TH67702B - O-cyclopropyl-carboxanilide And use as a fungicide - Google Patents

Abstract

DC60 (23/05/56) Compounds with the formula (I): (Chemical formula) (I) Het is a 5- or 6-membered heterocyclic ring containing one to three hetero atoms, each group independently chosen from oxygen, nitrogen and sulfur, the ring is replaced by groups R4, R5 and R6; R1 is hydrogen or halo; R2 is hydrogen or halo; R3 which may be chosen to be replaced by a C2-12 alkyl, which may be chosen to be replaced by a C2-12 alkynyl, which may be chosen to be replaced by a C2-12 alkynyl, which may be chosen to be replaced by a C3-12 cycloalkyl, which may be chosen to be replaced by a phenyl or which may be chosen to be replaced by a heterocyclyl; and R4, R5 and R6 are, independently, chosen from hydrogen, halo, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4) alkyl and C1-4 haloalkoxy(C1-4) alkyl, if at least one of R4, R5 and R6 is not hydrogen. Compounds with formula (I) have plant-protective properties and are suitable for protecting plants against infestation by plant pathogenic microorganisms. Compounds with formula (I): (Chemical formula) (I) Het is a 5- or 6-membered heterocyclic ring of one to three hetero atoms, each group independently chosen from oxygen, nitrogen and sulfur, the ring is replaced by groups R4, R5 and R6; R1 is hydrogen or halo; R2 is hydrogen or halo; R3 The compounds with the formula (I) are chosen to have C2-12 alkyls replaced, C2-12 alkenyls replaced, C2-12 alkynyls replaced, C3-12 cycloalkyls replaced, phenyls replaced, or heterocyclyls replaced; and R4, R5, and R6 are, independently, chosen from hydrogen, halo, cyano, nitro, C1-4 alkyls, C1-4 haloalkyls, C1-4 alkoxy(C1-4)alkyls and C1-4 haloalkoxy(C1-4)alkyls, if at least one of R4, R5, and R6 is not hydrogen. The compounds with the formula (I) have phytoprotective properties and are suitable for protecting plants against pathogenic microorganisms.

Claims (10)

1. Compounds with the formula (I): (Chemical formula) (I) Het is pyrrolyl, pirazolyl or thiazolyl, each group substituted by groups R4, R5 and R6; R1 is hydrogen, fluoro, chloro or bromo; R2 is hydrogen, fluoro, chloro or bromo; R3 may be chosen to be a C2-12 alkyl substituted, where, when present, each substitute is, independently, chosen from fluoro, chloro, bromo, hydroxy, cyano, C1-4 alkoxy C(=O), formyl, nitro, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, HC(OR')=N and R'R''NN=C(H); may be chosen to be a C2-12 alkenyl substituted, where, when present, each substitute is, independently. Continuing, selected from Fluorochloro, chloro, bromo, hydroxycyano, C1-4 alkoxyC(=O), formyl nitro, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, HC(OR')=N and R'R''NN=C(H); which may be selected for C2-12 alkynil substitution, where, when present, each representative that is, independently, is selected from Fluorochloro, chloro, bromo, hydroxycyano, C1-4 alkoxyC(=O), formyl nitro, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 Haloalkylthio, HC(OR')=N and R'R''NN=C(H); which may be selected for substitution of C3-12 cycloalkyl, where, when present, each independent representative is selected from C1-3 alkyl, fluoro, chloro, bromo, hydroxy, cyano, C1-4 alkoxy C(=O), formyl, nitro, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, HC(OR')=N and R'R''NN=C(H), which may be selected for substitution of phenyl, where, when present, each independent representative is selected from C1-6 alkyl, fluoro, chloro, bromo, hydroxy, cyano, C1-4 alkoxy C(=O), formyl, nitro, C1-4 Alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, HC(OR')=N and R'R''NN=C(H) or a heterocyclyl substitute may be chosen, where, when present, each independent substitute is chosen from C1-6 alkyl, fluoro, chloro, bromo, hydroxy, cyano, C1-4 alkoxyC(=O), formyl, nitro, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, HC(OR')=N;R' and R'' is, independently, hydrogen or C1-4 alkyl; and R4, R5, and R6 are, independently, selected from hydrogen, fluoro, chloro, bromo, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4) alkyl, and C1-4 haloalkoxy(C1-4) alkyl, provided that at least one of R4, R5, and R6 is not hydrogen; and halo is fluoro, chloro, or bromo. 2. Compounds of formula (I) as claimed in claim 1, where Het means pyrrolyl, pirazolyl, thiazolyl, pyridinyl, pyrimidinyl, thiophenyl, furyl, isothiazolyl or isoxazolyl, each group replaced by groups R4, R5 and R6. 3. A compound of formula (I) as claimed under either claim 1 or claim 2, where R1 means hydrogen or fluorocarbon. 4. A compound of formula (I) is entitled to any one of the claims in claim 1, 2 or 3, where R2 means hydrogen or fluorocarbon. 5. Compounds of formula (I) are entitled to any one of claims 1, 2, 3 or 4, where R3 means C2-6 alkyl, which may be selectively substituted with C3-8 cycloalkyl, phenyl, thienyl or furyl. 6. A compound of formula (I) is entitled to any one of the claims 1, 2, 3, 4 or 5, where R4, R5 and R6 are, independently chosen from hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl and C1-4 alkoxy C1-4 alkyl; if at least one of R4, R5 and R6 is not hydrogen. 7. Compounds of formula (II): (chemical formula) (II) where R3 means as defined in either claim 1 or claim 5. 8. The process for the preparation of compounds of formula (II) as claimed in claim 7 is composed of a procedure by using a Pd (II)-ligand catalytic system, where the ligand is chosen from phosphine requiring a suitable molecular void to react with compounds of formula (XI) (chemical formula) (XI) with benzophenoneimene, which may be chosen in the presence of a base, to produce compounds of formula (XII) (chemical formula) (XII), where Hal means bromo or iodo; and R3 means as defined in claim 7. 9. A mixture for the control of microorganisms and prevention of attack and agglutination of plants by microorganisms, whereby the active ingredient means the compound of formulation (I) as claimed in claim 1 together with a suitable carrier. 10. Methods of controlling or preventing the aggregation of plants cultivated by pathogenic microorganisms to plants by using the compounds of formula (I) as claimed in claim 1 against plants, against certain parts of plants or locations of plants.