenopsylla spp.),和角叶蚤(Ceratophyllus spp.)。
来自异翅亚目(Heteropterida),例如,臭虫属(Cimex spp.),吸血猎蝽属(Triatoma spp.),Rhodnius spp.,和全圆蝽属(Panstrongylus spp.)。
来自非蠊目(Blattarida),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),德国小蠊(Blattela germanica)和非蠊属(Supella spp.)。
螨亚类(Acarida)和后胸气门目(Metastigmata)和中胸气门目(Mesostigmata),例如,隐喙蜱属(Argas spp.),喙蜱属(Ornithodorusspp.),耳残喙蜱(Otabius spp.),硬蜱(Ixodes spp.),花蜱属(Amblyomma spp.),牛蜱属(Boophilus spp.),矩头蜱(Dermacentorspp.),Haemophysalis spp.,璃眼蜱(Hyalomma spp.),头蜱属(Rhipicephalus spp.),鸡皮刺螨(Dermanyssus spp.),瑞立绦虫(Raillietia spp.),Pneumonyssus spp.,Sternostoma spp.,和Varroaspp.。
来自Actinedida(恙螨亚目,Prostigmata)和Acaridida(Astigmata),例如Acarapis spp.,姬螯螨属(Cheyletiella spp.),Ornithocheyletia spp.,Myobia spp.,疥螨(Psorergates spp.),蠕形螨(Demodex spp.),恙螨(Trombicula spp.),Listrophorus spp.,粗脚粉螨(Acarus spp.),酪螨(Tyrophagus spp.),嗜木螨(Caloglyphusspp.),Hypodectes spp.,翼衣螨属(Pterolichus spp.),恙螨(Psoroptes spp.),恙螨(Chorioptes spp.),Otodectes spp.,疥螨(Sarcoptes spp.),Notoedres spp.,足螨(Knemidocoptesspp.,),Cytodites spp.,和Laminosioptes spp.。
根据本发明的活性化合物也适合提高产率。此外,它们具有低的毒性并且为植物所耐受。
根据其特殊的物理和/或化学性质,本发明活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉末剂、泡沫剂、糊剂、颗粒剂、气雾剂和包裹在聚合物中和用于种子的包被组合物中的细微胶囊,以及ULV冷雾和暖雾制剂。
这些制剂可以用已知的方式制备,例如,将活性化合物与扩充剂即液体溶剂,加压液化气体和/或固体载体混合,任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。如果使用的扩充剂是水,则也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃类,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲亚砜,还有水。液化气体扩充剂或载体理解为指常温常压下是气体的液体,例如气雾抛射剂,例如卤代烃类,或者还有丁烷,丙烷,氮和二氧化碳。合适的固体载体是:例如磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐。用于颗粒剂的适合的固体载体是:例如压碎和分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,或者还有有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳,玉米穗轴和烟茎。适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,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,芳基磺酸盐或者还有蛋白质水解产物;适合的分散剂是:例如,木素亚硫酸盐废液和甲基纤维素。
制剂中,可以使用增粘剂,如羧甲基纤维素、天然和合成的粉状、颗粒或乳胶形式的聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,或者还有天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它可能的添加剂是矿物油和植物油。
可以使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和痕量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
根据其特殊的物理和/或化学性质,本发明活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉末剂、泡沫剂、糊剂、颗粒剂、气雾剂和包裹在聚合物中和用于种子的包被组合物中的细微胶囊,以及ULV冷雾和暖雾制剂。
本发明活性化合物本身或它们的制剂也可以与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂混合使用,以例如扩大作用谱或者防止抗药性产生。在很多情况下实现增效作用,即混合物的活性超过了各个组分的活性。
混合物中共同成分的例子是下面的化合物:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoptim,敌菌灵,戊环唑,嘧菌酯,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacril-isobutyl,双丙氨酰磷,乐杀螨,bion,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,嘧菌环胺,酯菌胺,
咪菌威,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,氟环唑,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,腈苯唑,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,氟喹唑,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,种菌唑,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如: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液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,叶菌唑,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,酞菌酯,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,嘧霉胺,咯喹酮,氯吡呋醚,
quinconazole,五氯硝基苯(PCNB),quinoxyfen,
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,噻呋酰胺,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,灭菌唑,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
氰菌胺,代森锌,福美锌,还有
Dagger 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-β-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-α-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}-氨基甲酸异丙酯,
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-[(二碘代甲基)-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-吡咯烷酮,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-N-碳酰苯胺,
2,6-二氯-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-(甲硫基)-4-嘧啶基-硫代氰酸酯,
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-(2,3,3-三碘代-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-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-α-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-(溴代甲基)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-(异硫代氰酰甲基)-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-异噁唑啉基]-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-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-硫代苯二羧酸酯,
顺-1-(4-氯代苯基)-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-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-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-噁唑啉基)-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-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲烷亚氨酰胺,
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,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
bromopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,Acetamiprid,氟酯菊酯,棉铃威,涕灭威,氧涕灭威,甲体氯氰菊酯(Alpha-cypermethrin,Alphamethrin),双虫脒,avermectin,AZ60541,azadirachtin,甲基吡噁磷,azinphos-A,保棉磷,三唑锡,
日本甲虫芽孢杆菌(Bacillus popilliae),球形芽孢杆菌(Bacillussphaericus),枯草芽孢杆菌(Bacillus subtilis),苏云金芽孢杆菌(thuringiensis),Baculoviren,蚕白僵菌(Beauveria bassiana),纤细白僵菌(Beauveria tenella),噁虫威,丙硫克百威,杀虫磺,苯螨特,氟氯氰菊酯,Bifenazate,氟氯菊酯,Bioethanomethrin,生物氯菊酯,BPMC,brofenprosA,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫百克威,杀螟丹,Chloethocarb,氯氧磷,Chlorfenapyr,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,Chlovaporthrin,顺式-苄呋菊酯,顺式氯菊酯,clocythrin,除线威,四螨嗪,杀螟腈,Cycloprene,乙氰菊酯,氟氯氰菊酯-β,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,杀螨隆,二嗪磷,敌敌畏,除虫脲,乐果,甲基毒虫畏,苯虫醚,乙拌磷,docusat-sodium,dofenapyn,
克瘟散,emamectin,烯炔菊酯,硫丹,Entomopfthora spp.,高氰戊菊酯,乙硫苯威,乙硫磷,灭线磷,醚菊酯,醚菊酯,乙嘧硫磷,虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,苯硫威,Fenoxacrim,双氧威,氯氰菊酯,fenpyrad,Fenpyrithrin,唑螨酯,氰戊菊酯,氟虫腈,氟定胺,啶蜱脲,Flubrocythrinate,氟螨脲,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,
Granulosis viruses,
Halofenozide,HCH,庚烯磷,氟铃脲,噻螨酮,烯虫乙酯,
吡虫啉,氯唑磷,异丙胺磷,噁唑磷,ivermectin,
Nuclear polyhedrosis viruses,
氯氟氰菊酯,虱螨脲,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,Metharhiziumanisopliae,Metharhizium flavoviride,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,
二溴磷,烯啶虫胺,Nithiazine,Novaluron,
氧乐果,杀线威,亚砜吸磷,
玫烟色拟青霉(Paecilomyces fumosoroseus),对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,嘧啶磷-A,嘧啶磷-M,丙溴磷,猛杀威,残杀威,丙硫磷,发果,吡蚜酮,吡唑硫磷,pyresmethrin,除虫菊酯,哒螨酮,Pyridathion,嘧螨醚,蚊蝇醚,
喹硫磷,
Ribavirin,
蔬果磷,sebufos,氟硅菊酯,Spinosad,治螟硫磷,甲丙硫磷,
氟胺氰菊酯,虫酰肼,吡螨胺,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,theta-cypermethrin,thiamethoxam,蛾蝇腈,Thiatriphos,Thiocyclam hydrogen oxalate,硫双威,久效磷,thuringiensin,二甲硫吸磷,虫线磷,四溴菊酯,苯噻螨,三唑磷,triazuron,Trichlophenidine,敌百虫,杀虫隆,混灭威,
芽灭多,Vaniliprole,Verticillium lecanii,
Yl5302,
Zeta-cypermethrin,Zolaprofos,
环丙烷羧酸(1R-顺式)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)-亚呋喃基)-甲基]-2,2-二甲酯,
环丙烷羧酸(3-苯氧基苯基)-甲基-2,2,3,3-四甲酯,
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-氟代苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰氧基)-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,
氨基甲酸3-甲基苯基丙酯,
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,
苏云金芽孢杆菌菌株EG-2348,
苯甲酰2-苯甲酰基-1-(1,1-二甲基乙基)-肼,
丁酸2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4,5]十二烷-3-烯-4-酯,
[3-[(6-氯-3-吡啶基)甲基]-2-亚噻唑烷基]-氨腈,
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-肼二硫代酰胺,
N-甲基-N’-2-丙烯基-1,2-肼二硫代酰胺,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸酯。
也可以是与其它已知的活性化合物例如除草剂,或者与化肥和生长调节剂的混合物。
活性化合物可以以其自身,或者以其制剂形式或者以从中制备的使用形式使用,例如即用型溶液,混悬剂,可湿粉剂,糊剂,可溶粉剂,细粉剂和颗粒剂。以常规方法使用,例如通过浇灌,喷雾,弥雾,散播,撒细粉,发泡,刷涂在其上等。还能通过超低体积方法施用活性化合物,或者将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
当使用根据本发明的活性化合物作为杀真菌剂时,施用比例可以在相当宽的范围内变化,这取决于施用类型。处理植物部分时,活性化合物施用比例一般是0.1和10000g/ha之间,优选在10-1000g/ha之间。在处理种子时,活性化合物施用比例一般是每千克种子用0.001-50g,优选0.01-10g。处理土壤情况时,活性化合物施用比例一般是0.1和10000g/ha之间,优选在1和5000g/ha之间。
用来保护工业材料的组合物一般以1-95%重量比的量,优选10-75%重量比的量含有活性化合物。
根据本发明的活性化合物的使用浓度取决于要控制的微生物的类型和发生,并且取决于要保护的材料的组成。最佳施用量可以通过试验系列确定。一般情况下,使用浓度在以要保护的材料为基础的0.001-5%重量比范围内,优选0.05-1.0%重量比。
如果任选地加入抗微生物化合物,杀真菌剂,杀细菌剂,除草剂,杀昆虫剂或者其它活性化合物以扩大作用谱或者获得特殊效果,例如另外的抗昆虫的保护作用的,可以提高根据本发明要在材料保护中使用的活性化合物,或组合物,浓缩物或者从中制备的很一般的制剂的活性和活性范围。这些混合物可以具有比本发明化合物更广范围的作用。
当用来抗动物害虫时,根据本发明的化合物也可以以商售制剂和从这些制剂制备的使用形式与增效剂混合使用。增效剂是这样的化合物,它本身没有活性作用,但它可以提高活性化合物的活性作用。
从商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。所述使用形式的活性化合物浓度可以是0.0000001-95%重量的活性化合物,优选0.0001和1%重量。
以适合使用形式的常规方法进行施用。
根据本发明的化合物的制备和应用通过下面的实施例详细说明。制备实施例
将0.9g(2.2mmol)的5-[(4-乙酰基-苯基)-乙酰基氨基]-4-氯-3-甲基-异噻唑,0.35g(2.6mmol)的1,2-癸二醇,10mg的苯磺酸,2.0g的分子筛(3A)和15ml的甲苯的混合物在回流下加热18小时。冷却到室温后,依次用水和饱和的碳酸氢钠水溶液洗涤反应混合物。减压浓缩有机相。得到0.92g(理论量的90%)的固体,由60∶40比例的上面给出的结构式的化合物的两种异构体组成。
log p(pH2.3)=5.84和6.05起始物的制备
室温下和搅拌下,向7.0g(47.1mol)的5-氨基-4-氯-3-甲基-异噻唑和150ml的二氯甲烷的混合物中依次加入8.4g(47.1mmol)的4-乙酰基-苯乙酸和10.1g(47.1mmol)的二环己基碳化二亚胺。该反应混合物在室温下搅拌18小时。吸滤沉淀出的固体,并且减压浓缩滤液。使用环己烷/乙酸乙酯=1∶1的流动相在硅胶上层析留下的产物。浓缩洗脱液,得到11.8g(理论量的81%)的固体形式的5-[(4-乙酰基苯基)-乙酰基氨基]-4-氯-3-甲基-异噻唑。
log p(pH2.3)=2.12
*)所有情况下,存在异构体混合物。各种情况下所陈述的是较高的log p值。表14
*)所有情况下,存在异构体混合物。各种情况下所陈述的是较高的log p值。起始物的制备实施例29
室温下和搅拌下,向50ml的二氯甲烷中的4.6g(40mmol)的5-氨基-3-甲基-1,2,4-噻二唑和12.8g(162mmol)的吡啶的混合物中加入20ml二氯甲烷中的7.9g(40mmol)的3-乙酰基-苯乙酰氯。该反应混合物在室温下搅拌16小时,与20mg的4-二甲基氨基吡啶混合,并且在室温下又搅拌24小时。反应溶液然后用1N-HCl洗涤,硫酸钠干燥,并且减压浓缩。得到的残余物用乙醚研磨,得到5.5g(理论量的50%)的固体形式的5-[(3-乙酰基苯基)-乙酰基氨基]-3-甲基-1,2,4-噻二唑。
m.p.91-98℃
log P(pH2.3)=1.56
在0℃至10℃和搅拌下,向100ml的二氯甲烷中的10.3g(80mmol)的5-氨基-3-乙基-1,2,4-噻二唑,25.6g(324mmol)的吡啶和40mg的4-二甲基氨基吡啶的混合物中加入40ml二氯甲烷中的15.7g(80mmol)的3-乙酰基-苯乙酰氯。该反应混合物在室温下搅拌16小时,然后用1N-HCl洗涤,硫酸钠干燥,并且减压浓缩。得到的残余物用乙醚研磨,得到15.8g(理论量的68.4%)的固体形式的5-[(3-乙酰基苯基)-乙酰基氨基]-3-乙基-1,2,4-噻二唑。
m.p.121-125℃
log P(pH2.3)=1.87
实施例31
在0℃至10℃和搅拌下,向100ml的二氯甲烷中的11.9g(80mmol)的5-氨基-4-氯-3-甲基-异噻唑,25.6g(324mmol)的吡啶和40mg的4-二甲基氨基吡啶的混合物中加入40ml二氯甲烷中的15.7g(80mmol)的3-乙酰基-苯乙酰氯。该反应混合物在室温下搅拌16小时,然后用1N-HCl洗涤,硫酸钠干燥,并且减压浓缩。得到的残余物用乙醚研磨,得到16.9g(理论量的69%)的固体形式的5-[(3-乙酰基苯基)-乙酰基氨基]-4-氯-3-甲基-异噻唑。
m.p.77-83℃
log P(pH2.3)=2.14应用实施例
实施例A霉病(Plasmopara)试验(葡萄栽培)/保护性的溶剂: 47份重量的丙酮乳化剂: 3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将浓缩物稀释到期望的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂喷雾幼嫩植物。喷雾层风干后,用葡萄生单轴霉(Plasmopara viticola)孢子水悬浮液接种植物,并且放在大约20℃且100%相对空气湿度的培养室中一天。接着植物放置在大约21℃且相对空气湿度是大约90%的温室中5天。然后将植物弄湿并且放置在培养室中一天。
接种后6天进行评价。0%表示相当于对照物的药效,而100%的药效表示没有发现感染。下面表中给出了活性化合物,施用比例和试验结果。表A霉病试验(葡萄栽培)/保护性的表A(续)霉病试验(葡萄栽培)/保护性的表A(续)霉病试验(葡萄栽培)/保护性的
实施例B柄球菌(Podosphaera)试验(苹果)/保护性的溶剂: 47份重量的丙酮乳化剂: 3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将浓缩物稀释到期望的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂喷雾幼嫩植物。喷雾层风干后,苹果霉苹果白粉病柄球菌(Podosphaeraleucotricha)病原微生物的分生孢子接种植物。然后植物放置在大约23℃且相对空气湿度是大约70%的温室中。
接种后10天进行评价。0%表示相当于对照物的药效,而100%的药效表示没有发现感染。
实施例C白粉病(Erysiphe)试验(小麦)/保护性的溶剂: 25份重量的N,N-二甲基乙酰胺乳化剂: 0.6份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将浓缩物稀释到期望的浓度。
为了试验保护活性,以所述施用比例,用活性化合物制剂喷雾幼小植物。
喷雾层风干后,将麦类白粉病(Erysiphe graminis f.sp.tritici)的孢子撒在植物上。
植物放置在温度大约20℃且相对空气湿度是大约80%的温室中以促进霉色点的生长。
接种后7天进行评价。0%表示相当于对照物的效力,而100%的效力表示没有发现感染。
实施例D叶蝉(Nephotettix)试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量溶剂和所述量乳化剂混合,用水将浓缩物稀释到期望的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理稻苗(Oryzasativa),并在籽苗还湿润的时候用黑尾叶蝉(Nephotettixcincticeps)的幼虫定居。
一定时间后,测定杀伤百分率。100%表示所有的叶蝉都已经被杀死;0%表示没有杀死一只叶蝉。
下面的表中给出了活性化合物,施用比例和试验结果。
表D
伤害植物的昆虫
叶蝉试验实施例E猿叶甲(Phaedon)幼虫试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量溶剂和所述量乳化剂混合,用水将浓缩物稀释到期望的浓度。
通过浸入到活性化合物的制剂中来处理甘蓝叶(Brassicaoleracea),并且在叶子还湿润的时候用辣根猿叶甲(Phaedoncochleariae)幼虫定居。
一定时间后,测定杀伤百分率。100%表示所有的甲虫幼虫都已经被杀死;0%表示没有杀死一只甲虫幼虫。
下面的表中给出了活性化合物,施用比例和试验结果。表E伤害植物的害虫猿叶甲幼虫试验表E(续)伤害植物的害虫猿叶甲幼虫试验实施例F草地粘虫(Spodoptera frugiperda)试验溶剂: 7份重量的二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量溶剂和所述量乳化剂混合,用水将浓缩物稀释到期望的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用草地粘虫(Spodoptera frugiperda)毛虫定居。
一定时间后,测定杀伤百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
实施例G叶螨(Tetranychus)试验(OP-抗性/浸入处理)溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量溶剂和所述量乳化剂混合,用含有乳化剂的水将浓缩物稀释到期望的浓度。
将严重侵染有所有发育阶段的棉叶螨(Tetranychus urticae)的大豆植物(Phaseolus vulgaris)浸入到期望浓度的活性化合物的制剂中。
一定时间后,测定活性百分率。100%表示所有的叶螨都已经被杀死;0%表示没有杀死一只叶螨。
下面的表中给出了活性化合物,施用比例和试验结果。表G伤害植物的昆虫叶螨试验(OP-抗性/浸入处理)
Claims (10)
1.下式的苯基乙酸杂环基酰胺其中R1代表烷基,卤代烷基,烷氧基烷基,烷硫基烷基,烷氧基,烷硫基或者代表任选被取代的环烷基,R2代表氢,烷基羰基,烷氧羰基或者代表各自任选被取代的芳基羰基,芳基氧基羰基或芳烷基氧基羰基,R3代表氢或烷基,R4代表任选被取代的烷基,任选被取代的链烯基,任选被取代的炔烃基,任选被取代的芳基,任选被取代的芳烷基,任选被取代的芳烷基氧基或者代表任选被取代的芳烷基氧基烷基,或者两个成对的或连位的R4基团与它们连接的碳原子一起形成饱和的或不饱和的,任选被取代的其中可包含一个或两个杂原子的5-或6-元环,n代表1-4的整数,X代表氮原子或者代表下式基团CH,C-Cl,C-Br,C-C≡CH,C-CN或
和A代表一个直接的键或一个CH2基团。
3.防治不期望的微生物和动物害虫的组合物,特征在于,它们含有至少一种权利要求1的式(I)的苯基乙酸杂环基酰胺,和扩充剂和/或表面活性剂。
4.权利要求1的式(I)的苯基乙酸杂环基酰胺防治不期望的微生物和动物害虫的用途。
5.防治不期望的微生物和动物害虫的方法,特征在于,对不期望的微生物和动物害虫和/或它们的栖息地施用权利要求1的式(I)的苯基乙酸杂环基酰胺。
6.制备防治不期望的微生物和动物害虫的组合物的方法,特征在于,将权利要求1的式(I)的苯基乙酸杂环基酰胺与扩充剂和/或表面活性剂混合。
8.制备权利要求7的式(II)的氨基衍生物的方法,特征在于c)使式(V)的杂环基-胺其中R1和X如上定义,进行下面的反应之一:α)任选地在酸结合剂的存在下和任选地在稀释剂的存在下与式(VI)的酰基卤反应其中R3如上定义和Hal1代表氯或溴,或者β)在催化剂的存在下和在稀释剂的存在下,与式(VII)的苯基乙酸衍生物反应其中R3如上定义。
10.权利要求1的苯基乙酸杂环基酰胺,特征在于具有下面的结构式下式
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US7244853B2 (en) | 2001-05-09 | 2007-07-17 | President And Fellows Of Harvard College | Dioxanes and uses thereof |
WO2005040143A1 (en) * | 2003-10-27 | 2005-05-06 | Basf Aktiengesellschaft | 5-(2-arylacetamido)isothiazole compounds ii |
JP5744376B2 (ja) | 2005-03-22 | 2015-07-08 | プレジデント アンド フェローズ オブ ハーバード カレッジ | タンパク質分解障害の治療 |
JP5409015B2 (ja) | 2006-02-14 | 2014-02-05 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | ヒストンデアセチラーゼ阻害剤 |
CN101400362B (zh) | 2006-02-14 | 2016-10-12 | 哈佛大学校长及研究员协会 | 双官能组蛋白去乙酰化酶抑制剂 |
CN101484156B (zh) | 2006-05-03 | 2015-11-25 | 哈佛大学校长及研究员协会 | 组蛋白脱乙酰基酶和微管蛋白脱乙酰基酶抑制剂 |
RU2515611C2 (ru) | 2008-07-23 | 2014-05-20 | Президент Энд Феллоуз Оф Гарвард Колледж | Ингибиторы деацетилазы и их применение |
WO2011019393A2 (en) | 2009-08-11 | 2011-02-17 | President And Fellows Of Harvard College | Class- and isoform-specific hdac inhibitors and uses thereof |
WO2014002106A1 (en) * | 2012-06-25 | 2014-01-03 | Cadila Healthcare Limited | Novel compounds for the treatment of dyslipidemia and related diseases |
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Publication number | Priority date | Publication date | Assignee | Title |
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BE790010A (fr) | 1971-10-15 | 1973-04-12 | Fmc Corp | Herbicides nouveaux |
US4895849A (en) | 1986-10-08 | 1990-01-23 | Ube Industries, Ltd. | Aralkylaminopyrimidine compounds which are useful as for producing thereof and insecticides |
DE3864839D1 (de) | 1987-01-19 | 1991-10-24 | Ciba Geigy Ag | Substituierte dioxolanderivate. |
GB9008123D0 (en) | 1990-04-10 | 1990-06-06 | Lilly Industries Ltd | Pharmaceutical compounds |
TW231257B (zh) | 1992-03-02 | 1994-10-01 | Ciba Geigy | |
BR9305466A (pt) | 1992-03-26 | 1994-12-20 | Dowelanco | Nitroanilinas n-heterocíclicas usadas como fungicidas |
WO1994021617A1 (en) | 1993-03-19 | 1994-09-29 | Dowelanco | A process for preparing halogenated isothiazoles |
JPH072604A (ja) | 1993-05-05 | 1995-01-06 | Shell Internatl Res Maatschappij Bv | 殺虫方法および農薬化合物 |
DE4328425A1 (de) | 1993-08-24 | 1995-03-02 | Basf Ag | Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung |
ES2138653T3 (es) | 1993-12-30 | 2000-01-16 | Novartis Ag | Eteres fenilicos substituidos. |
CA2189573A1 (en) | 1994-05-17 | 1995-11-23 | Ronald E. Hackler | N-(5-isothiazolyl)amide pesticides |
DE19542372A1 (de) * | 1995-11-14 | 1997-05-15 | Bayer Ag | Acylierte 5-Aminoisothiazole |
DE19601139A1 (de) | 1996-01-15 | 1997-07-17 | Bayer Ag | Acylierte 5-Amino-1,2,4-thiadiazole |
DE19628569A1 (de) * | 1996-07-16 | 1998-01-22 | Bayer Ag | Substituierte N-(5-Isothiazolyl)-thioamide |
DE19630814A1 (de) | 1996-07-31 | 1998-02-05 | Bayer Ag | Substituierte N-Isothiazolyl-(thio)amide |
DE19715017A1 (de) | 1997-04-11 | 1998-10-15 | Bayer Ag | Substituierte Aryluracile |
-
1998
- 1998-10-06 DE DE19846008A patent/DE19846008A1/de not_active Withdrawn
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- 1999-09-23 JP JP2000574527A patent/JP2002526541A/ja active Pending
- 1999-09-23 KR KR1020017003662A patent/KR20010079897A/ko not_active Application Discontinuation
- 1999-09-23 US US09/806,430 patent/US6403622B1/en not_active Expired - Fee Related
- 1999-09-23 CN CN99814170A patent/CN1329611A/zh active Pending
- 1999-09-23 WO PCT/EP1999/007105 patent/WO2000020415A1/de not_active Application Discontinuation
- 1999-09-23 AU AU61958/99A patent/AU6195899A/en not_active Abandoned
- 1999-09-23 EP EP99948849A patent/EP1119569A1/de not_active Withdrawn
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JP2002526541A (ja) | 2002-08-20 |
AU6195899A (en) | 2000-04-26 |
EP1119569A1 (de) | 2001-08-01 |
DE19846008A1 (de) | 2000-04-13 |
KR20010079897A (ko) | 2001-08-22 |
WO2000020415A1 (de) | 2000-04-13 |
US6403622B1 (en) | 2002-06-11 |
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