928783-29-3

Usage

Uses

Used in Pesticide Industry:
Methanimidamide, N-[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylbenzoyl]-N'-methoxyis used as an insecticide for controlling various insect pests in agriculture. It is a potent inhibitor of γ-aminobutyric acid (GABA)-, glutamate-, and glycine-gated chloride channels in insects, making it effective in managing pest populations and protecting crops. Its unique mode of action also reduces the likelihood of cross-resistance with other insecticides, providing an effective alternative for integrated pest management strategies.

Synthesis

The synthesis route of fluxametamide is shown in Fig. 1. As mentioned earlier, the isoxazoline 9 can be cyclized by reacting the olefin 5 and the chloroaldoxime 8 that are derived from the boronic acid 4 and the aldehyde 6, respectively. CO insertion of 9, followed by the addition of ammonia to carboxylic acid chloride, affords carbamoyl 11.After dimethylamino methylation with N,N-dimethylformamide dimethyl acetal, the dimethylamino group can be converted into the methoxyimino group by using methox- yamine hydrochloride.The asymmetric center of the isoxazoline ring has an insecticidal activity in its S-form, but fluxametamide was developed as a racemate.

in vitro

Fluxametamide is an antagonist of GABA- and glutamate-gated chloride channels, dose-dependently inhibits currents induced by GABA and glutamate in M. domestica GABACls and GluCls, with IC50 values of 1.95 (1.18-3.21) nM and 225 (137-372) nM, respectively, and displays potent antagonistic activity against T. urticae GABACls with an IC50 of 0.219 (0.127-0.381) nM. Fluxametamide inhibits GABA responses in the wild-type L. striatellus GABACls with IC50 values of 1.40 (0.57-3.29) nM; in the A2′N mutant GABACls, the IC50 value is 3.51 (2.17-5.69) nM. Moreover, Fluxametamide scarcely inhibits GABA (EC50)-induced currents in rat GABACls at 10 μM and with no inhibition on glycine (EC50)-induced current in human α1 GlyCls at tested concentrations.

Upstream product

• 864730-52-9 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide 
• 593-56-6 N-methoxylamine hydrochloride 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 928787-48-8 methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]-N-(methoxyiminomethyl)carbamate 
• 928783-31-7 methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]-N-(methoxyiminomethyl)carbamate 

Relevant academic research and scientific papers

ISOXAZOLINE-SUBSTITUTED BENZAMIDE COMPOUND AND PEST CONTROL AGENT

PROBLEM TO BE SOLVED: To provide a novel pest control agent, especially pesticide or acaricide. SOLUTION: There is provided an isoxazoline-substituted benzamide compound represented by the following formula. X, Y represent a halogen atom or the like, R1 represents -CH=NOR1a, R1a represents a C1 to C6 alkyl group or the like, R3 represents a C1 to C6 haloalkyl group, m represents an integer of 1 to 3, and n represents an integer of 0 or 1. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

ISOXAZOLINE SUBSTITUTED BENZAMIDE COMPOUND CRYSTALLINE POLYMORPH-CONTAINING SUSPENSION TYPE COMPOSITION

PROBLEM TO BE SOLVED: To provide a suspension type composition with good storage stability containing (Z)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-(methoxy-imino-methyl)-2-methylbenzoic acid amide. SOLUTION: Provided is a suspension type composition containing a (Z)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-(methoxy-imino-methyl)-2-methylbenzoic acid amide crystal and a dispersion medium in which among the crystals, the content of an I-form crystal which is a crystal form having peaks at diffraction angles 2θ=(7.45±0.2, 11.05±0.2, 12.79±0.2, 15.30±0.2, 20.90±0.2, 21.89±0.2 and 24.32±0.2) in a powder X-ray diffraction by a Cu-Kα ray is 50 to 100 wt.%. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT

INSECTICIDAL, MITICIDAL, NEMATICIDAL, MOLLUSCICIDAL, MICROBICIDAL, OR BACTERICIDAL COMPOSITION AND METHOD FOR CONTROLLING PEST

The present invention provides a novel insecticidal, miticidal, nematicidal, microbicidal, or bactericidal composition and a novel pest control method. An insecticide, miticide, nematicide, molluscicide, disinfectant, or bactericide composition containing

ISOXAZOLINE-SUBSTITUTED BENZAMIDE COMPOUND AND HARMFUL ORGANISM-CONTROLLING AGENT

An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof: wherein A1, A2and A3 independently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., W is oxygen atom or sulfur atom, etc., X is halogen atom, C1-C6haloalkyl, etc., Y ia halogen atm, C1-C6alkyl, etc., R1 is -CH=NOR1a, -C(O)OR1c, -C(O)NHR1d, phenyl substituted with (Z)p1, D-14, D-52, D-53, D-55 to D-59, etc., R1a is C1-C6alkyl, etc., R1c is C1-C6alkyl, etc., R1d is hydrogen atom, -C(O)R15, -C(O)OR15, etc., R2 is C1-C6alkyl, -CH2R14a, C1-C6alkynyl, -C(O)R15, -C(O)OR15, etc., further when R1 is -CH=NOR1a, -C(O)OR1c or -C(O)N(R1e)R1d, R2 may be hydrogen atom, R3 is C1-C6haloalkyl, etc., R14a is cyano, -OR25, etc., R15 is C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl, etc., R25 is C1-C4alkyl, C1-C4haloalkyl, -C(O)R32 or -C(O)OR32, etc., R32 is C1-C6alkyl or C3-C6cycloalkyl, etc., Z is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, etc., m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an interger of 1 to 5. The pesticide containing these compounds.