1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters, and ethers,
composition containing them, and use of them to control phytopathogenic
microorganisms
    1.
    发明授权
    1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters, and ethers, composition containing them, and use of them to control phytopathogenic microorganisms 失效
    1-芳基-2-氟-2-噻唑烷酮,链烷醇,酯和醚,含有它们的组合物,以及它们用于控制植物病原微生物

    公开(公告)号:US4690942A

    公开(公告)日:1987-09-01

    申请号:US681989

    申请日:1984-12-14

    Abstract: The invention relates to 1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters and ethers of formula I ##STR1## wherein Az is 1H-1,2,4-triazole, 4H-1,2,4-triazole or 1H-imidazole;T is --C(O)--, --CH(OH)-- or one of the groups ##STR2## wherein R.sub.7 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.3 -alkoxy, halogen or cyano, or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, 2-furyl, 2-tetrahydrofuryl, or is phenyl or benzyl, each unsubstituted or substituted by halogen, nitro, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkyl and/or C.sub.1 -C.sub.3 haloalkoxy;R.sub.8, R.sub.9 and R.sub.10 are each independently hydrogen, nitro, halogen, cyano, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, --COO(C.sub.1 -C.sub.3 alkyl), NH.sub.2 or NHCOCH.sub.3 ;R is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.1 and R.sub.2 are each independently hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, nitro and/or cyano; andR.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, nitro, cyano and/or the group ##STR3## wherein X is O, S, SO or SO.sub.2 ;R.sub.4, R.sub.5 and R.sub.6 are each independently hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl and/or C.sub.1 -C.sub.6 haloalkoxy; and to the acid addition salts and metal complexes thereof.These compounds have microbicidal properties and can be used in particular against diseases occurring in rice.The invention also relates to the preparation and use of these compounds.

    Abstract translation: 本发明涉及式I的1-芳基-2-氟-2-噻唑烷酮,链烷醇,酯和醚其中Az是1H-1,2,4-三唑,4H-1,2, 4-三唑或1H-咪唑; T是-C(O) - , - CH(OH) - 或其中一个基团,其中R 7是未被取代或被C 1 -C 3 - 烷氧基,卤素或氰基取代的C 1 -C 6烷基,或者是C 3 -C 6烯基 硝基,C 1 -C 3烷基,C 1 -C 3烷氧基,C 1 -C 3卤代烷基和/或C 1 -C 3烷氧基,C 3 -C 6炔基,C 3 -C 6环烷基,2-呋喃基,2-四氢呋喃基,或者是苯基或苄基, C3卤代烷氧基; R8,R9和R10各自独立地为氢,硝基,卤素,氰基,C1-C3烷基,C1-C3烷氧基,C1-C3卤代烷氧基,-COO(C1-C3烷基),NH2或NHCOCH3; R是氢或C 1 -C 6烷基; R 1和R 2各自独立地为氢,卤素,C 1 -C 6烷基,C 1 -C 6 - 烷氧基,C 1 -C 6卤代烷基,C 1 -C 6卤代烷氧基,硝基和/或氰基; 并且R 3是氢,卤素,C 1 -C 6烷基,C 1 -C 6烷氧基,C 1 -C 6卤代烷基,C 1 -C 6卤代烷氧基,硝基,氰基和/或其中X是O,S,SO或SO 2; R4,R5和R6各自独立地为氢,卤素,氰基,硝基,C1-C6烷基,C1-C6烷氧基,C1-C6卤代烷基和/或C1-C6卤代烷氧基; 和其酸加成盐和金属络合物。 这些化合物具有杀微生物的性质,特别可用于防治水稻中发生的疾病。 本发明还涉及这些化合物的制备和用途。

    3-Phenyl-4-cyanopyrrole derivatives, the preparation thereof, and method
of use thereof as microbicides
    2.
    发明授权
    3-Phenyl-4-cyanopyrrole derivatives, the preparation thereof, and method of use thereof as microbicides 失效
    3-苯基-4-氰基吡咯衍生物,其制备方法及其作为杀微生物剂的使用方法

    公开(公告)号:US4567052A

    公开(公告)日:1986-01-28

    申请号:US618867

    申请日:1984-06-08

    Applicant: Robert Nyfeler

    Inventor: Robert Nyfeler

    CPC classification number: C07D405/12 A23L3/3526 A23L3/3544 C07D207/34

    Abstract: The invention relates to novel N-alkylated 3-phenyl-4-cyanopyrrole derivatives of the formula I ##STR1## wherein R.sub.1 and R.sub.2, each independently of the other, are hydrogen, halogen, methoxy or methylthio,R.sub.3 is hydrogen or C.sub.1 -C.sub.8 haloalkyl,Y is hydroxy, halogen or the --O--C(O)--R.sub.4 group, andR.sub.4 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.2 -C.sub.6 alkenyl, 2-tetrahydrofuryl, 2-tetrahydropyranyl, C.sub.1 -C.sub.6 alkoxycarbonyl or the --CH(R.sub.5)--XR.sub.6 group, whereinX is oxygen or sulfur,R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl, andR.sub.6 is C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkoxy)-C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, phenyl or phenyl which is substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, or C.sub.1 -C.sub.6 alkoxycarbonyl.The invention also relates to the preparation of these compounds by N-alkylation of the starting pyrroles, as well as to microbicidal compositions which contain a compound of formula I as active ingredient. Also disclosed is a method of controlling phytopathogenic micro-organisms which comprises the use of the novel compounds.

    Abstract translation: 本发明涉及式I(I)的新型N-烷基化3-苯基-4-氰基吡咯衍生物,其中R 1和R 2各自独立地为氢,卤素,甲氧基或甲硫基,R 3为氢或 C1-C8卤代烷基,Y是羟基,卤素或-OC(O)-R4基团,R4是氢,C1-C8烷基,C1-C8卤代烷基,C2-C6链烯基,2-四氢呋喃基,2-四氢吡喃基,C1-C6烷氧基羰基或 -CH(R5)-XR6基,其中X是氧或硫,R5是氢或C1-C3烷基,R6是C1-C6烷基,(C1-C6烷氧基)-C1-C6烷基,C3-C6链烯基,C3-C6炔基,苯基 或被卤素,C 1 -C 6烷基,C 1 -C 6烷氧基或C 1 -C 6烷氧基羰基取代的苯基。 本发明还涉及通过起始吡咯的N-烷基化制备这些化合物,以及含有式I化合物作为活性成分的杀微生物剂组合物。 还公开了一种控制植物病原微生物的方法,其包括使用该新化合物。

    Process and a composition for immunizing plants against diseases
    3.
    发明授权
    Process and a composition for immunizing plants against diseases 失效
    用于免疫植物以防止疾病的方法和组合物

    公开(公告)号:US5190928A

    公开(公告)日:1993-03-02

    申请号:US683582

    申请日:1991-04-10

    Abstract: A method and composition for the immunization of healthy useful plants against plant diseases containing as active ingredients compounds of formula ##STR1## in which: X is hydrogen, halogen, hydroxy, methyl, methoxy, HOOC or MOOC;Y is hydrogen, halogen, SO.sub.3 H, SO.sub.3 M, nitro, hydroxy or amino, M being the molar equivalent of an alkali metal or alkaline earth metal ion that is formed from a corresponding base or basic compound; andZ is cyano or --CO--A;A represents either --OH or --SH, the hydrogen atom of which may also be replaced by the molar equivalent of an inorganic or organic cationic residue,or wherein A represents any other organic residue which has a molecular weight of less than 900 and which may also contain one, or more than one, hetero atom, including the salts of the phytophysiologically tolerable 7-carboxylic acid or 7-thiocarboxylic acid with primary, secondary or tertiary amines or with inorganic bases.

    Abstract translation: 含有作为活性成分的式(I)化合物的健康有益植物免疫植物病害的方法和组合物,其中:X是氢,卤素,羟基,甲基,甲氧基,HOOC或MOOC; Y是氢,卤素,SO 3 H,SO 3 M,硝基,羟基或氨基,M是由相应的碱或碱化合物形成的碱金属或碱土金属离子的摩尔当量; 和Z是氰基或-CO-A; A表示-OH或-SH,其氢原子也可被无机或有机阳离子残基的摩尔当量代替,或其中A表示分子量小于900的任何其它有机残基, 还含有一个或多于一个杂原子,包括植物生理学上可耐受的7-羧酸或7-硫代羧酸与伯胺,仲胺或叔胺或与无机碱的盐。

    Agents for protecting plants against diseases
    4.
    发明授权
    Agents for protecting plants against diseases 失效
    保护植物抗病的药剂

    公开(公告)号:US5066661A

    公开(公告)日:1991-11-19

    申请号:US489414

    申请日:1990-03-06

    CPC classification number: C07D285/14 A01N43/82 C07D417/12

    Abstract: The invention relates to novel N-(cyanomethyl)-benzo-1,2,3-thiadiazole-7-carboxamides of the formula I ##STR1## in which X.sub.1 and X.sub.2 independently of one another are hydrogen or 1 to 3 halogen; R is hydrogen C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.5 alkenyl or SR.sub.1 ; R.sub.1 is C.sub.1 -C.sub.3 alkyl which is substituted by 3 to 6 fluorine or chlorine; R.sub.2 is C.sub.1 -C.sub.4 alkyl, or is C.sub.1 -C.sub.5 alkyl which is interrupted by oxygen, or is C.sub.1 -C.sub.6 alkoxy, or is C.sub.1 -C.sub.3 alkyl which is substituted by 1 to 3 halogen, or is substituted C.sub.2 -C.sub.3 alkoxy, or is C.sub.1 -C.sub.6 alkylthio, or is furyl or thienyl, each of which is bonded in the 2- or 3-position, or is furyl or thienyl, each of which is substituted by 1 to 3 halogen and bonded in the 2- or 3-position; and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl.Such compounds, by themselves or in the form of formulated agents, can be used for protecting plants against harmful microorganisms.

    Abstract translation: 本发明涉及式I(I)的新的N-(氰基甲基) - 苯并-1,2,3-噻二唑-7-甲酰胺,其中X 1和X 2彼此独立地是氢或1至3个卤素 ; R是氢C1-C4烷基,C3-C5链烯基或SR1; R1是被3-6个氟或氯取代的C1-C3烷基; R2是C1-C4烷基,或是被氧中断的C1-C5烷基,或是C1-C6烷氧基,或是被1至3个卤素取代的C1-C3烷基或被取代的C2-C3烷氧基或C1-C6烷硫基取代的C1-C3烷基, 或者是呋喃基或噻吩基,它们各自键合在2-或3-位,或是呋喃基或噻吩基,其各自被1至3个卤素取代并键合在2-或3-位; 并且R 3是氢或C 1 -C 4烷基。 这些化合物本身或配制剂的形式可用于保护植物免受有害微生物的侵害。

    Difluorbenzodioxyl cyanopyrrole microbicidal compositions
    5.
    发明授权
    Difluorbenzodioxyl cyanopyrrole microbicidal compositions 失效
    二氟苯并二氧环戊基氰基吡咯杀微生物剂

    公开(公告)号:US4705800A

    公开(公告)日:1987-11-10

    申请号:US874193

    申请日:1986-06-13

    CPC classification number: C07D317/60 C07D405/04 C07D405/14

    Abstract: The invention relates to novel 3-phenyl-4-cyanopyrrole derivatives of the general formula ##STR1## wherein X has the following meaning: A: hydrogen or CO--R.sub.1, wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkylnyl, or C.sub.1 -C.sub.6 alkoxy which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 14 C.sub.6 alkenyloxy, or C.sub.3 -C.sub.6 cycloalkyl;B: S--R.sub.2, wherein R.sub.2 is C.sub.1 -C.sub.3 haloalkyl;C: CH(Y)R.sub.3, wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.8 haloalklyl and Y is hydroxy, halogen or OC(O)R.sub.4, wherein R.sub.4 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.1 -C.sub.6 alkoxycarbonyl; orD: CH.sub.2 --Z, wherein Z is the group ##STR2## in which formula each of R.sub.5 and R.sub.6 independently of the other is hydrogen, C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by cyano or C.sub.1 -C.sub.6 alkoxycarbonyl; or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, or phenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl or C.sub.1 -C.sub.6 alkoxy, with the proviso that only R.sub.5 or R.sub.6 may be hydrogen.

    Abstract translation: 本发明涉及通式为“IMAGE”的新型3-苯基-4-氰基吡咯衍生物,其中X具有以下含义:A:氢或CO-R 1,其中R 1是未被取代或被卤素或C 1取代的C 1 -C 6烷基 -C3烷氧基; 或是未被取代或被卤素或C 1 -C 3烷氧基取代的C 3 -C 6烯基,C 3 -C 6烷基或C 1 -C 6烷氧基; 或为C 3-14 C 6链烯氧基或C 3 -C 6环烷基; B:S-R2,其中R2是C1-C3卤代烷基; C:CH(Y)R 3,其中R 3是氢或C 1 -C 8卤代烷基,Y是羟基,卤素或OC(O)R 4,其中R 4是C 1 -C 8烷基,C 1 -C 8卤代烷基,C 2 -C 6烯基或C 1 -C 6烷氧基羰基; 或D:CH 2 -Z,其中Z为基团,其中R 5和R 6各自独立地为氢,未被取代或被氰基或C 1 -C 6烷氧基羰基取代的C 1 -C 6烷基; 或者是未被取代或被卤素,C 1 -C 6烷基,C 1 -C 6卤代烷基或C 1 -C 6烷氧基取代的C 3 -C 6烯基,C 3 -C 6炔基,C 3 -C 7环烷基或苯基,条件是仅R5或R6可以是氢。

    Fungicidal 3-(N-carbonylamino)-pyrrolidine-2,5-diones
    7.
    发明授权
    Fungicidal 3-(N-carbonylamino)-pyrrolidine-2,5-diones 失效
    杀真菌剂3-(N-羰基氨基) - 吡咯烷-2,5-二酮

    公开(公告)号:US4332816A

    公开(公告)日:1982-06-01

    申请号:US212471

    申请日:1980-12-03

    Applicant: Robert Nyfeler

    Inventor: Robert Nyfeler

    Abstract: Novel compounds of the formula ##STR1## wherein R.sub.1 is chlorine, bromine or nitro, R.sub.2 is chlorine or bromine, R.sub.3 is hydrogen or fluorine, R.sub.4 is C.sub.1 -C.sub.9 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, or is C.sub.2 -C.sub.7 alkenyl, C.sub.2 -C.sub.4 alkynyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is unsubstituted or substituted by halogen or aryl, or is phenyl which is unsubstituted or substituted by halogen, nitro or C.sub.1 -C.sub.4 alkyl, or is a 5-membered heterocyclic ring system which contains a hetero-atom, or is X-R.sub.5, wherein X is oxygen or sulfur and R.sub.5 is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl, each of which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, or is phenyl which is unsubstituted or substituted by halogen, nitro, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, or is benzyl which is unsubstituted or substituted by halogen or nitro.These compounds possess useful microbicidal properties and can be used for controlling phytopathogenic microorganisms, especially phytopathogenic fungi. They have, for practical purposes, a very advantageous curative, preventive and systemic action for protecting cultivated plants, without adversely affecting these by undesirable side-effects.

    Abstract translation: 新的式(Ⅰa)化合物,其中R1是氯,溴或硝基,R2是氯或溴,R3是氢或氟,R4是未被取代或被卤素或C1-C3烷氧基取代的C 1 -C 9烷基, C 7链烯基,C 2 -C 4炔基或C 3 -C 6环烷基,其各自为未取代的或被卤素或芳基取代,或者是未被取代或被卤素,硝基或C 1 -C 4烷基取代的苯基,或是含有 或是X-R5,其中X是氧或硫,R5是C1-C6烷基或C3-C6烯基,它们各自是未取代的或被卤素或C1-C3烷氧基取代,或是未取代或取代的苯基 卤素,硝基,C 1 -C 3烷基或C 1 -C 3烷氧基,或者是未被取代或被卤素或硝基取代的苄基。 这些化合物具有有用的杀菌特性,可用于控制植物病原微生物,特别是植物病原真菌。 为了实际目的,它们具有非常有利的治疗,预防和全身作用,用于保护栽培植物,而不会由不良副作用影响。

    Microbicidal compositions
    9.
    发明授权
    Microbicidal compositions 失效
    杀菌组合物

    公开(公告)号:US5250557A

    公开(公告)日:1993-10-05

    申请号:US792845

    申请日:1991-11-15

    CPC classification number: A01N43/653

    Abstract: The combination of the plant microbicide 4-(2,2-difluoro-1,3-benzodioxol-7-yl)-1H-pyrrole-3-carbonitrile with the plant microbicide 1-{2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-ylmethyl}-1H-1,2,4-triazole results in a synergistically increased effect in the control of plant diseases. Microbicidal compositions based on such combinations are suitable for treating crops of plants and natural products of vegetable and animal origin, and for seed treatment.

    Abstract translation: 植物杀菌剂4-(2,2-二氟-1,3-苯并间二氧杂环戊烯-7-基)-1H-吡咯-3-腈与植物杀菌剂1- {2- [2-氯-4-( 4-氯苯氧基)苯基] -4-甲基-1,3-二氧戊环-2-基甲基} -1H-1,2,4-三唑导致在控制植物疾病中协同增加的效果。 基于这种组合的杀微生物组合物适用于处理植物和植物和动物来源的天然产物的作物以及种子处理。

    Difluorobenzodioxyl cyanopyrrole microbicidal compositions
    10.
    发明授权
    Difluorobenzodioxyl cyanopyrrole microbicidal compositions 失效
    二氟苯二甲基氰基吡咯杀微生物组合物

    公开(公告)号:US4925840A

    公开(公告)日:1990-05-15

    申请号:US228763

    申请日:1988-08-03

    CPC classification number: C07D317/60 C07D405/04 C07D405/14

    Abstract: The invention relates to novel 3-phenyl-4-cyanopyrrole derivatives of the general formula ##STR1## wherein X has the following meanings:A: hydrogen or CO--R.sub.1, wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, or C.sub.1 -C.sub.6 alkoxy which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy; or is C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 cycloalkyl, or tetrahydrofur-2-yl;B: S--R.sub.2, wherein R.sub.2 is C.sub.1 -C.sub.3 haloalkyl;C: CH(Y)R.sub.3, wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.8 haloalkyl and Y is hydroxy, halogen or OC(O)R.sub.4, wherein R.sub.4 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.1 -C.sub.6 alkoxycarbonyl; orD: CH.sub.2 --Z, wherein Z is the group ##STR2## wherein each of R.sub.7 and R.sub.8 independently of the other is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxycarbonyl, or both together form a fused aromatic ring; each of R.sub.9 and R.sub.10 independently of the other is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxycarbonyl; and X is oxygen, sulfur, ##STR3## wherein R.sub.11 is hydrogen, C.sub.1 -C.sub.6 alkyl, formyl, C.sub.1 -C.sub.6 alkanol or C.sub.1 -C.sub.6 alkoxycarbonyl; and n is 0 or 1.The novel compounds are used for controlling harmful microorganisms, in particular phytopathogenic fungi. They can be employed together with suitable formulation adjuvants as compositions and are also suitable for protecting cultivated plants from attack by harmful microorganisms.

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