Patent EA-002341-B1 (EA)
Title: 1-aryl-3-iminopyrazoles, processes for the preparation thereof and use as pesticedes
Inventor: MANNING DAVID TREADWAY
IPC: C07D231/38
Filed: 1998-03-09
Abstract: 1. A compound of formula (I):   wherein R31 is amino; C1-C20 optionally substituted by one or more R35;phenyl substituted by R36 or R37; R38; NH-CO-NH-N=CR8R9; NH-CS-NH-N=CR8R9; NH-CO-NR8R9; NH-CS-NR8R9; NH-CO-OR8; or NH-CS-OR8; R32 is C1-C6 alkyl, preferably methyl; R33 is a lone pair of electrons or an oxygen, preferably a lone pair of electrons; R35 is halogen, amino, C1-C6 alkylamino, di(C1-C6 alkyl)amino, NO2, CN, C1-C6 alkoxy, (C1-C6 alkoxy)carbonyl, hydroxycarbonyl, (C1-C6 alkyl)carbonyl, methylene, methylidyne, C1-C6 alkynyl, alkylalkynyl (C1-C6 alkyl; C1-C6 alkynyl); or R35 may be phenyl optionally substituted by one or more R36; or R35 may be a heterocyclic ring having a total of 3 to 7 ring atoms of which 1 to 4 are heteroatoms, said heteroatoms being the same or different and being selected from the group consisting of O, S and N, said heterocyclic ring being saturated or unsaturated and being optionally substituted by one or more R36; or R35 may be OH, SH, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, aminocarbonyl, (C1-C6 alkyl)aminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkoxy)carbonyl, or P(O)(OR8)(OR9); R36 may be SF5, halogen, C1-C6 alkyl, C1-C6 hydroxyalkyl, NO2, CN, amino, C1-C6 alkylamino, di(C1-C6 alkyl)amino, di(C1-C6 alkyl)aminocarbonylamino, (C1-C6 alkyl)aminocarbonylamino, aminocarbonylamino, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)carbonylamino, (C1-C6 alkoxy)carbonylamino, aminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkyl)aminocarbonyl, hydroxycarbonyl, aminocarbonyloxy, (C1-C6 alkyl)aminocarbonyloxy, di(C1-C6 alkyl)aminocarbonyloxy, hydroxy, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, P(O)(OR8)(OR9), (C1-C6 alkyl)[( C1-C6 alkyl)carbonyl]amino or phenylamino(C1-C6 alkyl); R37 may be R36 or phenyl optionally substituted by one or more R36, phenoxy optionally substituted by one or more R36, or benzyl optionally substituted by one or more R36; R38 is a heterocyclic radical derived from a single heterocyclic ring or from a two ring fused heterocyclic system at least one ring of which is heterocyclic, each ring having 3 to 7 ring atoms, each heterocyclic ring having 1 to 4 hetero ring atoms, said hetero ring atoms being the same or different and being selected from the group consisting of O, S and N, each ring being saturated or unsaturated; such heterocyclic radicals may be, for example, radicals deriving from the following compounds: pyridine, pyrimidine, oxazole, oxadiazole, oxatriazole, isoxazole, thiazole, isothiazole, imidazole, pyrane, pyrone, pyrazole, pyrrole, tetrazole, furoxan, tetrahydrofuranyl, furan, pyrazine, pyridazine, benzimidazole, quinoline, isoquinoline, triazine, thiophene, furopyran, furopyrone, thiatriazine, thiadiazole, all of which heterocyclic radicals can be attached to the nitrogen of the R32-C=N-R31 group at any possible position of the heterocyclic ring and all of which rings may be optionally substituted with one or more R36 or phenyl optionally substituted with one or more R36; R8 and R9 are independently selected from H and C1-C6 alkyl optionally having one or more substituents selected from the group consisting of halogen, NO2, CN, CHO, OH, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, (C1-C6 alkoxy)carbonyl, hydroxycarbonyl, and carbamoyl; R4 is S(O)nR11; R11 is methyl or ethyl; n is 0, 1, preferably 1; R5 is NR8R9, preferably NH2 or NHR9;; Z is C-R16; R12 is chlorine or bromine; R13 and R15 are H; R14 is perhaloalkyl, perhaloalkoxy, or SF5, preferably CF3, OCF3 or SF5; R16 is chlorine or bromine; and pesticidally acceptable salts thereof. 2. The compound according to claim 1 wherein R32 is CH3; R4 is S(O)nR11; and R11 is methyl or ethyl. 3. The compound according to any one of the foregoing claims wherein R14 is CF3, OCF3 or SF5 and R12 and R16 are chlorine and bromine. 4. A composition comprising a compound of formula (I) as defined in any one of Claims 1-3, or a pesticidally acceptable salt thereof, and a pesticidally acceptable carrier. 5. A method for controlling pests at a locus, said method comprising applying to said locus a pesticidally effective amount of a compound of formula (I) or a pesticidally acceptable salt thereof as defined in any one of claims 1-3 or a composition as defined in claim 4. 6. A method according to Claim 5 wherein the locus is an area used or to be used for the growing of crops. 7. A process for the preparation of a compound as claimed in Claim 1, wherein R33 is a lone electron pair, said process comprising reacting a compound having the formula:   wherein R34 is an oxygen atom and the remaining structural variables are as defined in Claim 1, with an amine having the formula R31-NH2             (III) wherein R31 is as defined in Claim 1. 8. A process for the preparation of a compound as defined in Claim 1 wherein R33 is an oxygen or sulfur atom, said process comprising reacting a compound having the formula   wherein R34 is an oxygen atom and the remaining structural variables are as defined in Claim 1, with an amine having the formula R31 - NHOH wherein R31 is as defined in Claim 1.