Nissan Chemical Industries Limited

Eiichi Oya

Tsutomu Nawamaki

Takuya Kakuta

Masatoshi Baba

Shigeomi Watanabe

Norio Tanaka

Takashi Ikai

Yasuo Kawamura

Koichi Suzuki

Kimihiro Ishikawa

Katsushi Morimoto

Susumu Yamamoto

Hiroshi Kita

Toshiaki Sato

Hisashi Nakata

Kunimitsu Nakahira

Chiaki Kawaguchi

Yoshitake Tamada

Kenji Hattori

Kanji Sawada

Kaoru Itoh, Deceased

Kenichi Shiojima

Jun Satow

Takasi Ikai

Junichi Watanabe

Yasuo Kondo

Kaoru Itoh

Kenzo Fukuda

Yoichi Ito

Seiichi Fujii

Kakuta Takuya

The present invention provides a nitrogen-containing cyclic compound represented by the formula (1): ##STR1## wherein R.sup.1 represents an alkyl group; R represents a hydrogen atom or an alkyl group; X represents an oxygen or sulfur atom or NR.sup.3 ; Q.sup.1 represents a hydrogen atom, or an alkyl, cycloalkyl, alkenyl or alkynyl group or a phenyl, naphthyl or heterocyclic group etc.; Q.sup.2 represents an alkyl, cycloalkyl or alkenyl group, or a phenyl or thienyl group etc.; A.sup.1 represents a carbon or nitrogen atom; A.sup.2 represents CR.sup.2 or NR.sup.2, or an oxygen or sulfur atom, or SO or SO.sub.2 ; A.sup.3 represents a single bond, or an oxygen or sulfur atom, or CR.sup.5 or NR.sup.5) and a herbicide comprising the same, which herbicide exhibits very high herbicidal activity at very low application rate and has selectivity against crops.

Pyrimidone isobutyric acid and herbicides containing the same

Nitrogen-containing cyclic compounds and herbicides containing the same

2-arylaminopyrimidinone derivative, and herbicide and plant growth

The present invention provides a method for preparing a 4-alkylsulfonyl-2-chloro-m-xylene useful as an intermediate for agricultural chemicals.

Method for preparing 4-alkylsulfonyl-2-chloro-m-xylene

The present invention provides a method for preparing a 4-alkylsulfonyl-2-chloro-m-xylene useful as an intermediate for agricultural chemicals, and an intermediate for the production thereof. The method of the present invention is to produce (E) from (C) by way of novel intermediates (D-1) and (D-2). ##STR1##

A pyrazole derivative having the formula ##STR1## is disclosed; the groups A, B, Q, V, W, X, Y, and Z are defined in the description.

Benzoic acid derivatives useful as intermediates for the preparation of

A substituted benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, cyano, nitro or halogen; X.sub.2 is --L--OR.sub.1 (wherein L is C.sub.1 -C.sub.4 alkylene or C.sub.1 -C.sub.4 alkylidene, and R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl), --L--O--L--OR.sub.1 (wherein L and R.sub.1 are as defined above), --L--S(O).sub.n --R.sub.2 (wherein L is as defined above, R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl, and n is an integer of 0, 1 or 2), --L--O--COR.sub.2 (wherein L and R.sub.2 are as defined above), --L--NR.sub.1 R.sub.3 (wherein L and R.sub.1 are as defined above, and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl), --COOR.sub.1 (wherein R.sub.1 is as defined above) or --COO--L--O--R.sub.1 (wherein L and R.sub.1 are as defined above), provided that when X.sub.1 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl, X.sub.2 is not --COOR.sub.1 ; X.sub.3 is trifluoromethyl, C.sub.1 -C.sub.3 alkoxy, halogen, cyano, nitro or --S(O).sub.n R.sub.4 (wherein n is as defined above, and R.sub.4 is C.sub.1 C.sub.3 alkyl); X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; X.sub.5 is hydrogen or fluorine; and each of Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; or a salt thereof.

Substituted benzoyl derivatives and selective herbicides

A process for producing a 4-benzoyl-5-hydroxylpyrazole of the formula III: ##STR1## which comprises reacting carbon monoxide and a 5-hydroxypyrazole of the formula II: ##STR2## with a substituted benzene of the formula I: ##STR3## in the presence of a base and a catalyst of Group VIII of the Periodic Table.

Substituted benzenes useful as intermediates

A pyrazole derivative of the formula I ##STR1## wherein A is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl; B is hydrogen, C.sub.1 -C.sub.3 alkyl, halogen, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl or C.sub.2 -C.sub.4 alkoxycarbonyl; X is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, nitro, cyano, etc.; Y is --OR.sup.1 (wherein R.sup.1 is C.sub.3 -C.sub.8 cycloalkyl, etc), --O--L--O--R.sup.1 (wherein L is C.sub.1 -C.sub.6 alkylene which may be substituted by C.sub.1 -C.sub.3 alkyl), --O--L--OH, --O--L--O--L--O--R.sup.2 (wherein R.sup.2 is hydrogen, C.sub.1 -C.sub.6 alkyl group, etc.), --O--L--R.sup.3 (wherein R.sup.3 is phenyl which may be substituted by C.sub.1 -C.sub.3 alkyl, etc.), --O--M (wherein M is a 3- to 6-membered alicyclic group), --O--L--M, --O--L--NR.sup.4 R.sup.5 (wherein each of R.sup.4 and R.sup.5 is hydrogen or C.sub.1 -C.sub.6 alkyl, or R.sup.4 and R.sup.5 form a ring together with the adjacent nitrogen atom), --O--L--COOR.sup.4, --O--CH.dbd.CH--COOR.sup.4, --O--L--CN, --O--L--C(O)--R.sup.2, --O--L--S(O).sub.n --R.sup.4 (wherein n is an integer of from 0 to 2), --O--COOR.sup.4, --O--CONR.sup.4 R.sup.5, --OP(O)(OR.sup.4).sub.2, --S(O).sub.n R.sup.1, or --S(O).sub.n --L--O--R.sup.1 ; Z is halogen, nitro, C.sub.1 -C.sub.3 alkoxy, etc.; V is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; W is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, etc.; Q is hydrogen, C.sub.1 -C.sub.6 alkyl which may be substituted by halogen, . . . --C(O)--R.sup.7 (wherein R.sup.7 is phenyl which may be substituted), --S(O).sub.2 R.sup.7, --P(O)(OR.sup.7).sub.2, --L--C(O)--R.sup.7, --L--C(O)--N(R.sup.8)(R.sup.9) (wherein each of R.sup.8 and R.sup.9 is hydrogenor C.sub.1 -C.sub.6 alkyl), --L--R.sup.10 (wherein R.sup.10 is phenyl group may be substituted, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.7 alkoxy, or hydroxyl), --L--N(R.sup.8)(R.sup.9), --L--OR.sup.11 (wherein R.sup.11 is hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkenyl), --L--OC(O)R.sup.12 (wherein R.sup.12 is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy), --L--S(O).sub.n R.sup.11, --L--SC(O)R.sup.8, ##STR2## (wherein each of L1 and L2 is methylene, oxygen or sulfur, R.sup.12 is hydrogen or C.sub.1 -C.sub.3 alkyl, and m is 2 or 3); and a salt thereof.

Pyrazole derivatives and herbicides containing them

An herbicidally effective benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkoxy or halogen;

A pyrazole derivative having the formula: ##STR1## wherein A is alkyl, alkenyl or alkynyl; B is hydrogen, alkyl, halogen, haloalkyl, alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl or alkoxycarbonyl; X is alkyl, alkoxy, halogen, nitro, cyano, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl substituted by hydrogen or alkyl, haloalkoxy, alkylthio or alkylthioalkyl; Y is --COOR1 (wherein R1 is hydrogen, alkyl, etc.), --COO--L--OR1 (wherein L is alkylene which may be substituted), --COO--L--R2 (wherein R2 is phenyl group which may be substituted), --COO--M (wherein M is 3 to 6-membered alicyclic residue containing not more than 2 sulfur or oxygen atoms), --COO--L--M, --COO--L--O--L--R2, --COO--L--S(O).sub.n --CON (R3) (R4) (wherein each of R3 and R4 is hydrogen, alkyl, etc.), a --CON--(CH.sub.2).sub.n, ##STR2## wherein R5 is alkyl), ##STR3## --CONHSO.sub.2 CH.sub.3, --CONHSO.sub.2 CF.sub.3, --COO--L--N(R3) (R4), --COO--L--CO--R1, --COO--L--CO--O--R1, --COO--L--CN, --Coo--L--NO.sub.2 --COOSi (R5).sub.3, --COO--N.dbd.(R6) (R7) (wherein each of R6 and R7 is alkyl), --COO--N.dbd.C--(CH.sub.2).sub.n, --COO--L--O--SO.sub.2 --R1, --Coo--L--O--CO--R1, --COO--L--O--L--O--R1, --COO--L--Si (R5).sub.3, --C(O)S--R1, --C(S)O--R1, --C(S)S--R1, --L--O--R1, --L--O--L--O--R8 (wherein R8 is hydrogen or alkyl), --L--O--M, --L--O--L--M, --L--NR8R9 (wherein R9 is alkyl group), --L--O--CH.sub.2 Ph, --L--O--L--COOR9, --L--CN, --L--S(O).sub.n --R1, --L--S--L--O--R9, --L--O--COR9, --L--O--SO.sub.2 R9, --L--COOR8, --C.dbd.CHOR8 or --L--O--L--CN; Z is halogen, nitro, alkoxy, trifluoromethyl, cyano or --S(O).sub.n R10 (wherein R10 is alkyl or haloalkyl); V is a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms or an alkoxy group having from 1 to 4 carbon atoms; W is a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, a haloalkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an alkoxyalkyl group having from 2 to 6 carbon atoms, an alkoxycarbonyl group having from 2 to 5 carbon atoms, a haloalkoxy group having from 1 to 3 carbon atoms, a nitro group, a cyano group or a --S(O).sub.n --R group (wherein n is as defined above and R is an alkyl group having from 1 to 4 carbon atoms); Q is hydrogen, alkyl, alkenyl, alkynyl, cyanomethyl, --C(O)--R11 (wherein R11 is phenyl group which may be substituterd, alkyl, alkoxy or hydroxyl), --S(O).sub.2 R11, --P(O) (OR11).sub.2 --L--C(O)--R11, --L--C(O)--N (R12) (R13) (wherein each of R12 and R13 is hydrogen or alkyl), --L--R14 (wherein R14 is phenyl which may be substituted, alkyl, alkoxy or hydroxy), --L--N(R12) (R13), a --L--OR15 (wherein R15 is hydrogen, alkyl or alkenyl), --L--OC(O)R16 (wherein R16 is alkyl or alkoxy), --L--S(O).sub.n R15, --L--SC(O)R12, ##STR4## wherein each of L1 and L2 is methylene, oxygen is sulfur and R16 is hydrogen or alkyl), and a salt thereof, useful as a herbicide.

Pyrazole derivative and herbicide containing it

A process for producing a 4-benzoyl-5-hydroxylpyrazole of the formula III: ##STR1## which comprises reacting carbon monoxide and a 5-hydroxypyrazole of the formula II: ##STR2## to a substituted benzene of the formula I: ##STR3## wherein X is a bromine atom, an iodine atom or a diazonium tetrafluoroboron salt group, in the presence of a base and a catalyst of Group VIII of the Periodic Table.

Process for producing 4-benzoyl-5-hydroxypyrazoles

A pyrazole derivative having the formula: ##STR1## where A, B, X, Y, Z and Q are described below.

Herbicidal pyrazole derivatives

A process for growing wheat and selectively preventing or controlling the growth of wild oats in the same site in which the wheat is being cultivated which comprises applying to said site an amount of an active compound sufficient to control the growth of wild oats without adversely affecting the growth of the wheat, said active compound being N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-3-methyl-1 -(2-pyridyl)pyrazole-5-sulfonamide or N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-4-methoxycarbonyl-1-(2-pyrid yl)pyrazole-5-sulfonamide.

Wheat growing process utilizing selective herebicide

Disclosed are a pyrazolesulfonamide derivative represented by Formula (I): ##STR1## wherein B, D, Q, E, W and G have the same meaning as defined in the specification, a process for its production and a herbicide containing it.

Growing community of inventors

Funabashi, Japan

Eiichi Oya