# US 4,400,512 A · Azaspiro compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,400,512 A - Document ID: US4400512A - Status: Granted - Kind: A - Application number: 06/220,560 - Filed: 1980-12-29 - Granted: 1983-08-23 - Earliest claimed: 1976-12-17 - Assignees: Rohm and Haas Company - Inventors: Joel Smolanoff - Web page: https://patentgrep.com/patent/US4400512A ## CPC - C07D 221/20: Spiro-condensed ring systems - A01N 33/08: containing oxygen or sulfur - A01N 43/34: having rings with one nitrogen atom as the only ring hetero atom - A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system - A01N 47/16: the nitrogen atom being part of a heterocyclic ring - A01N 47/38: containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof - C07C 45/75: Reactions with formaldehyde - C07C 47/36: containing hydroxy groups - C07D 209/54: Spiro-condensed - C07D 211/12: with only hydrogen atoms attached to the ring nitrogen atom - C07D 211/16: with acylated ring nitrogen atom - C07D 211/34: 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 211/70: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms - C07D 295/215: Radicals derived from nitrogen analogues of carbonic acid - C07D 317/26: Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom - C07D 317/30: 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 491/10: Spiro-condensed systems - 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 This invention relates to a method of using compounds selected from those of the following formula : ##STR1## wherein R.sup.1 is hydrogen, alkyl or alkenyl; R.sup.2 is hydrogen, alkyl, cycloalkyl or mononuclear aryl or R.sup.1 and R.sup.2, taken together with the carbon atom to which they are attached, form a cycloalkyl or cycloalkoxyalkyl; R.sup.3 is hydroxy, alkyl, alkoxycarbonyl, hydroxy lower alkyl or a radical of the formula: --C(.dbd.Y)NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen, alkyl, or alkenyl, R.sup.5 is alkyl, alkenyl carbalkoxy, or mononuclear aryl, or R.sup.4 and R.sup.5 may be joined together with the nitrogen atom to which they are attached to form a 5- to 7- membered heterocyclic ring having from 1 to 3 hetero atoms; Y is O or S; X is alkyl, alkoxycarbonylalkyl or cyano; m is an integer of 0 to 2 and n and n' are integers each having a value of 1 to 2 and the dotted line indicates an optional carbon to carbon double bond, compositions containing said compounds as insect repellents and to novel compounds. ## Claims ### Claim 1 A compound selected from the formula: ##STR20## wherein R.sup.1 and R.sup.2, taken together with the carbon atom to which they are attached, form cyclobutyl or cyclohexyl or cycloalkoxyalkyl ring of from 5 to 11 nuclear carbon atoms which ring may be saturated or unsaturated and substituted or unsubstituted where the substituent can be lower alkyl of 1 to 5 carbon atoms or hydroxy; R.sup.3 is a radical of the formula: --C(.dbd.Y)NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen and R.sup.5 is lower alkenyl of from 2 to 5 carbon atoms or carbo lower alkoxy or R.sup.4 and R.sup.5 may be joined to form, together with the nitrogen atom to which they are attached, pyrrolidinyl, piperidyl or homopiperidyl which may be substituted with a lower alkyl of from 1 to 5 carbon atoms, carbo alkoxy or ethylenedioxy; Y is O or S; X is lower alkyl of from 1 to 5 carbon atoms, lower alkoxy of from 1 to 5 carbon atoms, lower alkoxycarbonyl lower alkyl or cyano; m is an integer of 0 to 2 and n and n' are integers each having a value of 1 to 2 and the dotted line indicates an optional carbon to carbon double bond. ### Claim 2 (depends on 1) The compound of claim 1 wherein R.sup.3 is --C(.dbd.Y)NR.sup.7 R.sup.8 wherein R.sup.7 is hydrogen and R.sup.8 is lower alkoxycarbonyl or R.sup.7 and R.sup.8, taken together with the nitrogen atom to which they are attached are joined to form pyrrolidinyl or piperidynyl. ### Claim 3 A compound selected from the formula: ##STR21## wherein R.sup.7 and R.sup.8, taken together with the nitrogen atom to which they are attached, may be joined to form pyrrolidinyl, piperidyl or homopiperidyl which may be substituted with a lower alkyl, carbo lower alkoxy or ethylenedioxy; X.sup.1 is hydrogen, lower alkyl or lower alkoxycarbonyl; R.sup.9 and R.sup.10, taken together with the carbon atom to which they are attached, are joined to form cyclopentyl, cyclohexyl, cyclononyl, cyclodecyl, cyclohexylene, cycloheptylene, cyclononlene, bicyclo-(2.2.1)-heptyl or tetrahydropyranio; m' is an integer of from 0 to 2; n and n' are integers each having a value of 1 to 2 and the dotted line represents an optional carbon to carbon double bond. ### Claim 4 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undecylteteramethylene urea. ### Claim 5 (depends on 3) The compound of claim 3 named 3-azaspiro-[5.5]-undecyltetramethylene urea. ### Claim 6 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enylpentamethylene urea. ### Claim 7 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enyl carboethoxymethyl urea. ### Claim 8 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enetetramethylene urea. ### Claim 9 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enylallyl urea. ### Claim 10 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enyl-N',N'-diethyl urea. ### Claim 11 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enyl-N'-methyl-N'-dimethoxyethyl urea. ### Claim 12 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-2'-carbomethoxypyrolidinyl urea. ### Claim 13 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enyl-thiazolidinyl urea. ### Claim 14 (depends on 3) The compound of claim 3 named 2-azaspiro-[5.5]-undec-7-enyl-4'-carboethoxypiperidyl urea.