# US 5,705,516 A · Oxazoles and their agricultural compositions

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- Number: US 5,705,516 A
- Document ID: US5705516A
- Status: Granted
- Kind: A
- Application number: 08/400,912
- Filed: 1995-03-08
- Granted: 1998-01-06
- Earliest claimed: 1994-03-10
- Assignees: Zeneca Limited
- Inventors: Michael Drysdale Turnbull; Alison Mary Smith; Roger Salmon
- Web page: https://patentgrep.com/patent/US5705516A

## CPC

- C07D 213/70: Sulfur atoms
- A01N 33/22: having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
- A01N 43/08: with oxygen as the ring hetero atom
- A01N 43/10: with sulfur as the ring hetero atom
- A01N 43/40: six-membered rings
- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/64: having rings with three nitrogen atoms as the only ring hetero atoms
- A01N 43/66: 1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N 43/707: 1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
- A01N 43/713: having rings with four or more nitrogen atoms as the only ring hetero atoms
- A01N 43/74: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 43/82: five-membered rings with three ring hetero atoms
- C07C 17/087: to unsaturated halogenated hydrocarbons
- C07C 17/23: by dehalogenation
- C07C 323/09: having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07D 213/71: to which a second hetero atom is attached
- C07D 213/80: in position 3
- C07D 213/82: in position 3
- C07D 213/85: in position 3
- C07D 231/18: One oxygen or sulfur atom
- C07D 231/28: Two oxygen or sulfur atoms
- C07D 231/30: attached in positions 3 and 5
- C07D 233/86: Oxygen and sulfur atoms, e.g. thiohydantoin
- C07D 233/90: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 233/92: attached in position 4 or 5
- C07D 237/18: Sulfur atoms
- C07D 237/30: Phthalazines
- C07D 241/18: Oxygen or sulfur atoms
- C07D 241/44: 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 carbon atoms of the hetero ring
- C07D 251/22: to two ring carbon atoms
- C07D 253/04: 1,2,3-Triazines
- C07D 253/07: 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 253/075: Two hetero atoms, in positions 3 and 5
- C07D 253/10: Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
- C07D 257/04: Five-membered rings
- C07D 261/10: 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 261/18: Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
- C07D 263/34: 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 263/46: Sulfur atoms
- C07D 271/07: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D 271/113: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D 275/03: 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 277/36: Sulfur atoms
- C07D 277/56: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 277/58: Nitro radicals
- C07D 285/08: 1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- C07D 285/125: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D 285/135: Nitrogen atoms
- C07D 307/64: Sulfur atoms
- C07D 333/34: Sulfur atoms
- 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
- C07D 333/62: 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 carbon atoms of the hetero ring
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 471/04: Ortho-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

A compound having the formula R--S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2, wherein R is a phenyl group or a heterocyclic group selected from furyl, thienyl, isoxazolyl, isothiazolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thidiazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,3,4-triazinyl, and 1,3,5-triazinyl groups, said phenyl or heterocyclic group being optionally substituted by optionally substituted alkyl, optionally substituted alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, alkoxy, alkenyloxy, alkynyloxy, hydroxyalkyl, alkoxyalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxy, optionally substituted heteroarylalkoxy, optionally substituted heteroaryloxyalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, halogen, hydroxy, cyano, nitro, --NR7R8, --NR7COR8, --NR7CSR8, --NR7SO2R8, --N(SO2R7)(SO2R8), --COR7, --CONR7R8, -alkylCONR7R8, --CR7NR8, --COOR7, --OCOR7, --SR7, --SOR7, --SO2R7, -alkylSR7, -alkylSOR7, -alkylSO2R7, --OSO2R7, --SO2NR7R8, --CSNR7R8, --SiR7R8R9, --OCH2CO2R7, --OCH2CH2CO2R7, --CONR7SO2R8, -alkylCONR7SO2R8, --NHCONR7R8, --NHCSNR7R8, or an adjacent pair of R1, R2, R3, R4, R5 and R6 when taken together form a fused 5- or 6-membered carbocyclic or heterocyclic ring; R7, R8 and R9 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, alkynyl, optionally substituted aryl or optionally substituted arylalkyl, haloalkyl, haloalkenyl, haloalkynyl, halogen or hydroxy.

## Claims

### Claim 1

A compound of formula (I),
R--S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2
or a salt thereof, wherein n is 0, 1 or 2; and R is a group of formula (IV) or (VI) ##STR22## wherein the S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 group is at least one of R.sup.2, R.sup.3, R.sup.4 or R.sup.5 ; and the remainder of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, alkoxy, alkenyloxy, alkynyloxy, hydroxyalkyl, alkoxyalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxy, optionally substituted heteroarylalkoxy, optionally substituted heteroaryloxyalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, halogen, hydroxy, cyano, nitro, --NR.sup.7 R.sup.8, --NR.sup.7 COR.sup.8, --NR.sup.7 CSR.sup.8, --NR.sup.7 SO.sub.2 R.sup.8, --N(SO.sub.2 R.sup.7)(SO.sub.2 R.sup.8), --COR.sup.7, --CONR.sup.7 R.sup.8, -alkylCONR.sup.7 R.sup.8, --CR.sup.7 NR.sup.8, --COOR.sup.7, --OCOR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, -alkylSR.sup.7, -alkylSOR.sup.7, -alkylSO.sub.2 R.sup.7, --OSO.sub.2 R.sup.7, --SO.sub.2 NR.sup.7 R.sup.8, --CSNR.sup.7 R.sup.8, --SiR.sup.7 R.sup.8 R.sup.9, --OCH.sub.2 CO.sub.2 R.sup.7, --OCH.sub.2 CH.sub.2 CO.sub.2 R.sup.7, --CONR.sup.7 SO2R.sup.8, -alkylCONR.sup.7 SO.sub.2 R.sup.8, --NHCONR.sup.7 R.sup.8, --NHCSNR.sup.7 R.sup.8 ; and R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, alkynyl, optionally substituted aryl or optionally substituted arylalkyl, haloalkyl, haloalkenyl, haloalkynyl, halogen, or hydroxy.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein:
the --S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 group is at least one of R.sup.2, R.sup.3, R.sup.4 or R.sup.5 ;
and the remainder of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, optionally substituted C.sub.1-6 alkyl, optionally substituted C.sub.2-6 alkenyl, optionally substituted C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.4-7 alkylcycloalkyl, C.sub.1-6 alkoxy, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy, C.sub.1-6 hydroxyalkyl, C.sub.2-6 monoalkoxyalkyl, C.sub.3-6 dialkoxyalkyl, optionally substituted C.sub.6-10 aryl, optionally substituted C.sub.6-10 aryl-C.sub.1-2 alkyl group, optionally substituted 5 or 6 membered heteroaryl, optionally substituted 5 or 6 membered heteroaryl-C.sub.1-6 alkyl, optionally substituted C.sub.6-10 aryloxy, optionally substituted C.sub.6-10 aryl-C.sub.1-2 alkoxy, C.sub.6-10 aryloxy-C.sub.1-6 alkyl, optionally substituted 5 or 6 membered heteroaryloxy, optionally substituted 5 or 6 membered heteroaryl-C.sub.1-6 alkoxy, 5 or 6 membered heteroaryloxy-C.sub.1-2 alkyl, C.sub.1-6 haloalkyl, C.sub.2-6 haloalkenyl, C.sub.2-6 haloalkynyl, C.sub.1-6 haloalkoxy, C.sub.2-6 haloalkenyloxy, C.sub.2-6 haloalkynyloxy, halogen, hydroxy, cyano, nitro, --NR.sup.7 R.sup.8, --NR.sup.7 COR.sup.8, --NR.sup.7 CSR.sup.8, --NR.sup.7 SO2R.sup.8, --N(SO.sub.2 --R.sup.7)(SO.sub.2 --R.sup.8), --COR.sup.7, --CONR.sup.7 R.sup.8, --C.sub.1-6 alkylCONR.sup.7 R.sup.8, --CR.sup.7 NR.sup.8, --COOR.sup.7, --OCOR.sup.7, --SR.sup.7, --SOR.sup.7, --SO.sub.2 R.sup.7, --C.sub.1-6 alkylSR.sup.7, --C.sub.1-6 alkylSOR.sup.7, --C.sub.1-6 alkyl-SO.sub.2 R.sup.7, --OSO.sub.2 R.sup.7, --SO.sub.2 NR.sup.7 R.sup.8, --CSNR.sup.7 R.sup.8, --SiR.sup.7 R.sup.8 R.sup.9, --OCH.sub.2 CO.sub.2 R.sup.7, --OCH.sub.2 CH.sub.2 CO.sub.2 R.sup.7, --CONR.sup.7 SO.sub.2 R.sup.8, --C.sub.1-6 alkylCONR.sup.7 SO.sub.2 R.sup.8, --NHCONR.sup.7 R.sup.8, --NHCSNR.sup.7 R.sup.8 ;
and R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, optionally substituted C.sub.1-6 alkyl, optionally substituted C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 haloalkyl, C.sub.2-6 haloalkenyl, C.sub.2-6 haloalkynyl, optionally substituted C.sub.4-6 aryl or optionally substituted C.sub.4-6 aryl-C.sub.1-6 alkyl, halogen or hydroxy.

### Claim 3 (depends on 2)

A compound according to claim 2, wherein when any one of R.sup.2 to R.sup.5 is:
substituted alkyl, or contains a substituted alkyl moiety, comprising one or more substituents, the substituents are chosen from halogen, nitro, cyano, --COOR.sup.7 or a salt thereof, hydroxy, alkoxy, alkoxyimino, alkoxycarbonyl, carbamyl, mono- or di-alkylcarbamoyl, amino, mono- or di-alkylamino, acylamido, alkanesulfonyl and arylsulfonyl;
substituted alkenyl, or contains a substituted alkenyl moiety, comprises one or more substituents, the substituents are chosen from halogen, COOR.sup.7 or a salt thereof, hydroxy, nitro and cyano;
substituted aryl or heteroaryl, or contains a substituted aryl or heteroaryl moiety, comprises one or more substituents, the substituents are chosen from alkyl, alkoxy, haloalkyl, halogen, hydroxy, COOR.sup.7 or a salt thereof, aminosulfonyl, cyano and nitro.

### Claim 4 (depends on 3)

A compound according to claim 3 wherein when any one of R.sup.2 to R.sup.5 is --SR.sup.7, then --SR.sup.7 is optionally substituted C.sub.1-6 alkylthio, C.sub.2-6 alkenylthio, C.sub.2-6 alkynylthio, C.sub.1-6 haloalkyl, C.sub.2-6 haloalkenylthio, C.sub.2-6 haloalkynylthio or C.sub.6-10 arylthio.

### Claim 5 (depends on 1)

A compound according to claim 1 wherein:
at least one of R.sup.2 to R.sup.5 is the --S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 group;
and the remainder of R.sup.2 to R.sup.5 are each independently hydrogen; nitro; halogen; cyano; --CH.dbd.NOH; C.sub.1-4 alkyl; C.sub.1-4 haloalkyl; C.sub.1-4 alkenyl; C.sub.1-4 haloalkenyl; cyclopropyl; hydroxy; C.sub.1-4 alkoxy; C.sub.2-4 alkoxyalkyl; --COOH; C.sub.2-4 alkoxycarbonyl; C.sub.2-4 haloalkenyloxycarbonyl; --CONH.sub.2 ; mono or di-C.sub.1-2 alkylaminocarbonyl; C.sub.2-4 alkanecarbonyl; phenyl optionally mono- or di-substituted with groups independently chosen from halogen, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or aminosulfonyl; --CONHSO.sub.2 --C.sub.1-4 alkyl; benzyl optionally mono- or di-substituted with groups independently chosen from halogen, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; phenoxy optionally mono- or di-substituted with groups independently chosen from halogen, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; amino optionally mono- or di-substituted with C.sub.1-4 alkyl groups; --SH; C.sub.1-4 alkylthio; benzylthio optionally mono- or di-substituted with groups independently chosen from halogen or C.sub.1-4 haloalkyl; C.sub.1-4 alkenylthio; C.sub.2-4 haloalkenylthio; a second S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 group; C.sub.1-4 alkanesulfonyl; C.sub.1-4 haloalkanesulfonyl; fluorosulfonyl; mono- or di-C.sub.1-4 alkylsulfamoyl; a 5 or 6 membered heteroaryl group optionally substituted with halogen.

### Claim 6 (depends on 1)

A compound according to claim 1 wherein the S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 group is at least one of R.sup.2, R.sup.3, R.sup.4 or R.sup.5 ; and the remainder of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, haloalkyl, halogen, cyano, nitro, --COR.sup.7, --CONR.sup.7 R.sup.8, --COOR.sup.7, --SO.sub.2 R7, --SO.sub.2 NR.sup.7 R.sup.8, --CONR.sup.7 SO2R.sup.8, and R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, optionally substituted alkyl, halogen, or hydroxy.

### Claim 7 (depends on 1, 2, 3, 4, 5)

An agricultural nematicidal, insecticidal or acaricidal composition comprising a nematicidally, insecticidally, or acaricidally effective amount of a compound of any one of claims 1 to 5 as the active ingredient, in admixture with an agriculturally acceptable diluent or carrier.

### Claim 8 (depends on 7)

An agricultural composition according to claim 7, further comprising a surface active material.

### Claim 9 (depends on 7, 8)

An agricultural composition according to either of claims 7 and 8, further comprising at least one other active ingredient which is an insecticide, fungicide, bactericide, acaricide or other biologically active compound.

### Claim 10 (depends on 1, 2, 3, 7, 8, 9)

A process for preparing an agricultural composition of any one of claims 7 to 9, comprising admixing the compound of any one of claims 1 to 3 and the agriculturally acceptable diluent or carrier.

### Claim 11 (depends on 1, 2, 3, 4, 5, 7, 8, 9)

A method for killing or controlling nematode, insect or acarid pests comprising applying an effective amount of a compound of any one of claims 1 to 5, or a composition of any one of claims 7 to 9, to the pests, their habitat, or a plant susceptible to attack by the pests.