Nissan Chemical Industries Limited

Rohm and Haas Company

Masatoshi Baba

Norio Tanaka

Eiichi Oya

Tsutomu Nawamaki

Takuya Kakuta

Takashi Ikai

Masayoshi Hirose

Shigeomi Watanabe

Kiminori Hirata

Yoshinori Ochiai

Masakazu Taniguchi

Norihito Hayakawa

Yasuo Kawamura

Koichi Suzuki

Shigeru Ishii

Tomoyuki Ogura

Takasi Ikai

Masaji Matsunaga

Norihiro Suwa

Kazuhiro Yamagishi

Hideo Suzuki

Masaki Kudo

Thifluzamide with improved efficacy

The disclosed invention is thifluzamide with an altered crystalline form, prepared by heat-melting and then cooling, and agricultural chemical compositions comprising such a thifluzamide as its effective ingredient.

Thifluzamide with stabilized efficacy

The disclosed invention provides agricultural chemical compositions containing active carbon-treated thifluzamide as an effective ingredient. Such compositions provide increased release of thifluzamide into water.

Agricultural chemical compositions with improved thifluzamide release in

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

Compounds of the formula: ##STR1## wherein R is a member selected from the group consisting of lower alkyls having from 2 to 4 carbon atoms; and chlorine and bromine. The compounds are useful as active ingredients in, e.g., insecticidal, acaricidal, nematicidal, fungicidal and expellant compositions.

Pyridazinone derivatives, preparation thereof, and insecticidal,

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 process for production of 2-pyrazolin-5-ones having the formula (I): ##STR1## which comprises cyclizing hydrazone derivatives having the formula (II): ##STR2## in the presence of a base; wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents a specific group; compounds having the formula (I) as well as compounds having the formula (II) and a process for production thereof.

Process for production of 2-pyrazolin-5-ones

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

Herbicidal pyrazole derivatives

Novel 3(2H)-pyridazinone derivatives having the formula I: ##STR1## wherein, R is a straight or branched C.sub.2 to C.sub.6 alkyl, R.sup.1 and R.sup.2 are each independently hydrogen or a lower alkyl, R.sup.4 is a halogen, R.sup.3 is a halogen, an alkyl, a cycloalkyl, an alkoxy, a haloalkyl, a haloalkoxy, --CN, --NO.sub.2, a phenyl, a benzyloxy, a benzyl, a phenoxy, a phenylthio, a pyridyloxy, a quinoxalyloxy, a lower alkenyloxy, a lower alkylthio, a lower haloalkylthio, --Si(CH.sub.3).sub.3, --OH, --N(CH.sub.3).sub.2, --SCN, --COOCH.sub.3 or --OCH(CH.sub.3)COOC.sub.2 H.sub.5, and n is an integer of 1 to 5, said R.sup.3 being the same or different when n is an integer of 2 to 5. A process for preparation of said derivatives is also provided. These derivatives are useful as an active ingredient of insecticidal, acaricidal, nematicidal and/or fungicidal compositions for agricultural and horticultural uses as well as of expellent compositions for ticks parasitic on animals.

Growing community of inventors

Funabashi, Japan

Masatoshi Baba