CN102256491A - 用作杀真菌剂的异噁唑衍生物 - Google Patents
用作杀真菌剂的异噁唑衍生物 Download PDFInfo
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- CN102256491A CN102256491A CN2009801507449A CN200980150744A CN102256491A CN 102256491 A CN102256491 A CN 102256491A CN 2009801507449 A CN2009801507449 A CN 2009801507449A CN 200980150744 A CN200980150744 A CN 200980150744A CN 102256491 A CN102256491 A CN 102256491A
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000005962 plant activator Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
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- 229920002647 polyamide Polymers 0.000 description 1
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- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Communicable Diseases (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及具有杀真菌活性的式(I)异噁唑化合物,涉及包含它们的农业组合物,并且涉及所述化合物和组合物在农业中用于防治植物上的微生物病害,特别是真菌病害的用途。
Description
本发明涉及具有杀真菌活性的异噁唑化合物,涉及包含它们的农业组合物,并且涉及所述化合物和组合物在农业中用于防治植物上的微生物病害,特别是真菌病害的用途。
严重真菌感染的发生率,无论是系统性还是局部性的,都在植物、动物和人类中持续增长。许多真菌是环境中所常见的并且对植物和哺乳动物无害。然而,某些真菌可以在植物、人类和/或动物中导致疾病。
杀真菌剂是天然或合成来源的化合物,其保护植物对抗由真菌包括卵菌纲(oomycetes)引起的损害。目前的农业方法非常依赖于杀真菌剂的使用。事实上,某些作物的有用生长离不开杀真菌剂的使用。使用杀真菌剂使得生产者可以增加作物产量,并且作为结果增加作物价值。已经开发出许多杀真菌剂。然而,对真菌侵袭和感染的处理一直是重大问题。此外,对杀真菌剂和抗真菌药的抗性已成为严重的问题,其使得这些试剂对某些农业和治疗用途无效。因此,需要开发新的杀真菌和抗真菌化合物(参见,例如US专利号6,673,827;还参见Walter的US专利号6,617,330,其描述作为杀真菌剂的嘧啶-4-烯胺)。
国际专利申请WO2006/031631提及具有杀真菌特性的一系列异噁唑衍生物。因此,需要防治真菌的备择方法。优选,新的化合物可以具有改善的杀真菌特性,比如改善的效力、改善的选择性、产生抗性的倾向较低或者对较宽真菌谱的活性。化合物可以更有利地配制或提供更有效的递送和在作用场所的保留,或者可以更容易地生物降解。有利的化合物或其降解组分一般可以是毒性更低的。
已令人惊讶地发现本发明的异噁唑化合物展示出乎意料的杀真菌活性,并因此适于用在农业中作为作物保护试剂以抗击或预防真菌侵袭,或防治对作物有害的其它病虫害比如杂草、昆虫或螨类。
相应地,在第一方面中,本发明提供式(I)化合物
其中R1是H或酰基,优选H;
或其农业化学上可接受的盐。
酰基包括任意易水解的酰基,并包含例如,C(O)R2,C(O)OR2,C(O)NHR2和C(O)NR2R3,其中R2和R3各自独立选自烷基,烯基,炔基,杂环基,芳基和杂芳基。酰基可以任选用一个或多个例如1、2、3或4个卤素或OR2基团取代。优选的酰基是乙酰基,苯甲酰基和苯乙酰基。
烷基可以直链的、支化的或环状的并且含有1至24个碳原子。优选的烷基可以含有1至10个碳原子,更优选1至6碳,甚至更优选1至4个碳原子。代表性的烷基包括,例如甲基,乙基,异丙基,正丙基,正丁基,叔丁基,叔戊基,2,5-二甲基己基,环丁基,环丙基,环戊基和环己基。
杂环基可以含有3至10环原子,其中多至4个可以是杂原子比如氮、氧和硫,并且可以是饱和的或部分不饱和的。杂环基的实例是环氧乙烷基,氮杂环丁烷基,四氢呋喃基,硫杂环戊基,吡咯烷基,吡咯啉基,咪唑烷基,咪唑啉基,环丁砜基,二氧杂环戊基,二氢吡喃基,四氢吡喃基,哌啶基,吡唑啉基,吡唑烷基,二噁烷基,吗啉基,二噻烷基,硫吗啉基,哌嗪基,氮杂基,氧氮杂基,硫氮杂基,噻唑啉基和二氮杂环庚烷基。
芳基包括苯基,萘基,蒽基和菲基。
杂芳基可以含有3至10环原子,其中多至4个可以是杂原子比如氮、氧和硫。杂芳基的实例是呋喃基,噻吩基,吡咯基,噁唑基,噻唑基,咪唑基,吡唑基,异噁唑基,异噻唑基,噁二唑基,三唑基,噻二唑基,吡啶基,嘧啶基,吡嗪基,哒嗪基,四唑基,三嗪基。此外,术语杂芳基包括稠合的杂芳基,例如苯并咪唑基,苯并噁唑基,咪唑并吡啶基,苯并噁嗪基,苯并噻嗪基,噁唑并吡啶基,苯并呋喃基,喹啉基,喹唑啉基,喹喔啉基,苯并噻唑基,酞酰亚氨基,苯并呋喃基,苯并二氮杂基,吲哚基和异吲哚基。
卤代意指氟,氯,溴或碘。
本发明化合物包括如前文所定义的式(I)化合物,其多晶型和异构体,包括旋光、几何和互变异构体,以及同位素标记的式(I)化合物。
农业化学上可接受的盐具有农业或园艺用途的成盐领域中已知和接受的阳离子。优选,所述盐是可溶于水的。
式(I)化合物的适宜盐包括酸加成盐,例如与无机酸比如盐酸,氢溴酸,硫酸,硝酸或磷酸形成的那些,或者与有机羧酸比如草酸,酒石酸,乳酸,丁酸,甲苯酸,己酸或邻苯二甲酸,或者与磺酸比如甲磺酸,苯磺酸或甲苯磺酸形成的那些。有机羧酸的其他实例包括卤代酸,比如三氟乙酸。
N-氧化物是叔胺的氧化形式或者含氮杂芳族化合物的氧化形式。它们描述于许多书籍中,例如Angelo Albini和Silvio Pietra的“Heterocyclic N-oxides”,CRC Press,Boca Raton,佛罗里达,1991。
在一种优选实施方式中,本发明提供组合物,其包含式(I)化合物,或其农业化学上可接受的盐,和农业化学上可接受的稀释剂或载体。本文提及本发明化合物之处应视为包括式(I)化合物及其农业化学上可接受的盐。
式(I)化合物作为包含(R)和(S)-对映体的外消旋体存在。已发现(S)-对映体具有与(R)-对映体相比显著更高的杀真菌活性。
因此,在优选的方面,本发明还提供式(I)化合物的(S)-对映体
其中R1是H或酰基,优选H;
或其农业化学上可接受的盐。
因此,在优选的方面,提供组合物,其包含式(S)-(I)化合物,或其农业化学上可接受的盐,和农业化学上可接受的稀释剂或载体。
优选地,作为单个对映体提供的式(S)-(I)化合物具有的对映体过量(e.e.)为至少40%,例如至少50%、60%、70%或80%,优选至少90%,更优选至少95%,还更优选至少98%并且最优选至少99%。
最优选地,式(I)化合物是(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇(实施例2)
或其农业化学上可接受的盐。
优选地,作为单个对映体提供的实施例2化合物具有的对映体过量(e.e.)为至少40%,例如至少50%、60%、70%或80%,优选至少90%,更优选至少95%,还更优选至少98%并且最优选至少99%。
本发明的化合物和组合物用于保护植物对抗由真菌,包括卵菌纲(oomycetes),所引起的疾病。本发明化合物能够在农业领域和有关领域中用作防治植物病虫害的活性成分。本发明化合物可以被用于抑制或消灭在有用植物的不同作物的植物或植物部分(果实、花卉、叶、茎、块茎、根)上发生的病虫害,任选地同时还保护之后生长的那些植物部分,例如保护其免于致植物病性微生物。
本发明的化合物和组合物可以用作处理植物繁殖材料的拌种试剂以保护对抗真菌侵染以及对抗土壤中发生的致植物病性真菌,所述植物繁殖材料尤其是种子(果实、块茎、谷物)和植物插条(例如稻)。
在额外的方面中,本发明提供防治或预防病原微生物侵染栽培植物的方法,包括将式(I)化合物或其组合物以有效防治所述微生物的量施用至所述植物、其部分或其处所。
本发明的化合物和组合物可以用来对抗致植物病性真菌,例如下述类别的那些:半知菌类(Fungi imperfecti)(例如葡萄孢属(Botrytis),梨孢属(Pyricularia),长蠕孢属(Heiminthosporium),镰孢属(Fusarium),壳针孢属(Septoria),尾孢属(Cercospora)和链格孢属(Alternaria))和担子菌纲(Basidiomycetes)(例如丝核菌属(Rhizoctonia),驼孢锈菌属(Hemileia),柄锈菌属(Puccinia))。此外,它们还可以用来对抗子囊菌纲(Ascomycetes)(例如黑星菌属(Venturia)和白粉菌属(Erysiphe),叉丝单囊壳属(Podosphaera),链核盘菌属(Monilinia),钩丝壳属(Uncinula))和卵菌纲(Oomycetes)(例如疫霉属(Phytophthora),腐霉属(Pythium),单轴霉属(Plasmopara))。可处理的真菌的具体实例包括但不限于小麦壳针孢(Septoria tritici),颖枯壳多孢(Stagonospora nodorum),致病疫霉(Phytophthora infestans),灰葡萄孢(Botrytis cinerea),同果核盘菌(Sclerotinia homoeocarpa)和隐匿柄锈菌(Puccinia recondita)。
在本发明的优选实施方式中,本发明的化合物和组合物用来对抗真菌有机体小麦壳针孢(Septoria tritici)。
待保护的有用植物作物一般包含,例如,下述植物种类:禾谷类(小麦,大麦,黑麦,燕麦,玉米(包括饲料用玉米,爆裂种玉米和甜玉米),稻,高粱和有关作物);甜菜(糖用甜菜和饲用甜菜);豆科植物(菜豆,小扁豆,豌豆,大豆);油料植物(油菜,芥菜,向日葵);黄瓜植物(西葫芦,黄瓜,甜瓜);纤维植物(棉花,亚麻,大麻,黄麻);蔬菜(菠菜,莴苣,芦笋,卷心菜,胡萝卜,茄子,洋葱,胡椒,番茄,马铃薯,辣椒,秋葵);种植园作物(香蕉,果树,橡胶树,树木苗圃),观赏植物(花卉,灌木,阔叶树和常青树,比如针叶树);以及其它植物比如藤本植物,灌木类浆果(bushberries)(比如越桔),蔓藤类浆果(caneberries),酸果蔓,胡椒薄荷,大黄,留兰香,甘蔗和草皮草包括,例如,冷季草皮草(例如,早熟禾属(Poa L.),比如草地早熟禾(Poa pratensis L.),普通早熟禾(Poatrivialis L.),加拿大早熟禾(Poa compressa L.)和早熟禾(Poa annua L.);剪股颖属(Agrostis L.),比如匍匐翦股颖(Agrostis palustris Huds.),细弱翦股颖(Agrostis tenius Sibth.),普通翦股颖(Agrostis canina L.)和小糠草(Agrostis alba L.);羊茅属(Festuca L.),比如苇状羊茅(Festucaarundinacea Schreb.),牛尾草(Festuca elatior L.)和细叶羊茅,比如紫羊茅(Festuca rubra L.),丛生型紫羊茅(Festuca rubra var.CommutataGaud.),羊茅(Festuca ovina L.)和长叶羊茅(Festuca longifolia);和黑麦草属(Lolium L.),比如多年黑麦草(Lolium perenne L.)和多花黑麦草(Lolium multiflorum Lam.))和暖季草皮草(例如,狗牙根属(Cynodon L.C.Rich),包括杂交和普通狗牙根;结缕草属(Zoysia Willd.),偏序钝叶草(Stenotaphrum secundatum(Walt.)Kuntze);和假俭草(Eremochloaophiuroides(Munro.)Hack.))。
有用植物的作物还包括由于常规育种方法或基因工程方法使其耐受除草剂如溴苯腈或多类除草剂(比如HPPD抑制剂,ALS抑制剂;例如氟嘧磺隆,氟磺隆和三氟啶磺隆,EPSPS(5-烯醇-丙酮酰-莽草酸-3-磷酸-合成酶)抑制剂,GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)的植物。已通过常规育种方法(诱变)使其耐受咪唑啉酮类(例如甲氧咪草烟)的作物的实例是夏季油菜(Canola)。通过基因工程方法使之耐受除草剂或除草剂类的作物实例包括抗草甘膦和抗草铵膦的玉米品种,该品种可根据商品名和购得。
有用植物的作物也包括这样的植物,其已通过使用重组DNA技术转化使其能够合成一种或多种选择性作用的毒素,所述毒素比如已知自产毒素细菌,特别是芽孢杆菌属(Bacillus)的那些。
有用植物的作物也包括这样的植物,其已通过使用重组DNA技术转化使其能够合成具有选择性作用的抗病原物质,比如所谓的″发病机理-相关性蛋白″(PRPs,参见例如欧洲专利申请EP 0,392,225)。所述抗病原物质和能合成所述抗病原物质的转基因植物的实例已知于例如欧洲专利申请EP 0,392,225和EP 0,353,191以及国际专利申请WO 95/33818。所述转基因植物的制造方法是本领域技术人员通常已知的,并且描述于例如上述出版物中。
在本发明的优选实施方式中,有用植物作物选自禾谷类,稻,甜菜,豆科植物,油料植物,黄瓜植物,纤维植物,蔬菜,种植园作物,观赏植物,藤本植物,灌木类浆果(bushberries),蔓藤类浆果(caneberries),酸果蔓,胡椒薄荷,大黄,留兰香,甘蔗和草皮草。
本发明的化合物和组合物能够与其它化合物同时或依次施用至待处理的作物区域或植物。这些其它化合物可以是例如肥料或微量营养素供体或影响植物生长的其它制剂。它们还可以是选择性除草剂和杀昆虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂、植物生长调节剂、植物活化剂或数种上述制剂的混合物,视需要还与制剂领域惯用的其它载体、表面活性剂或施用促进助剂一起。
本发明化合物能够与其它杀真菌剂混合,在某些情况下这引起出乎意料的增效活性。
特别优选的混合组分是唑类比如氧环唑,联苯三唑醇,丙环唑,苯醚甲环唑,烯唑醇,环丙唑醇,氟环唑,氟喹唑,氟硅唑,粉唑醇,己唑醇,抑霉唑,亚胺唑,种菌唑,戊唑醇,四氟醚唑,腈苯唑,叶菌唑,腈菌唑,perfurazoate,戊菌唑,糠菌唑,啶斑肟,咪鲜胺,三唑酮,三唑醇,氟菌唑或灭菌唑;嘧啶基甲醇类比如环丙嘧啶醇,氯苯嘧啶醇或氟苯嘧啶醇;2-氨基-嘧啶比如乙嘧酚磺酸酯,二甲嘧酚或乙嘧酚;吗啉类比如十二环吗啉,苯锈啶,丁苯吗啉,螺环菌胺或十三吗啉;苯胺基嘧啶类比如嘧菌环胺,嘧霉胺或嘧菌胺;吡咯类比如拌种咯或咯菌腈;苯基酰胺类比如苯霜灵,呋霜灵,甲霜灵,R-甲霜灵,呋酰胺或噁霜灵;苯并咪唑类比如苯菌灵,多菌灵,咪菌威,麦穗宁或噻菌灵;二甲酰亚胺类比如乙菌利,菌核利,异菌脲,甲菌利,腐霉利或乙烯菌核利;甲酰胺类比如萎锈灵,甲呋酰胺,氟酰胺,灭锈胺,氧化萎锈灵或噻氟菌胺;胍类比如双胍辛,多果定或双胍辛胺;嗜球果伞素类(strobilurines)比如嘧菌酯,醚菌酯,苯氧菌胺,吡唑醚菌酯,啶氧菌酯,SSF-129,2[(2-三氟甲基)-吡啶-6-氧基甲基]-3-甲氧基-丙烯酸甲酯或2-[{.α.[(.α.-甲基-3-三氟甲基-苄基)亚氨基]-氧基}-邻-甲苯基]-乙醛酸-甲基酯-O-甲基肟(肟菌酯);二硫代氨基甲酸酯类比如福美铁,代森锰锌,代森锰,代森联,丙森锌,福美双,代森锌或福美锌;N-卤代甲硫基-二甲酰亚胺类比如敌菌丹,克菌丹,苯氟磺胺,氟氯菌核利(fluoromide),灭菌丹或甲苯氟磺胺;含铜化合物比如波尔多液,氢氧化铜,王铜,硫酸铜,氧化亚铜,代森锰铜或喹啉铜;硝基苯酚衍生物比如二硝基巴豆酸酯或酞菌酯;有机磷衍生物比如敌瘟磷,异稻瘟净,稻瘟灵,氯瘟磷,吡菌磷或甲基立枯磷;和多种结构的其它化合物比如活化酯,超敏蛋白(harpin),敌菌灵,灭瘟素,灭螨猛,氯苯甲醚,百菌清,霜脲氰,二氯萘醌,哒菌酮,氯硝胺,乙霉威,烯酰吗啉,二氰蒽醌,土菌灵,噁唑菌酮,咪唑菌酮,三苯锡,嘧菌腙,氟啶胺,磺菌胺,环酰菌胺,三乙膦酸铝,噁霉灵,春雷霉素,磺菌成,戊菌隆,四氯苯酞,多抗霉素,烯丙苯噻唑,霜霉威,咯喹酮,苯氧喹啉(quinoxyfen),五氯硝基苯,硫,咪唑嗪,三环唑,嗪氨灵,有效霉素,(S)-5-甲基-2-甲硫基-5-苯基-3-苯基氨基-3,5-二氢咪唑-4-酮(RPA 407213),3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧代丙基)-4-甲基苯甲酰胺(RH-7281),N-烯丙基-4,5-二甲基-2-三甲基甲硅烷基噻吩-3-甲酰胺(MON 65500),4-氯-4-氰基-N,N-二甲基-5-对-甲苯基咪唑-1-磺酰胺(IKF-916),N-(1-氰基-1,2-二甲基丙基)-2-(2,4-二氯苯氧基)-丙酰胺(AC 382042)或缬霉威(SZX 722)。
本发明化合物能够与一种或多种系统获得性抗性诱导物(″SAR″诱导物)混合,单独或与上述杀真菌剂组合。SAR诱导剂是已知的并描述于例如US专利号6,919,298。通常,SAR诱导物是能够开启植物对致病害物的抗性的任意化合物,其包括但不限于病毒、细菌、真菌,或这些物质的组合。此外,SAR诱导物可以诱导植物对昆虫摄食的抗性,如Enyedi等人(1992;Cell 70:879-886)所定义。示范性SAR诱导剂涵盖许多结构类别的化合物,但共同之处是其诱导对植物疾病和/或病虫害摄食的抗性的能力。一类SAR诱导剂是水杨酸类。商业SAR诱导剂活化酯(作为得自Syngenta),超敏蛋白(作为MessengerTM得自EdenBiosciences),来自酿酒酵母(Saccharomyces cerevisiae)的酵母提取物水解产物(作为得自佛罗里达州迈阿密的MorseEnterprises Limited,Inc.),和噻菌灵(Oryzemate)可用于本发明。激卫素,包括Goemar产品是还可以使用的又一类SAR诱导剂。此外,乙烯、其生物合成前体或释放乙烯的化合物比如Ethrel视为在该情况下有用的SAR诱导剂。
适宜的载体和助剂可以是固体或液体并且是制剂技术中有用的物质,例如天然的或经再生的矿物质、溶剂、分散剂、润湿剂、增粘剂、增稠剂、粘合剂或肥料。
施用本发明的化合物和组合物的优选方法是叶面施用。施用频率和施用率将取决于被相应病原菌侵染的风险。然而,通过用液体制剂灌注植物处所或将该化合物以固体形式,例如以颗粒形式施用至土壤(土壤施用),本发明化合物可以经由土壤通过根部透入植物(内吸作用)。在水生作物比如稻的情况下,上述颗粒能够施用至淹灌的稻田。本发明的化合物和组合物还可以这样施用至种子(包衣):用杀真菌剂的液体配制剂浸渍种子或块茎或者用固体配制剂将其包衣。
术语处所如本文所用期望包涵经处理栽培作物生长于其上的或其中已播撒栽培植物种子的大田,或者种子将置于土壤中的场所。术语种子期望包涵植物繁殖材料比如插条,幼苗,种子,和发芽的或经浸泡的种子。
术语植物繁殖材料意指植物的生殖部分,包括全部类别的种子(果实、块茎、鳞茎、谷物等),根,根茎,插条,伐条等。植物繁殖材料还可以包括植物和幼苗,其有待在萌芽之后或者自土壤出苗之后进行移植。
本发明化合物可以以未修饰形式使用或者优选与配制剂领域中常用的助剂一起使用。为此,以已知方式将它们方便地配制为颗粒剂,可湿性粉剂或可溶性粉剂,乳油,可涂覆的糊剂,粉剂,胶悬剂,可直接喷雾的或可直接稀释的溶液剂,悬浮剂或乳液剂,或者受控释放形式比如微胶囊。与组合物的类型相似地,同样根据目标对象和主要环境来选择施用方法,比如喷雾、雾化、喷粉、撒播、被覆或浇注。
本发明组合物,和如果希望的固体或液体助剂,以已知方式一般这样制备:将化合物与增量剂,例如溶剂、固体载体,和任选地表面活性化合物(表面活性剂)一起密切混合和/或研磨。
适宜的载体和助剂可以是固体或液体并且对应于配制剂技术中通常使用的物质,例如天然或再生矿物质、溶剂、分散剂、润湿剂、增粘剂、增稠剂、粘合剂或肥料。这些载体例如描述于WO 97/33890。
农业化学组合物通常包括0.1到99%重量、优选0.1到95%重量的式(I)化合物,99.9到1%重量、优选99.8到5%重量的固体或液体助剂,以及0到25%重量、优选0.1到25%重量的表面活性剂。
尽管优选将商业产品制剂为浓缩物,但终端用户一般使用稀释制剂。
该组合物还可以包含其它助剂比如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂以及肥料、微量营养素供体或其它用来获得特殊效果的配制剂。
适宜地,本发明的农业化学组合物在病害发展之前施用。配制剂的使用量和频率是本领域常规的那些,并且取决于被真菌病原物侵染的风险、植物的发育阶段和场所、时机和施用方法。有利的施用率通常是5g到2kg的活性成分(a.i.)每公顷(ha),优选10g到1kg a.i./ha,最优选20g到600g a.i./ha。当用作种子处理试剂时,适宜的施用率是10mg到1g活性成分每kg种子。
浓悬浮剂是含水配制剂,其中悬浮有活性化合物的细分固体颗粒。所述配制剂包括抗沉剂(anti-settling agents)和分散剂,并可以还包括用来增强活性的润湿剂,以及消泡剂和晶体生长抑制剂。使用时,将这些浓悬浮剂稀释于水中,并通常作为喷雾剂施用至待处理的区域。活性成分的量可以是浓悬浮剂的0.5%至95%。
可湿性粉剂是在水中或其它液体载体中易于分散的细分颗粒形式。所述颗粒包含保留在固体基质中的活性成分。典型的固体基质包括漂白土、高岭土、硅土和其它易于润湿的有机或无机固体。可湿性粉剂通常含有5%至95%的活性成分和少量润湿剂、分散剂或乳化剂。
乳油是在水中或其它液体中可分散的匀质液体组合物并可以完全由活性化合物与液体或固体乳化剂组成,或者还可以含有液体载体比如二甲苯、重芳族的石脑油、异佛尔酮和其它非挥发性有机溶剂。在使用中,将上述乳油分散在水或其它液体中并通常作为喷雾施用至待处理区域。活性成分的量可以是乳油的0.5%至95%。
颗粒配制剂包括挤出物和相对粗糙的颗粒并且通常不加稀释地施用至需要防治致植物病真菌的区域。颗粒配制剂的典型载体包括细砂,漂白土,凹凸棒石粘土,斑脱粘土,蒙脱石粘土,蛭石,珍珠岩,碳酸钙,砖,浮石,叶蜡石,高岭土,白云石,灰泥,木屑,玉米芯粉,磨碎的花生壳,糖类,氯化钠,硫酸钠,硅酸钠,硼酸钠,氧化镁,云母,氧化铁,氧化锌,氧化钛,氧化锑,冰晶石,石膏,硅藻土,硫酸钙以及吸收活性化合物或能用其包覆的其它有机或无机材料。颗粒配制剂通常含有5%至25%的活性成分,其可以包含表面活性剂如重芳族石脑油、煤油和其它石油级分,或植物油;和/或粘合剂如糊精、胶水或合成树脂。
粉尘剂是活性成分与细分固体的自由流动性混合物,所述细分固体是比如滑石、粘土、面粉和其它充当分散剂和载体的有机和无机固体。
微囊一般是包封在惰性多孔壳中的活性成分小滴或颗粒,所述惰性多孔壳使得所包封物质以受控速率释放至环境中。经包囊小滴的直径典型地为1至50微米。被包封的液体典型地构成胶囊重量的50至95%,并且除活性化合物以外还可以包含溶剂。包囊粒剂通常是具有密封颗粒孔口的多孔膜的多孔颗粒,活性成分以液体形式保留在颗粒孔中。颗粒的直径通常是1毫米到1厘米,优选1到2毫米。颗粒剂通过挤出、团聚或喷射造粒形成或是天然形成。这种材料的实例为蛭石、烧结粘土、高岭土、凹凸棒石粘土、锯屑和颗粒状碳。壳或膜材料包括天然或合成橡胶、纤维质材料、苯乙烯-丁二烯共聚物、聚丙烯腈、聚丙烯酸类、聚酯、聚酰胺、聚脲、聚氨酯和淀粉黄原酸酯。
用于农业化学应用的其它有用配制剂包括活性成分在其可以希望浓度完全溶解的溶剂中的简单溶液,所述溶剂是比如丙酮,烷基化萘,二甲苯和其它有机溶剂。还可以使用加压喷雾器,其中由于低沸点分散剂溶剂载体的汽化导致活性成分以细分形式分散。
用于将本发明组合物配制为上述配制剂类型的适宜农业助剂和载体是本领域技术人员所熟知的。
可以采用的液体载体包括,例如水,甲苯,二甲苯,石脑油,植物油,丙酮,甲乙酮,环己酮,乙酸酐,乙腈,苯乙酮,乙酸戊酯,2-丁酮,氯苯,环己烷,环己醇,乙酸烷基酯,二丙酮醇,1,2-二氯丙烷,二乙醇胺,对-二乙基苯,二乙二醇,二乙二醇松香酸酯,二乙二醇丁醚,二乙二醇乙醚,二乙二醇甲醚,N,N-二甲基甲酰胺,二甲亚砜,1,4-二噁烷,二丙二醇,二丙二醇甲醚,二丙二醇二苯甲酸酯,diproxitol,烷基吡咯烷酮,乙酸乙酯,2-乙基己醇,碳酸亚乙酯,1,1,1-三氯乙烷,2-庚酮,α蒎烯,d-柠檬烯,乙二醇,乙二醇丁醚,乙二醇甲醚,γ-丁内酯,甘油,甘油二乙酸酯,甘油单乙酸酯,甘油三乙酸酯,十六烷,己二醇,乙酸异戊酯,乙酸异冰片酯,异辛烷,异佛尔酮,异丙基苯,肉豆蔻酸异丙酯,乳酸,月桂胺,异亚丙基丙酮,甲氧基-丙醇,甲基异戊基酮,甲基异丁基酮,月桂酸甲酯,辛酸甲酯,油酸甲酯,二氯甲烷,间二甲苯,正己烷,正辛胺,十八烷酸,乙酸辛胺,油酸,油胺,邻二甲苯,苯酚,聚乙二醇(PEG400),丙酸,丙二醇,丙二醇单甲醚,对二甲苯,甲苯,磷酸三乙酯,三甘醇,二甲苯磺酸,石蜡,矿物油,三氯乙烯,全氯乙烯,乙酸乙酯,乙酸戊酯,乙酸丁酯,甲醇,乙醇,异丙醇,以及较高分子量的醇如戊醇、四氢糠醇、己醇、辛醇等,乙二醇,丙二醇,甘油和N-甲基-2-吡咯烷酮。水通常是用于稀释浓缩物的所选载体。
适宜的固体载体包括,例如滑石,二氧化钛,叶蜡石粘土,二氧化硅,凹凸棒石粘土,硅藻土(kieselguhr),白垩,硅藻土(diatomaxeousearth),石灰,碳酸钙,膨润土,漂白土,棉籽壳,小麦面粉,大豆面粉,浮石,木屑,胡桃壳粉和木质素。
在所述的液体和固体组合物中,特别是设计为在施用前用载体稀释的那些,有利地采用宽范围的表面活性剂。在使用时,这些试剂通常占配制剂重量的0.1%至15%。它们的特性可以是阴离子、阳离子、非离子或聚合物,并且可以用作乳化剂、润湿剂、助悬剂或者用于其他目的。典型的表面活性剂包括烷基硫酸酯盐,如月桂基硫酸酯二乙醇铵盐;烷基芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚-环氧烷烃加成产物,如壬酚-C.sub.18乙氧基化物;醇-环氧烷烃加成产物,如十三烷基醇-C.sub.16乙氧基化物;皂,如硬脂酸钠;烷基萘磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯盐,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季胺,如月桂基三甲基氯化铵;脂肪酸聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷与环氧丙烷嵌段共聚物;以及单烷基和二烷基磷酸酯盐。
通常用于农业组合物的其它助剂包括结晶抑制剂,粘度调节剂,助悬剂,喷雾滴调节剂,色素,抗氧化剂,起泡剂,消泡剂,遮光剂,增容剂,止泡剂,螯合剂,中和剂和缓冲剂,腐蚀抑制剂,染料,增香剂,展布剂,助渗剂,微量营养素,软化剂,润滑剂和粘着剂。
此外,其它杀生物活性成分或组合物可以与式(I)化合物相组合,并且用于本发明方法中,而且与式(I)化合物同时或按顺序施用。在同时施用的情况下,这些其它活性成分可以与式(I)化合物一起配制或者在例如喷雾槽中混合。这些其它杀生物活性成分可以是杀真菌剂,除草剂,杀昆虫剂,杀细菌剂,杀螨剂,杀线虫剂和/或植物生长调节剂。
相应地,本发明提供组合物,其包含式(I)化合物和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
另外,本发明提供组合物在本发明方法中的用途,所述组合物包含式(I)化合物,和(i)杀真菌剂,(ii)除草剂,(iii)杀昆虫剂,(iv)杀菌剂,(v)杀螨剂,(vi)杀线虫剂和/或(vii)植物生长调节剂。
本发明的化合物和组合还可以用于防治工业材料的真菌侵染(特别是霉菌和白粉菌侵染),包括保护工业材料防范真菌侵袭以及在侵染发生之后减少或根除工业材料的真菌侵染。工业材料包括例如有机和无机材料木材,纸张,皮革,天然和合成纤维,其复合物比如刨花板、胶合板、壁板等,机织和非机织织物,建筑表面和材料,冷却和加热系统表面和材料,通风和空调系统表面和材料,等。根据本发明的化合物和组合可以施用至上述材料或表面,其量可以如上所述以类似方式有效抑制或预防不利效果比如腐蚀、脱色或发霉。使用或包括其中已施用所述化合物或组合的工业材料来建造的建筑或居所也同样受到保护对抗真菌攻击。
相应地,在又一方面,本发明提供防治或预防病原微生物侵染工业材料的方法,包括将式(I)化合物或其组合物以有效防治所述微生物的量施用至所述工业材料、其部分或其处所。
本发明化合物和组合还可以出于医学和兽医学意图用于治疗人类和动物受试者(比如马、牛、绵羊、狗、猫)的真菌侵染。上述感染的实例包括爪真菌病,孢子丝菌病,腐蹄病,丛林溃疡,波伊德伪霉样真菌(Pseudallescheria boydii),帚霉属或运动员脚,某些情况下一般称为″白线”病,以及在免疫受损的患者比如AIDS患者和移植患者中的真菌侵染。从而,真菌侵染可以是皮肤或角质物质比如毛发、蹄或甲的感染,以及全身性感染比如由念珠菌属(Candida spp.),新生隐球菌(Cryptococcusneoformans),和曲霉属(Aspergillus spp.)引起的那些,比如肺曲霉病和卡氏肺囊虫(Pneumocystis carinii)肺炎。本发明化合物和组合可以与药学上可接受的载体相组合,并按照已知技术以有效治疗感染的量给予或施用至上述受试者或感染(例如,局部、经肠胃外)。
相应地,在又一方面,本发明提供在有此需要的受试者中治疗真菌侵染的方法,包括将式(I)化合物或其组合物以有效治疗所述真菌侵染的量给予至所述受试者。
式(I)化合物可以用下述方法制备。
异噁唑,其中R1≠H,可以用标准酰化或氨基甲酰基化条件制备自(I)(R1=H)。例如,(I)的乙酸酯衍生物(R1=COCH3)可以这样合成自醇(I)(R1=H):在室温下于醚溶剂中与乙酸酐和吡啶反应过夜。酰化可以在惰性溶剂(例如乙醚,二氯甲烷)中的有机碱存在下用酸酐(例如乙酸酐、丙酸酐)或酰氯(例如苯甲酰氯)来进行。氨基甲酰基化这样进行:用强碱比如氢化钠处理醇(I),随后用惰性溶剂比如DMF(二甲基甲酰胺)中的氨基甲酰氯(例如N,N-二甲基氨基甲酰氯)进行处理。
实施例1:[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇
(i)制备3-(2,4-二氟苯基)-1-吡啶-3-基-丙炔酮(3)
将1-乙炔基-2,4-二氟苯(24g,0.17mol)溶于THF(350ml),在-78℃冷却反应混合物。在70分钟内滴加2.5M的n-BuLi己烷溶液(76.5ml,0.19mol),保持温度在-70℃以下。在加入完成之后,在该温度将混合物再搅拌10分钟。在20分钟内,将Weinreb酰胺2(根据WO 05/097760,Letters in Organic Chemistry,4,20,2007制备)(28.9g,0.17mol)的THF(100ml)溶液滴加至上述溶液,保持温度在-70℃以下。然后,将混合物温热至-50℃,获得溶液,将其在该温度再搅拌1小时。反应混合物用饱和氯化铵溶液(100ml)淬灭,让其温热至室温。然后,将反应倾至乙酸乙酯/水混合物中。随后,水相用乙酸乙酯洗涤两次。经合并的有机层用盐水洗涤,在硫酸钠上干燥,过滤,浓缩。自乙醚重结晶粗制品,获得28g的希望产品。浓缩母液,残余物通过柱色谱法在氧化铝上纯化,用环己烷/乙酸乙酯3∶1混合物洗脱。共获得,29.8g(70%)的褐色化合物。
1H NMR(CDCl3):δ7.02(m,1),7.58(m,1),7.71(m,1),8.56(m,1)8.90(m,1)和9.48ppm(m,1)。MS m/z:244.0(M+H)。
(ii)制备[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲酮(5)
向121g(697mmol)的2-氟-4-氯甲基苯甲醛肟的500ml二甲基甲酰胺溶液加入93g(697mmol)的N-氯代琥珀酰亚胺(参见K.C.Liu,B.R.Shelton,和R.K.Howe,J.Org.Chem.1980,45,3916)。在室温下搅拌反应混合物2小时,然后用乙酸乙酯稀释。乙酸乙酯溶液用水、饱和氯化钠洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去溶剂,提供130g(90%)的黄色晶状2-氟-4-氯-N-羟基苯亚氨代甲基氯。
于85℃,将46.7g(0.22mol)的2-氟-4-氯-N-羟基苯亚氨代甲基氯,42g(0.17mol)的3-(2,4-二氟苯基)-1-吡啶-3-基-丙炔酮(3),和21.76g(0.26mol)的碳酸氢钠在500mL异丙醇中的混合物加热21小时。反应混合物用乙酸乙酯稀释,依次用饱和氯化铵、水和饱和氯化钠溶液洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙酸乙酯。自乙醚重结晶粗制品,获得所希望的产品,是淡黄色固体(50.28g,70.2%)。
1H NMR(CDCl3):δ6.75(m,1),7.05(m,2),7.27(m,2),7.67(t,1),7.80(m,1),8.03(m,1),8.66(m,1)和8.82ppm(d,1)。MSm/z:415(M+H)。
(iii)制备[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇(6)
于0℃,向5(26.5g,63.9mmol)的THF/甲醇(400ml/40ml)混合物溶液加入2.42g(63.7mmol)的硼氢化钠。搅拌混合物1.5小时,然后用乙酸乙酯稀释。乙酸乙酯溶液用饱和氯化钠溶液洗涤,在硫酸镁上干燥。滤出干燥剂,旋蒸除去乙酸乙酯。反应混合物通过柱色谱法用庚烷/乙酸乙酯1∶1混合物纯化。获得所希望的化合物,是白色晶体(17.5g,66%)。mp=138-140℃。
1H NMR(CDCl3):δ4.19(bs,1),5.89(s,1),6.99(m,5),7.28(t,1),7.43(d,1),7.59(q,1),和8.19(d,1)和8.23ppm(d,1)。MS m/z:417(M+H)。
实施例2:(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇
用外消旋混合物6作原料,通过制备型色谱法分离各对映体。
制备方法:
流动相:正庚烷/乙醇70/30(v/v)
流速:270ml/分
检测:UV 280nm
温度:25℃
分析方法:
流动相:正庚烷/乙醇/二乙胺70/30/0.1(v/v/v)
流速:1ml/分
检测:UV 230nm
温度:25℃
第一洗脱对映体具有的保留时间为7.6分钟([α]=+58.07,C=0.025M,THF),而第二对映体具有的保留时间为9.9分钟([α]=-57.59,C=0.025M,THF)。第二洗脱对映体是(S)-对映体。
生物学实施例:实施例2的杀真菌特性展示于下述实施例中。
灰葡萄孢(Botryti)cinerea)(灰霉病):将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法测定生长抑制。实施例2于200ppm提供至少80%的灰葡萄孢防治。
落花生球腔菌(Mycosphaerella arachidis)(同义词:落花生尾孢(Cercospora arachidicola)),落花生(花生)褐斑病:将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法于620nm测定生长抑制。实施例2于200ppm提供至少80%的落花生球腔菌防治。
小麦壳针孢(Septoria tritici)(叶枯病):将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法测定生长抑制。实施例2于200ppm提供至少80%的小麦壳针孢防治。
雪腐明梭孢(Monographella nivalis)(同义词:雪腐微托菌(Microdochium nivale),雪腐镰孢(Fusarium nivale)),禾谷类的雪腐病、根腐病:将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,72小时之后通过光度法于620nm测定生长抑制。实施例2于200ppm提供至少80%的雪腐明梭孢防治。
大刀镰孢(Fusarium culmorum)(根腐病):将来自低温存储器的真菌的分生孢子直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌孢子的营养肉汤。在24℃温育试验板,48小时之后通过光度法测定生长抑制。实施例2于200ppm提供至少80%的大刀镰孢防治。
立枯丝核菌(Rhizoctonia solani)(根腐病,猝倒病):将制备自新鲜液体培养物的上述真菌的菌丝体碎片直接混合至营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的(DMSO)溶液置于微滴定板(96-孔规格)中后,加入含有真菌菌丝体的营养肉汤。在24℃温育试验板,48小时之后通过光度法测定生长抑制。实施例2于200ppm提供至少80%的立枯丝核菌防治。
Claims (13)
2.根据权利要求1的化合物,其中R1是H。
3.根据权利要求1或权利要求2的化合物,其是式(I)化合物的(S)-对映体。
4.根据权利要求3的化合物,其是(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异噁唑-4-基]吡啶-3-基-甲醇
5.根据权利要求3或权利要求4的化合物,具有至少80%的(S)对(R)的对映体过量。
6.一种组合物,其包含根据权利要求1至5中任一项的化合物,或其农业化学上可接受的盐,和农业化学上可接受的稀释剂或载体。
7.根据权利要求6的组合物,其还包含至少一种其它杀真菌剂或系统获得性抗性诱导物。
8.根据权利要求1至5中任一项的化合物或根据权利要求6或权利要求7的组合物作为杀真菌剂的用途。
9.防治或预防病原微生物侵染栽培植物、植物繁殖材料或工业材料的方法,包括将根据权利要求1至5中任一项的化合物或根据权利要求6或权利要求7的组合物以有效防治所述微生物的量施用至所述植物、其部分或其处所、植物繁殖材料或者工业材料。
10.根据权利要求9的方法,其中所述植物繁殖材料包括种子。
11.根据或权利要求10的方法,其中所述病原微生物是真菌有机体。
12.根据权利要求11的方法,其中所述真菌有机体选自小麦壳针孢(Septoria tritici),颖枯壳多孢(Stagonospora nodorum),致病疫霉(Phytophthora infestans),灰葡萄孢(Botrytis cinerea),同果核盘菌(Sclerotinia homoeocarpa)和隐匿柄锈菌(Puccinia recondite)。
13.在有此需要的受试者中治疗真菌侵染的方法,包括将根据权利要求1至5中任一项的化合物或其药学上可接受的盐以有效治疗所述真菌侵染的量给予至所述受试者。
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