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Usage

Uses

Used in Agricultural Industry:
9-(DichloroMethylene)-1,2,3,4-tetrahydro-1,4-Methanonaphthalen-5-aMine is used as a fungicide in fungicidal compositions for controlling rust diseases of soybean plants. Its effectiveness in combating these diseases helps protect crops and improve overall yield, making it a valuable component in agricultural practices aimed at maintaining plant health and productivity.

Upstream product

• 1345203-43-1 5-bromo-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene 
• 1345202-89-2 [2,3]epoxy-5-nitro-1,2,3,4-tetrahydro-1,4-methanonaphthalene 
• 1345202-91-6 5-amino-1,2,3,4-tetrahydro-1,4-methanonaphthalene-9-ol 
• 50573-74-5 6-nitroanthranilic acid 
• 542-92-7 cyclopenta-1,3-diene 
• 58673-43-1 1,4-dihydro-5-nitro-1,4-methanonaphthalene 

Relevant academic research and scientific papers

2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol and preparation method thereof

The invention provides a chemical compound which can serve as an intermediate for benzovindiflupyr synthesis. The chemical compound is 2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol with the chemical formula as shown in formula (IV) in the specification. The invention further provides a method for preparing the chemical compound, 2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol. The method comprises: a chemical compound, [2,3]-epoxy-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene, as shown in formula (III) reacts in a hydrobromic acid aqueous solution at 20 DEG C, and the chemical compound as shown in formula (IV) is prepared. The invention finds a novel method for producing a key intermediate for benzovindiflupyr and a preparation method thereof, thereby enabling the route for benzovindiflupyr synthesis to be more reasonable.

Intermediate of benzovindiflupyr and preparation method and application thereof

The invention provides an intermediate of benzovindiflupyr and a preparation method and application thereof. The compound is N-(1,2,3,4-tetrahydro-1,4- methanonaphthalene-naphthalene-9-phenol-5-yl-)- phthalimide, and the chemical formula (VI) is defined in the following description. According to the preparation method, the compound, namely 5-amino-1,2,3,4-tetrahydro-1,4-methanonaphthalene-naphthalene-9-phenol and phthalic anhydride react under a high-temperature molten state, then an organic solvent is added, and the compound in the formula (VI) is prepared. The preparation method is easy and convenient to operate, easy to implement, mild in reaction condition, good in product quality and suitable for large-scale industrialized production.

PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID AMIDES

The invention relates to a process for the preparation of a compound of formula (I), which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species to (III) reacting the halobenzyne of formula (III) so formed with (IV) wherein R1 and R2 are hydrogen or C1-C6alkyl; to (V), b) hydrogenating V in the presence of a metal catalyst to (VI), c) ozonising (VI) to (VII) d) converting (VII) in the presence of a phosphane and CCI4 or CHCI3 to (VIII) (VIII), and either e1 ) reacting VIII with NH3 in the presence of a catalyst to (IX) and f) reacting IX in the presence of a base with the compound of formula (X), to the compound of formula (I); or e2) reacting the compound of formula (VIII), in the presence of a solvent, a base, a copper catalyst and at least one ligand with (Xa), to the compound of formula (I).

PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID AMIDES

The invention relates to a process for the preparation of formula (I) which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species to (III), wherein X is chloro or bromo; reacting the halobenzyne with a fulvene (IV), to a compound of formula(V) wherein X is chloro or bromo; b) hydrogenating V in the presence of a suitable metal catalyst to a compound of formula (VI) wherein X is chloro or bromo; and either c1) reacting the compound of formula VI with NH3 in the presence of a catalyst comprising palladium and at least one ligand to the compound of formula (VII); and d) reacting the compound of formula VII in the presence of a base with a compound of formula (VIII), to the compound of formula I; or c2 reacting the compound of formula (VI) in the presence of a copper catalyst and a ligand with the compound of formula (VIIIa), to the compound of formula (I).

PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID AMIDES

The invention relates to a process for the preparation of the compound of formula (I), which process comprises a) reacting a compound of formula (II), wherein X is chloro or bromo, with an organometallic species in an inert atmosphere to a halobenzyne of formula (X), reacting the halobenzyne of formula X so formed with cyclopentadiene to (III), b) reacting III in the presence of an inert solvent with an oxidant to (IV), c) reacing IV in the presence of a Lewis acid and a hydride source to (V), d) reacting V in the presence of an oxidizing agent, a base and an inert solvent to (VI), e) converting VI in the presence of a phosphane and CCl4 or CHCl3 to (VII), and either f1) reacting VII with NH3 in the presence of a catalyst to the compound of formula (VIII); and g) reacting VIII in the presence of a base with a compound of formula (IX), to the compound of formula (I); or f2) reacting the compound of formula (VII), in the presence of a solvent, a base, a copper catalyst and at least one ligand with the compound of formula (IXa), to the compound of formula (I).

PROCESS FOR THE PREPARATION OF BENZONORBORNENES

The present invention relates to a novel a process for the preparation of 9- dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine which process comprises a) reacting cyclopentadiene in the presence of a radical initiator and CXCI3, wherein X is chloro or bromo, to a compound of formula Il, or aa) reacting cyclopentadiene with CXCI3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula Il, wherein X is chloro, b) reacting the compound of formula Il with a base in the presence of an appropriate solvent to the compound of formula III, c) and converting the compound of formula III in the presence of 1,2-dehydro-6- nitrobenzene to the compound of formula IV, and d) hydrogenating the compound of formula IV in the presence of a metal catalyst.

HETEROCYCLIC AMIDE DERIVATIVES USEFUL AS MICROBIOCIDES

The invention relates to a fungicidally active compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by the groups R6, R7 and R8; R1 is hydrogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, CH2C≡CR9, CH2CR10=CHR11, CH=C=CH2 or COR12; R2 and R3 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl or C1-4 haloalkoxy; R4 and R5 are each independently selected from halo, cyano and nitro; or one of R4 and R5 is hydrogen and the other is selected from halo, cyano and nitro; R6, R7 and R8 are each, independently, hydrogen, halo, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl, C1-4 haloalkoxy(C1-4)alkyl or C1-4 haloalkoxy, provided that at least one of R6, R7 and R8 is not hydrogen; R9, R10 and R11 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkyl; and R12 is hydrogen, C1-6 alkyl, C1-6 haloalkyl, C1-4 alkoxy(C1-4 )alkyl, C1-4 alkylthio(C1-4)- alkyl, C1-4 alkoxy or aryl; to the preparation of these compounds, to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient, to the preparation of the compositions mentioned and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.