# US 5,344,958 A · Insecticidal N'-substituted-N,N'-diacylhydrazines

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- Number: US 5,344,958 A
- Document ID: US5344958A
- Status: Granted
- Kind: A
- Application number: 07/984,189
- Filed: 1992-11-23
- Granted: 1994-09-06
- Earliest claimed: 1992-11-23
- Assignees: Rohm and Haas Company
- Inventors: Zev Lidert; Dat P. Le
- Web page: https://patentgrep.com/patent/US5344958A

## CPC

- C07D 213/54: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A01N 37/40: having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
- A01N 43/30: with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
- A01N 43/32: six-membered rings
- C07C 243/38: with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C07C 251/86: having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
- C07C 255/24: containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C07C 275/28: having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C 311/51: Y being a hydrogen or a carbon atom
- C07C 323/48: to nitrogen atoms
- C07C 327/56: having nitrogen atoms of thiocarboxamide groups further bound to another hetero atom
- C07D 207/34: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 213/87: in position 3
- C07D 241/24: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 303/38: with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 307/58: One oxygen atom, e.g. butenolide
- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 317/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 319/18: Ethylenedioxybenzenes, not substituted on the hetero ring
- C07D 333/38: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07C 2601/04: with a four-membered ring
- C07C 2601/14: The ring being saturated
- C07C 2601/16: the ring being unsaturated
- C07C 2602/10: the other ring being six-membered, e.g. tetraline
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Insecticidal compounds having the formula N-(2-R.sup.a -3-R.sup.b -benzoyl)-N'-(2-R.sup.c -3-R.sup.d -4-R.sup.e -5-R.sup.f -benzoyl)-N'-R.sup.g -hydrazine, where R.sup.a is a halogen or a lower alkyl; R.sup.b is lower alkoxy; R.sup.c-f are selected from hydrogen, bromo, chloro, fluoro, lower alkyl and lower alkoxy; and Rg is a (C.sub.4 -C.sub.6)alkyl or (C.sub.4 -C.sub.6)alkenyl; as well as compositions comprising an agronomically acceptable carrier and an insecticidally effective amount of such compounds; and methods of using such compounds and compositions. Also, methods for the production of the compounds and their intermediates, which methods comprise admixing a 3-amino-2-(substituted)-benzoic acid, sodium nitrite and methanol under acidic conditions.

## Claims

### Claim 1

A process for producing 3-methoxy-2-(substituted)-benzoic acid or ester of 3-methoxy-2-(substituted)-benzoic acid comprising admixing at a temperature of from about 25 degrees Centigrade to about 75 degrees Centigrade
(a) a con, position comprising
(i) a 3-amino-2-(substituted)-benzoic acid or its respective ester and
(ii) methanol or a mixture of methanol and water under acidic conditions; and
(b) an effective amount of an inorganic acid; and
(c) sodium nitrite.

### Claim 2 (depends on 1)

The process of claim 1 wherein the inorganic acid is selected from hydrobromic acid, hydrochloric acid, phosphoric acid, and sulfuric acid.