Pyrazolesulfonylurea derivative, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof

Claim 2

A compound represented by the formula (I): wherein A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups, haloalkyl groups, -CO 2 R (where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR 1 R 2 [where R 1 is a hydrogen atom, a C l -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken together may represent -(CH2) m - (m is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -], -S(O) n R 3 ( where R 3 is a C 1 -C 8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), -SO 2 NR 4 R 5 [where R 4 is a C 1 -C 8 alkyl group, R 5 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 4 and R 5 taken together may represent -(CH2) - (p is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -] or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C 1 -C 8 alkyl group; X and Y represent independently hydrogen atoms, halogen atoms, C 1 -C 8 alkyl groups, C 1 -C 8 alkoxy groups, C 1 -C 8 alkoxyalkyl groups, -CF 3 groups, C 1 -C 8 haloalkoxy groups, alkylamino goups, dialkylamino groups, (where R 6 and R 7 each represent hydrogen atoms or C 1 -C 8 alkyl groups) or either X or Y may form a five-membered ring containing an oxygen atom together with Z; and Z represents a nitrogen atom or C-R 8 (where R 8 represents a hydrogen atom, a haloalkyl group or may form a five-membered ring containing an oxygen atom together with X or Y).

Claim 3

A compound according to Claim 1, wherein A is a C 1 -C 4 alkyl group, a hydrogen atom or a phenyl group; B and C are independently selected from the group consisting of hydrogen atom, halogen atoms , C 1 -C 4 alkyl groups, -COOR (where R is allyl or a C 1 -C 4 alkyl group), -CF 3 , SO 2 -C 1 -C 4 -alkyl group, -SO 2 N(CH 3 ) 2 , -OCH 3 , -CONHC 1 -C 4 -alkyl, -CON(C 1 -C 4 -alkyl) 2 , -CON(CH 2 ) p (p is 4, 5 or 6) and phenyl group; D is a hydrogen atom; X and Y are independently selected from the group consisting of hydrogen atom, halogen atoms, C 1 -C 4 alkyl groups, C l -C 4 alkoxy groups, C 1 -C 4 alkoxyalkyl groups, -CF 3 and C 1 -C 4 haloalkoxy groups; and Z is N or CH .

Claim 4

A compound according to Claim 1, which is represented by the formula (II): wherein Alk represents methyl, ethyl, n-propyl or i-propyl; and X and Y are independently selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, n-propoxy and i-propoxy; and Z is N or CH.

Claim 5

A compound according to Claim 1, which is represented by the formula (III): wherein Alk is methyl or ethyl; X and Y are independently selected from the group consisting of methyl and methoxy; and Z is N or CH.

Claim 6

A compound according to Claim 4, wherein Y is methoxy and Z is CH.

Claim 7

A compound according to Claim 1, which is N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl] -1,3-dimethyl-5-methoxy-carbonylpyrazole-4-sulfonamide.

Claim 8

A compound according to Claim 1, which is N -[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyll-1,3-dimethyl-5-methoxycarbonyl-pyrazole-4-sulfonamide.

Claim 9

A compound according to Claim 1, wehich is N-[(4-chloro-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethyl-5-methoxy-carbonylpyrazole-4-sulfonamide.

Claim 10

A herbicidal composition which comprises a pyrazole sulfonamide derivative defined in Claim 1 as an active ingredient.

Claim 11

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protedted an effective amount of a compound of Claim 1.

Claim 12

A process for synthesizing a compound of the formula (I): wherein A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups, haloalkyl groups, -CO 2 R (where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR 1 R 2 [where R 1 is a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken together may represent -(CH2) m - (m is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -], -S(O) n R 3 ( where R 3 is a C 1 -C 8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), -SO 2 NR 4 R 5 [where R 4 is a C 1 -C 8 alkyl group, R 5 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 4 and R 5 taken together may represent -(CH2) - (p is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -] or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C 1 -C 8 alkyl group; X and Y represent independently hydrogen atoms, halogen atoms, C 1 -C 8 alkyl groups, C 1 -C 8 alkoxy groups, C 1 -C 8 alkoxyalkyl groups, -CF 3 groups, C 1 -C 8 haloalkoxy groups, alkylamino goups, dialkylamino groups, (where R 6 and R 7 each represent hydrogen atoms or C 1 -C 8 alkyl groups) or either X or Y may form a five-membered ring containing an oxygen atom together with Z; and Z represents a nitrogen atom or C-R 8 (where R 8 represents a hydrogen atom, a haloalkyl group or may form a five-membered ring containing an oxygen atom together with X or Y), which comprises allowing a compound represented by the formula (IV): wherein A, B and C are the same as defined above, to react with a compound represented by the formula (V): wherein D, X , Y and Z are the same as defined above.

Claim 13

A process for synthesizing a compound of the formula (I): wherein A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups, haloalkyl groups, -CO 2 R (where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR 1 R 2 [where R 1 is a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken together may represent -(CH2) m - (m is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -], -S(O) n R 3 ( where R 3 is a C 1 -C 8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), -SO 2 NR 4 R 5 [where R 4 is a C 1 -C 8 alkyl group, R 5 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 4 and R 5 taken together may represent -(CH2) - (p is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -] or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C 1 -C 8 alkyl group; X and Y represent independently hydrogen atoms, halogen atoms, C 1 -C 8 alkyl groups, C 1 -C 8 alkoxy groups, C 1 -C 8 alkoxyalkyl groups, -CF 3 groups, C 1 -C 8 haloalkoxy groups, alkylamino goups, dialkylamino groups, (where R 6 and R 7 each represent hydrogen atoms or C 1 -C 8 alkyl groups) or either X or Y may form a five-membered ring containing an oxygen atom together with Z; and Z represents a nitrogen atom or C-R 8 (where R 8 represents a hydrogen atom, a haloalkyl group or may form a five-membered ring containing an oxygen atom together with X or Y), which comprises allowing a compound represented by the formula (IV): wherein A, B and C are the same as defined above, to react with a compound represented by the formula (V): wherein D, X , Y and Z are the same as defined above.

Claim 14

A process for synthesizing a compound of the formula (I): wherein A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups, haloalkyl groups, -CO 2 R (where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR 1 R 2 [where R 1 is a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken together may represent -(CH2) m - (m is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -], -S(O) n R 3 (where R 3 is a C 1- C 8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), -SO 2 NR 4 R 5 [where R 4 is a C 1 -C 8 alkyl group, R 5 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 4 and R 5 taken together may represent -(CH2) - (p is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -] or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C 1 -C 8 alkyl group; X and Y represent independently hydrogen atoms, halogen atoms, C 1 -C 8 alkyl groups, C 1 -C 8 alkoxy groups, C 1 -C 8 alkoxyalkyl groups, -CF 3 groups, C 1 -C 8 haloalkoxy groups, alkylamino goups, dialkylamino groups or (where R 6 and R 7 each represent hydrogen atoms or C 1 -C 8 alkyl groups) or either X or Y may form a five-membered ring containing an oxygen atom together with Z; and Z represents a nitrogen atom or C-R 8 (where R 8 represents a hydrogen atom, a haloalkyl group or may form a five-membered ring containing an oxygen atom together with X or Y), which comprises allowing a compound represented by the formula (VII): wherein A, B and C are the same as defined above and R 9 represents an alkyl group or a phenyl group, to react with a compound represented by the formula (V): wherein D, X, Y and Z are the same as defined above.

Claim 15

A process for synthesizing a compound of the formula (I): wherein A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups, haloalkyl groups, -CO 2 R (where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR 1 R 2 [where R 1 is a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken together may represent -(CH2) m - (m is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -], -S(O) n R 3 (where R 3 is a C 1- C 8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), -SO 2 NR 4 R 5 [where R 4 is a C 1 -C 8 alkyl group, R 5 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 4 and R 5 taken together may represent -(CH2) - (p is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -] or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C 1 -C 8 alkyl group; X and Y represent independently hydrogen atoms, halogen atoms, C 1 -C 8 alkyl groups, C 1 -C 8 alkoxy groups, C 1 -C 8 alkoxyalkyl groups, -CF 3 groups, C 1 -C 8 haloalkoxy groups, alkylamino goups, dialkylamino groups or (where R 6 and R 7 each represent hydrogen atoms or C 1 -C 8 alkyl groups) or either X or Y may form a five-membered ring containing an oxygen atom together with Z; and Z represents a nitrogen atom or C-R 8 (where R 8 represents a hydrogen atom, a haloalkyl group or may form a five-membered ring containing an oxygen atom together with X or Y), which comprises allowing a compound represented by the formula (VII): wherein A, B and C are the same as defined above and R 9 represents an alkyl group or a phenyl group, to react with a compound represented by the formula (V): wherein D, X, Y and Z are the same as defined above.

Claim 16

A process for synthesizing a compound of the formula (IX): wherein A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups, haloalkyl groups, -CO 2 R (where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR1R2 [where R 1 is a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken together may represent -(CH2) m (m is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -], - S (O) n R 3 ( where R 3 is a C l -C 8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), -SO 2 NR 4 R 5 [where R 4 is a C 1 -C 8 alkyl group, R 5 is a hydrogen atom or a C l -C 8 alkyl group, or R 4 and R 5 taken together may represent -(CH2) p - (p is 4, 5 or 6), -CH 2 CH 2 0CH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -] or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C 1 -C 8 alkyl group; E represents a halogen atom; G represents a hydrogen atom, chlorine, bromine, C 1 - 4 alkyl, CF 3 , methoxymethyl or methoxyethyl; and Z represents a nitrogen atom or C-R 8 (where R 8 represents a hydrogen atom or a haloalkyl group), which comprises allowing a compound represented by the formula (VI): to react with a compound represented by the formula (X): wherein E, G and Z are the same as defined above.

Claim 17

A process for synthesizing a compound of the formula (IX): wherein A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; B and C represent independently hydrogen atoms, halogen atoms, nitro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups, haloalkyl groups, -CO 2 R (where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR1R2 [where R 1 is a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken together may represent -(CH2) m (m is 4, 5 or 6), -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -], - S (O) n R 3 ( where R 3 is a C l -C 8 alkyl group, a phenyl group or an arylalkyl group and n is 0, 1 or 2), -SO 2 NR 4 R 5 [where R 4 is a C 1 -C 8 alkyl group, R 5 is a hydrogen atom or a C l -C 8 alkyl group, or R 4 and R 5 taken together may represent -(CH2) p - (p is 4, 5 or 6), -CH 2 CH 2 0CH 2 CH 2 - or -CH 2 CH 2 N(CH 3 )CH 2 CH 2 -] or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups; D represents a hydrogen atom or a C 1 -C 8 alkyl group; E represents a halogen atom; G represents a hydrogen atom, chlorine, bromine, C 1 - 4 alkyl, CF 3 , methoxymethyl or methoxyethyl; and Z represents a nitrogen atom or C-R 8 (where R 8 represents a hydrogen atom or a haloalkyl group), which comprises allowing a compound represented by the formula (VI): to react with a compound represented by the formula (X): wherein E, G and Z are the same as defined above.