JP2021127302A - Cyclopentene compound and herbicide - Google Patents

Abstract

To provide a novel agricultural chemical, particularly a herbicide.SOLUTION: The present disclosure provides a cyclopentene compound represented by formula (1) [where A is a hydrogen atom, Z4, Z6, Z8 each denote methyl or the like, Z is Z-1 and Z-2, X1 is C1-C6 alkyl or the like] and a herbicide containing the same.SELECTED DRAWING: None

Description

The present invention relates to novel cyclopentene compounds or salts thereof, and pesticides containing cyclopentene compounds or salts thereof as active ingredients, particularly herbicides.

For example, Patent Documents 1 to 3 disclose certain cyclopentene compounds, but do not disclose any cyclopentene compound according to the present invention.

International Publication No. 96/001798 International Publication No. 98/039281 International Publication No. 2010/0818994

An object of the present invention is a highly safe active ingredient of a herbicide, which is surely effective against various weeds with a lower drug amount and alleviates problems such as soil contamination and effects on post-crops. Is to provide useful chemicals.

As a result of diligent research aimed at solving the above problems, the present inventors have found that a novel cyclopentene compound represented by the following formula (1) according to the present invention has excellent herbicidal activity as a herbicide and a target crop. The present invention has been completed by finding that it is an extremely useful compound having high safety against non-target organisms such as mammals, fish and beneficial insects and having almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.

That is, the present invention relates to the following [1] to [3].

[1]
Equation (1):

[In the formula, A represents a hydrogen atom,
Z ⁴ represents methyl or methoxy,
Z ⁶ and Z ⁸ represent methyl,
Z represents Z-1 or Z-2

t3 represents an integer of 0 or 1 and represents
t5 represents an integer of 0, 1, 2 or 3
X ¹ is a halogen atom, C _{1 to} C ₆ alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C _{1 to} C ₆ alkyl thio, C _{1 to} C ₆ alkoxycarbonyl, C (= NOR). ¹ ) Represents (C _{1- C 6} ) alkyl ^{substituted with R 2} , N (R ³ ) R ⁴ or R ^5.
R ¹ , R ² , R ³ and R ⁴ independently represent _{C 1 to} C ₆ alkyl, respectively.
R ⁵ represents C _{1 to} C ₆ alkoxy or cyano. ], A cyclopentene compound or a salt thereof.

[2]
A pesticide containing at least one selected from the cyclopentene compound according to the above [1] and a salt thereof as an active ingredient.

[3]
A herbicide containing at least one selected from the cyclopentene compound according to the above [1] and a salt thereof as an active ingredient.

The compound of the present invention has excellent herbicidal activity against various weeds and high safety against target crops, and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects, and is low. It is persistent and has a light impact on the environment.

Therefore, the present invention can provide a herbicide useful in the field of agriculture and horticulture such as paddy fields, upland fields and orchards.

Regarding the compound of the present invention represented by the formula (1), depending on the type and conditions of the substituent, the existence of a keto-enol structure tautomer represented by the following formula may be considered in some cases. Therefore, when the substituent A is introduced, B-1 is produced from the enol structure B-3 and B-2 is produced from B-4, and the present invention includes all of these structures.

The compounds included in the present invention may have E-forms and Z-form geometric isomers depending on the type of substituents, but the present invention presents these E-forms, Z-forms or E-forms. And a mixture containing the Z-form in any proportion.

In addition, the compounds included in the present invention include optically active substances due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, but the present invention includes all optically active substances or racemates. Including the body.

In addition, the compounds included in the present invention may have tautomers depending on the type of substituent, but the present invention is a mixture of all tautomers or tautomers contained in any proportion. It includes.

In addition, the compounds included in the present invention may exist as one or more rotational isomers due to limited bond rotation caused by steric hindrance between substituents, but the present invention is all. Contains a mixture of diastereomers containing the rotational isomers of the above or in any proportion.

Among the compounds included in the present invention, those which can be salted according to a conventional method are, for example, salts of hydrohalogenic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, etc. Salts of inorganic acids such as nitrate, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, formic acid, Salts of carboxylic acids such as acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartrate acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid, glutamic acid, Amino acid salts such as aspartic acid, alkali metal salts such as lithium, sodium and potassium, alkaline earth metal salts such as calcium, barium and magnesium, aluminum salts, tetramethylammonium salts, tetrabutylammonium salts and benzyltrimethylammonium salts. It can be a quaternary ammonium salt such as.

In the compound of the present invention, the N-oxide is a compound in which the nitrogen atom constituting the ring on the heterocycle is oxidized. Examples of the heterocycle capable of forming an N-oxide include a pyridine ring.

The "compound of the present invention represented by the formula (1)" is also described as the "compound of the present invention (1)", and the "compound represented by the formula (2-1)" is a "compound (2-1)". ) ”. Other compounds are similarly described in the same manner.

Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In addition, the notation of "halo" in this specification also represents these halogen atoms.

In a specific example of each substituent, "n-" means "normal", "i-" means "iso", "sec-" or "s-" means "secondary" and "tert-" or "t". -" Means" tertiary ", and Ph means phenyl.

_{The notation "C a to} C _b alkyl" in the present specification represents a linear or branched hydrocarbon group having a to b carbon atoms, for example, methyl, ethyl, n-propyl, i. Specific examples include -propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, pentyl, 1,1-dimethylpropyl, hexyl, etc., which are selected within the specified number of carbon atoms. ..

_{The notation "C a to} C _b alkoxy" in the present specification represents alkyl-O- having the above-mentioned meaning consisting of a to b carbon atoms, for example, methoxy, ethoxy, n-propyloxy, i-. Specific examples thereof include propyloxy, n-butyloxy, i-butyloxy, sec-butyloxy, tert-butyloxy, etc., and each is selected within the specified number of carbon atoms.

In the present specification, _{the notation of "halo (C a to} C _b ) alkyl" is a linear or linear structure consisting of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by a halogen atom. Represents a branched chain hydrocarbon, where the halogen atoms may be the same or different from each other when substituted by two or more halogen atoms. For example, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-Difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1, 1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2-difluoropropyl , 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1, 1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-trifluoro-1- (methyl) ethyl, 2,2,2-trifluoro-1- (trifluoromethyl) Ethyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl, 2,2,3,4,5,4-hexafluorobutyl, 2,2,3,3,4,4 Specific examples thereof include 4-heptafluorobutyl, nonafluorobutyl and the like, and each is selected within the specified number of carbon atoms.

The notation of "halo (C _{a to} C _b ) alkoxy" in the present specification represents haloalkyl-O- having the above-mentioned meaning consisting of a to b carbon atoms, for example, difluoromethoxy, trifluoromethoxy, chloro. Difluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2, -tetrafluoroethoxy, 2-chloro-1,1,2- Specific examples thereof include trifluoroethoxy, 1,1,2,3,3,3-hexafluoropropyloxy, and each is selected within the specified number of carbon atoms.

_{The notation of "C a to} C _b alkylthio" in the present specification represents alkyl-S- having the above-mentioned meaning consisting of a to b carbon atoms, for example, methylthio, ethylthio, n-propylthio, i-propylthio. , N-butylthio, i-butylthio, s-butylthio, tert-butylthio and the like are given as specific examples, and are selected within the range of each designated carbon atom number.

_{The notation of "C a to} C _b alkoxycarbonyl" in the present specification represents alkyl-OC (O) -which means that the number of carbon atoms is a to b, and for example, methoxycarbonyl or ethoxycarbonyl. , N-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl and the like as specific examples. Selected within the specified number of carbon atoms.

In the present specification, the notation of "(C _{a to} C _b ^{) alkyl substituted with R 5} " means that any hydrogen atom bonded to a carbon atom is partially or wholly represented by ^{one or more substituents R 5.} The substituted carbon atoms represent alkyl, which is the above-mentioned meaning consisting of a to b carbon atoms, and is selected in the range of each designated carbon atom number. At this time, when the substituent R ⁵ there are two or more, substituents R ⁵ may be the same or different from each other.

The term "pesticides" as used herein means insecticides / acaricides, nematodes, herbicides, fungicides and the like in the field of agriculture and horticulture.

In the present specification, the herbicide is a weed that adversely affects the growth of crops in paddy fields, upland fields, orchards, etc. It means a chemical for controlling weeds that grow randomly on non-agricultural land such as roadsides and railroad ends.

The term "weed" as used herein means a plant that naturally occurs in agricultural land such as paddy fields, upland fields, orchards, and non-agricultural land such as turflands, athletic fields, open areas, parking lots, roadsides, and railroad ends.

Paddy weeds include, for example, barnyard grass (Potamogetonaceae) weeds represented by roundleaf pondweed, Potamogeton distinctus, barnyard grass (water plantain, Alisma canaliculatum), urikawa (pygmy arrowhead, Sagittree pygmaea) and omodaka (pygmaea). Alismataceae weeds represented by Sagittaria trifolia, Azegaya (chinese sprangletop, Leptochloa chinensis), Onia Zegaya (bearded sprangletop, Leptochloa fascicularis), Barnyard grass, Echinochloa crus-galli ), Tainubier (late watergrass, Echinochloa oryzicola), Taiwan Ashikaki (southern cutgrass, Leersia hexandra), Ashikaki (Homalocenchrus japonocus) Taiwan Aiashi (saramollagrass, Ischaemum rugosum), Tsunoaiashi (itchgrass, Rottbo , Brachiaria platyphylla), Alexandergrass (Alexandergrass, Brachiaria plantaginea), Onimehishiba (large crabgrass, Digitaria sanguinalis), Tatsunotsumegaya (crowfoot grass, Dactyloctenium aegyptium), Ohishiba (goosegrass, Eleusine) Barnyard grass (bermuda grass, Cynodon dactylon), barnyard grass (fall panicum, Panicum dichoto) Gramineae weeds represented by miflorum and knotgrass, Paspalum distichum, Eleocharis kuroguwai, globe fringerush, Fimbristylis miliacea, Inu firefly (japanese bulrush, Schoenoplectus junco) juncoides), Shizui (Schoenoplectus nipponicus), Himekangarei (ricefield bulrush, Schoenoplectus mucronatus), Mizugayatsuri (Cyperus serotinus), Tamagayatsuri (smallflower umbrella sedge, Cyperus difformis), Kogomegayatsuri (rice flatsedge) Cyperus rotundus, yellow nutsedge, Cyperus esculentus, cosmopolitan bulrush, Bolboschoenus martimus, Cyperus hakonensis, etc. Weeds of the family Lemnaceae (Lemnaceae) represented by duckweed, Lemna paucicostata, etc. false pickerelweed, Monochoria korsakowii), American nutsedge (ducksalad, Heteranthera limosa), Hoteaoi (water hyacinth, Eichhornia crassipes) and nutsedge (ov) Al-leafed pondweed, Monochoria vaginalis, etc., Aeschynomene indica (Pontederiaceae) weeds, Aeschynomene indica (threestamen waterwort, Elatine triandra), etc. , Rotala indica, etc., Amaranthaceae (Lythraceae) weeds, Aeschynomene (Lidwigia epilobioides), Kidachikinbai (mexican primrose-willow, Ludwigia octovalvis), etc. junceum, Gratiola japonica, dwarf ambulia, Limnophila sessilifolia, Azena (prostrate false pimpernel, Lindernia pyxidaria), American Azena (yellowseed false pimpernel, Lindernia dubia), etc. (Indian jointvetch, Aeschynomene indica) and Amaranthaceae (Leguminosae) weeds represented by Aeschynomene indica (hemp sesbania, Sesbania exaltata), alligator weed, Alternanthera philoxeroides, etc. Amaranthaceae (Amaranthaceae) weeds, Amaranthaceae (water pepper, Polygonum hydropiper), etc. (Polygonaceae), Amaranthaceae (gooseweed, Sphenoclea zeylanica), etc. Amaranthaceae (sw Convolvulaceae weeds represented by amp morningglory, Ipomoea aquatica, Marsileaceae weeds represented by water clover, Marsilea minuta, and Devil's beggarticks, Bidens frondosa. False daisy, Eclipta prostrata), Asteraceae weeds represented by goatweed, Ageratum conyzoides and three-lobe beggarticks, Bidens tripartita.

Upland weeds include, for example, Solanaceae weeds represented by black nightshade, Solanum nigrum, jimsonweed, Datura stramonium, etc., and Granium carolinianum. Malvaceae weeds represented by Geraniaceae weeds, velvetleaf, Abutilon theophrasti and prickly sida, Sida spinosa, Malvaceae weeds, tall morning-glory, Ipomoea purpurea, USA Convolvulaceae (Convolvulaceae) weeds represented by Asagao (Ipomoea spps.) And Convolvulace (Calystegia spps.) Such as Asagao (ivyleaf morning-glory, Ipomoea hederacea) and Cohilgao (japanese bindweed, Calystegia hederacea). purple amaranth, Amaranthus lividus (redroot pigweed, Amaranthus retroflexus), Convolvulaceae (palmer amaranth, Amaranthus palmeri), Convolvulaceae (tall waterhemp, Amaranthus tuberculatus) and Amaranthus retroflexus (Amaranthus retroflexus) Amaranthaceae Weeds, Convolvulaceae (common cocklebur, Xanthium pensylvanicum), Convolvulaceae (common ragweed, Ambrosia artemisiaefolia), Convolvulaceae (giant ragweed, Ambrosia trifida), Convolvulaceae (horseweed, Conyza canadensis) pineappleweed, Matricaria ma Asteraceae (Asteraceae) represented by tricarioides, hairy galinsoga, Galinsoga ciliata, canada thistle, Cirsium arvense, common groundsel, Senecio vulgaris and annual fleabane, Erigeron annus. Weeds, Asteraceae (Brassicaceae) weeds represented by variableleaf yellowcress, Rorippa indica, wild mustard, Sinapis arvensis and shepherd's purse, Capsella Bursapastoris, oriental lady's thumb, Polygon Polygonaceae weeds represented by wild buckwheat, Polygonum convolvulus, Portulacaceae weeds represented by common purslane, Portulaca oleracea, lambsquarters, Chenopodium album, core kaza (lambsquarters, Chenopodium album) figleaved goosefoot, Chenopodium ficifolium), Russian thistle, Salsola tragus, kochia, Kochia scoparia, etc. Family (Caryophyllaceae) weeds, Asteraceae (Plantaginaceae) weeds represented by Persian speedwell (Veronica persica), etc. Family (Commelinaceae) Weeds, Hotokenoza (henbit, Lamium amplexicaule) and Himeodorikosou (purple deadnettle, Lamium purpureum), etc. And weeds of the family Euphorbiaceae represented by spotted spurge, Euphorbia maculata, etc., weeds of the family Akane family (Rubiaceae) represented by false cleavers, Galium spurium, and Asian madder, Rubia akane. , Sanshikisumire (pansy, Viola tricolor) and violet (Viola mandshurica), etc. (Fabaceae) Weeds, Papaveraceae weeds represented by filed poppy, Papaver rhoeas, and Broad- Broad- leftd weeds). Wild sorgham bicolor, fall panicum, Panicum dichotomiflorum, shuttercane, Sorgham bicolor, johnson grass, Sorghum halepense, barnyard grass, Echinochloa crus-galli var. , Barnyardgrass (cockspur grass, Echinochloa crus-galli var. horizontalis, wild oat, Avena fatua, blackgrass, Alopecurus myosuroides, windgrass, Apera spica-venti, downy brome, Bromus tectorum, italian ryegrass, Lolium multiflorum Barnyardgrass (rigid ryegrass, Lolium rigidum), barnyardgrass (littleseed canarygrass, Phalaris minor), barnyardgrass (annual bluegrass, Poa annua), barnyardgrass (goosegrass, Eleusine indica), barnyardgrasses (green foxtail, Setaria) Eleusine indica), Enocologsa (green foxtail, Setaria viridis), Aquino Enocologsa (giant foxtail, Setaria faberi) Signalgrass, Brachiaria decumbens, Poaceae weeds represented by south sandbur, Cenchrus echinatus, shortawn foxtail, Alopecurus aegualis, and purple nutsedge, Cyperus rotundus, Cyperus rotundus Typical examples include Cyperaceous weeds.

In addition, the compound of the present invention needs to control the growth of weeds such as turf, athletic field, open space, roadside, fallow in the city, and railroad end, in addition to agricultural and horticultural fields such as paddy fields, upland fields and orchards. Land or land for industrial facilities such as embankment slopes, riverbeds, road shoulders and slopes, railway floors, park green spaces, grounds, parking lots, airports, factories and storage facilities, fallows, orchards, grass It can be used in any of the treatment methods of soil treatment, soil mixing treatment and foliage treatment in land, lawn land, forestry land and the like. The weeds include horseweed (annual bluegrass, Poa annua), horseweed (dandelion, Taraxacum officinale), erigeron bonarien (hairy fleabane, Conyza bonariensis), and erigeron bonarien (guernsey). Conyza sumatrensis, horseweed, conyza canadensis, wavy bittercress, cardamine flexuosa, white clover, trifolium repens, lawn pennywort, hydrocotyle sibthorpioides Green kyllinga, Cyperus brevifolius, Kyllinga brevifolia), Sugina (field horsetail, Equisetum arvense) and the like.

The crops in the present specification include field crops or paddy crops, garden crops, turf, fruit trees, etc., and specifically, for example, corn, rice, wheat, barley, lime tree, embaku, sorghum, cotton, soybean, peanut. , Soba, Tensai, Beet, Rapeseed, Sunflower, Sugar cane, Tobacco and other agricultural products; , Abrana vegetables (Daikon, Cub, Seiyouwasabi, Korurabi, Hakusai, Cabbage, Karashina, Broccoli, Califlower, etc.), Kiku vegetables (Gobo, Shungiku, Artichoke, Lettuce, etc.) Asparagus), vegetables of the family Seri (carrots, parsley, celery, American bows, etc.), vegetables of the family Akaza (sourensou, fudansou, etc.), vegetables of the family Sesos (siso, mint, basil, etc.), strawberries, sweet potatoes, yamanoimo, and sweet potatoes, etc. Vegetables: Fruits (apple, pear, Japanese pear, karin, marumero, etc.), nuclear fruits (peach, sumomo, nectarin, seaweed, sweet potato, apricot, prun, etc.), citrus fruits (unshu mikan, orange, lemon, lime, etc.) Grapefruit, etc.), Hard fruits (Kuri, walnut, Hashibami, Almond, Pistachio, Cashew nuts, Macadamia nuts, etc.), Liquid fruits (Blueberries, Cranberries, Blackberries, Raspberries, etc.), Grape, oysters, Olives, Biwa, Bananas, Coffee , Vegetables such as nut palm, coco palm and abra palm; cha, mulberry, street tree (toneriko, kabanoki, hanamizuki, eucalyptus, ginkgo, lilac, maple, oak, poplar, hanazuou, fu, platanas, zelkova, kurobe, mominoki, tsuga, Trees other than fruit trees such as rats, pine, touhi, ichii, nire, tochinoki, coral, inumaki, sugi, hinoki, croton, masaki, kanamechi, etc .; ), Bentgrass (Konukagusa, Hikonukagusa, Itokonu Kagusa, etc.), Bluegrass (Nagahagusa, Oosuzumenokatabira, etc.), Fesks (Oniushinokegusa, Itoshinokegusa, Hiushinokegusa, etc.), Ryegrass (rat, moth, etc.) Lawns such as Oawagaeri; Oil crops such as oil palm and Nanyouabragiri; Vegetables ( Rose, carnation, kiku, gypsophila, gypsophila, gerbera, marigold, salvia, petunia, barbena, tulip, aster, lindow, lily, pansy, cyclamen, orchid, tin orchid, lavender, stock, kale, primula, poinsettia, gradialus, cattleya , Daisy, verbena, symbidium, begonia, etc.); foliage plants, etc., but are not limited to these.

Furthermore, HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapill and thifensulfuronmethyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, and acetyl CoA carboxylase inhibitors such as setoxydim Also included are agricultural and horticultural plants that have been granted resistance to PPO inhibitors such as flumioxazine, herbicides such as bromoxinyl, dicamba and 2,4-D by classical breeding methods and genetic recombination techniques.

Examples of agricultural and horticultural plants that have been endowed with resistance by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill. It is already sold under the product name.

Similarly, there are soybeans resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods, which are already sold under the trade name of STS soybeans. Similarly, SR corn and the like are examples of agricultural and horticultural plants in which resistance to acetyl-CoA carboxylase inhibitors such as trionoxime-based and aryloxyphenoxypropionic acid-based herbicides has been imparted by classical breeding methods. Agricultural and horticultural plants resistant to acetyl-CoA carboxylase inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad). .Sci.USA) Vol. 87, pp. 7175-7179 (1990), etc. In addition, mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005). A plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing it into a plant or by introducing a mutation related to resistance imparting into a crop acetyl-CoA carboxylase. Furthermore, a base substitution mutation-introduced nucleic acid represented by Chimera Plasty Technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) is introduced into plant cells to produce crops (acetyl-CoA carboxylase / herbicide). By inducing site-specific amino acid substitution mutations in the target) gene, plants resistant to acetyl-CoA carboxylase inhibitors / herbicides can be created.

Examples of agricultural and horticultural plants that have been imparted resistance by gene recombination technology include glyphosate-tolerant corn, soybean, cotton, rapeseed, and tensai varieties, RoundupReady (trade name), and Agrisure GT (trade name). It is already sold under product names such as AgrisureGT) (product name). Similarly, there are glufosinate-resistant corn, soybean, cotton, and rapeseed varieties that are genetically modified, and are already sold under trade names such as LibertyLink (trade name). Similarly, bromoxynil-resistant cotton produced by genetic recombination technology is already sold under the trade name of BXN.

The above-mentioned agricultural and horticultural plants also include plants capable of synthesizing, for example, selective toxins known in the genus Bacillus by using genetic recombination technology.

Examples of the insecticidal toxin expressed in such a recombinant plant include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab derived from Bacillus thuringiensis. , Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxins, VIP1, VIP2, VIP3 or VIP3A and other insecticidal proteins; nematode-derived insecticidal proteins; Toxins produced by animals such as insect-specific neurotoxins; Streptococcal toxins; Plant lectins; Aglutinin; Protein inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; lysine, corn- Ribosome-inactivating proteins (RIP) such as RIP, abrin, saporin, briozin; steroid-metabolizing enzymes such as 3-hydroxysteroid oxidase, exdisteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdison inhibitor; HMG-CoA reductase; Ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; immature hormone esterases; diuretic hormone receptors; stillben synthase; bibenzyl synthase; chitinase; glucanase and the like.

In addition, as toxins expressed in such transgenic plants, δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, and insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A. Includes hybrid toxins, partially deficient toxins, and modified toxins. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology. As a toxin that is partially deficient, Cry1Ab, which is partially deficient in the amino acid sequence, is known. As the modified toxin, one or more of the amino acids of the natural toxin have been replaced.

Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, European Patent Application Publication No. 0374753, International Publication No. 93/07278, International Publication No. 95/34656, European Patent Application Publication No. It is described in patent documents such as 0427529, European Patent Application Publication No. 451878, and International Publication No. 03/052073. The toxins contained in these recombinant plants confer resistance to Coleoptera pests, Diptera pests, and Lepidopteran pests, in particular.

Also, transgenic plants containing one or more insecticidal pest resistance genes and expressing one or more toxins are already known, and some are commercially available. Examples of these genetically modified plants include YieldGard (trade name) (corn variety expressing Cry1Ab toxin), YieldGard Rootworm (trade name) (corn variety expressing Cry3Bb1 toxin), YieldGard Plus (trade name) (corn variety expressing Cry1Ab and Cry3Bb1 toxins), Herculex I (trade name) (phosphino for conferring resistance to Cry1Fa2 toxin and gluhosinate) Tricin N-acetyltransferase (PAT) -expressing corn varieties), NuCOTN33B (trade name) (Cry1Ac toxin-expressing cotton varieties), Bollgard I (trade name) (Cry1Ac toxin-expressing cotton varieties), Bollgard II (trade name) (Cry1Ac and Cry2Ab toxin-expressing cotton varieties), VIPCOT (trade name) (VIP toxin-expressing cotton varieties), NewLeaf (trade name) (Cry3A toxin) Expressed potato varieties), Nature Guard Agrisure GT Advantage (NatureGard (trade name) Agrisure (trade name) GT Advantage) (GA21 glyphosate resistance trait), Agrisure CB Advantage (Agrisure (trade name) CB Advantage) (Bt11 corn bowler) (CB) trait), protecta (Protecta) (trade name) and the like.

The crops also include those that have been endowed with the ability to produce antipathogenic substances with selective action using genetic recombination techniques.

Anti-pathogenic substances include, for example, PR proteins (PRPs: described in European Patent Application Publication No. 0392225); sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses). Ion channel inhibitors such as (known); stillben synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, antibiotics with heterocycles, protein factors involved in plant disease resistance (plant disease resistance) Examples include substances produced by microorganisms such as (called genes and described in International Publication No. 03/000906). Such antipathogenic substances and genetically modified plants that produce them are described in European Patent Application Publication No. 0392225, International Publication No. 95/33818, European Patent Application Publication No. 0353191, etc. ing.

The above-mentioned crops also include crops to which useful traits such as oil component modification and amino acid content enhancing traits have been imparted by using gene recombination technology. Examples include VISTIVE (trade name) (low-linolenic soybean with reduced linolenic content), high-lysine (hig hoil) corn (corn with increased lysine or oil content), and the like.

Furthermore, a plurality of useful traits such as the above-mentioned classical herbicide traits or herbicide resistance genes, insecticidal pest resistance genes, antipathogenic substance production genes, oil component modification and amino acid content enhancing traits are described. Combined stack varieties are also included.

The compound of the present invention represented by the formula (1) can be produced, for example, by the following method.

Manufacturing method 1
The compound (1) of the present invention can be produced, for example, by reacting the compound (2-1) with the compound (51).

(In the formula, Z ⁴ , Z ⁶ , Z ⁸ and Z have the same meanings as described above.)
Compound (1) can be produced by reacting compound (2-1) with compound (51) in the presence of Lewis acid in a solvent or in the absence of a solvent.

Examples of the acid used include Lewis acids such as boron trifluoride-ethyl ether complex.

The equivalent amount of acid used can be in the range of 0.01 to 10 equivalents with respect to 1 equivalent of compound (2-1), preferably in the range of 0.05 to 5 equivalents.

The equivalent of compound (51) to be used can be in the range of 0.5 to 50 equivalents with respect to 1 equivalent of compound (2-1), preferably in the range of 1 to 20 equivalents.

Some of the compound (51) are known compounds, and some are commercially available.

Some of the compounds (2-1) are known compounds, and some are commercially available. Others can also be produced according to a known method described in the literature, for example, International Publication No. 2016/098899.

When a solvent is used, the solvent used may be any as long as it is inert to the reaction, and examples thereof include ethers such as tetrahydrofuran and halogenated hydrocarbons such as dichloromethane.

The reaction temperature can be set at any temperature from −80 ° C. to the reflux temperature of the reaction mixture, preferably in the range of 0 ° C. to the reflux temperature of the reaction mixture.

The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually set arbitrarily in the range of 5 minutes to 100 hours, preferably in the range of 1 hour to 48 hours.

In the production method 1, if necessary, it may be carried out in an atmosphere of an inert gas such as nitrogen or argon.

In the production method 1, the reaction mixture after completion of the reaction is subjected to usual post-treatment such as direct concentration or dissolution in an organic solvent, washing with water and concentration, or putting into ice water, and concentration after extraction of the organic solvent. Can be obtained. When the need for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, and liquid chromatograph sorting.

The compound of the present invention can be used as a herbicide for paddy fields in any of the treatment methods of soil treatment and foliage treatment under flooding.

In addition, the compound of the present invention can be used as a herbicide for upland fields and orchards in any of the treatment methods of soil treatment, soil mixing treatment and foliage treatment.

In addition, the compound of the present invention needs to control the growth of weeds such as turf, athletic field, open space, roadside, fallow in the city, and railroad end, in addition to agricultural and horticultural fields such as paddy fields, upland fields and orchards. Land or land for industrial facilities such as embankment slopes, riverbeds, road shoulders and slopes, railway floors, park green spaces, grounds, parking lots, airports, factories and storage facilities, fallows, orchards, grass It can be used in any of the treatment methods of soil treatment, soil mixing treatment and foliage treatment in land, lawn land, forestry land and the like.

When the compound of the present invention is applied as a herbicide, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrant, a spreading agent, a thickener, an antifreeze agent, a binder, and a solid. Add a binder, a disintegrant, a decomposition inhibitor, etc., and use it as a formulation of any dosage form such as a wettable powder, an emulsion, a flowable agent, a dry flowable agent, a liquid agent, a powder, a granule, or a gel agent. be able to. Further, from the viewpoint of labor saving and safety improvement, the above-mentioned preparation of any dosage form can be encapsulated in a water-soluble package and provided.

Examples of the solid carrier include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acidic clay, attapulsite, zeolite and diatomaceous earth, and inorganic substances such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicate.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as γ-butyrolactone. Examples include acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.

These solid and liquid carriers may be used alone or in combination of two or more.

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan. Nonionic surfactants such as fatty acid esters, alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, Anionic surfactants such as salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates and polystyrene sulfonates, Examples thereof include cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, and amphoteric surfactants such as amino acid type and betaine type.

The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by mass with respect to 100 parts by mass of the pharmaceutical product of the present invention. In addition, these surfactants may be used alone or in combination of two or more.

The compound of the present invention may be mixed and applied with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of preparation or spraying, if necessary.

In particular, by applying the mixture with other herbicides, it is expected that the cost can be reduced by reducing the amount of the applied drug, the herbicide spectrum can be expanded by the synergistic action of the mixed agents, and a higher herbicide effect can be expected. At this time, it is possible to combine with a plurality of known herbicides at the same time.

The amount of the compound of the present invention to be applied varies depending on the application situation, application time, application method, cultivated crop, etc., but generally, the amount of the active ingredient is appropriately about 0.005 to 50 kg per hectare (ha).

Next, a compounding example of the pharmaceutical product when the compound of the present invention is used is shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by mass.
Wettable powder 0.1 to 80 parts of the present invention Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Other examples include anti-caking agents and anti-decomposition agents.
Emulsion Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Other examples include spreading agents and decomposition inhibitors.
Flowable agent 0.1 to 70 parts of the compound of the present invention Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Other examples include antifreeze agents and thickeners. Be done.
Dry flowable agent 0.1 to 90 parts of the compound of the present invention Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, a binder, a decomposition inhibitor and the like. ..
Liquids Compounds of the present invention 0.01 to 70 parts Liquid carriers 20 to 99.99 parts Others 0 to 10 parts Other examples include antifreeze agents and spreading agents.
Granules 0.01 to 80 parts of the compound of the present invention Solid carrier 10 to 99.99 parts Others 0 to 10 parts Other examples include binders, decomposition inhibitors and the like.
Powders Compounds of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 10 parts Other examples include anti-drift agents and anti-decomposition agents.

When using, the above-mentioned preparation is sprayed as it is or diluted 1 to 10,000 times with water.

Examples of preparations Next, examples of pesticide preparations containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited to these. In the following formulation examples, "parts" means parts by mass.
[Formulation Example 1] Wettable compound No. 1 of the present invention. 1-001 20 parts Pyrophyllite 76 parts Solpole 5039 2 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
Carplex # 80 Part 2 (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
The above is uniformly mixed and pulverized to obtain a wettable powder.
[Formulation Example 2] Emulsion Compound No. 2 of the present invention. 1-001 5 parts xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.
[Formulation Example 3] Flowable agent Compound No. 3 of the present invention. 1-001 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name)
Lunox 1000C 0.5 part (anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
After uniformly mixing 0.02 parts of xanthan gum and 64.48 parts of water or more, wet pulverization is performed to obtain a flowable agent.
[Formulation Example 4] Dry flowable agent Compound No. 4 of the present invention. 1-001 75 parts High Tenor NE-15 5 parts (Anionic surfactant: Dai-ichi Kogyo Seiyaku Co., Ltd. trade name)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries, Ltd. trade name)
Carplex # 80 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and crushing the above, a small amount of water is added, stirred and mixed and kneaded, granulated by an extrusion type granulator, and dried to obtain a dry flowable agent.
[Formulation Example 5] Granules Compound No. 5 of the present invention. 1-001 1 part Bentonite 55 parts Talc 44 parts After uniformly mixing and crushing, add a small amount of water, stir and mix and knead, granulate with an extrusion type granulator, and dry to make granules.

The compound of the present invention may be mixed and applied with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of preparation or spraying, if necessary.

In particular, by applying the mixture with other herbicides, it is expected that the cost can be reduced by reducing the amount of the applied drug, the herbicide spectrum can be expanded by the synergistic action of the mixed agents, and a higher herbicide effect can be expected. At this time, it is possible to combine with a plurality of known herbicides at the same time.

Preferred herbicides for mixed use with the compounds of the present invention include, for example, 4-CPA (4-CPA), 4-CPA salts (4-CPA-salts), 4-CPB (4-CPB), 4 -CPP (4-CPP), 2,4-D (2,4-D, 2,4-PA), 2,4-D salts (2,4-D-salts), 2,4-D Salts of esters (2,4-D-esters), 3,4-DA (3,4-DA), 2,4-DB (2,4-DB), 2,4-DB (2,4-DB) -salts), 2,4-DB ester (2,4-DB-esters), 3,4-DB (3,4-DB), 2,4-DEB (2,4-DEB), 2,4 -DEP (2,4-DEP), 3,4-DP (3,4-DP), 2,4,5-T (2,4,5-T), 2,4,5-T salts ( 2,4,5-T-salts), 2,4,5-T esters (2,4,5-T-esters), 2,4,5-TB (2,4,5-TB), 2 , 3,6-TBA (2,3,6-TBA, TCBA), 2,3,6-TBA salt (2,3,6-TBA-salts), acetochlor, acifluorfen ), Acifluorfen-methyl, acifluorfen-sodium, aclonifen, acrolein, alachlor, allidochlor, CDAA, alloxydim, Aloxydim-sodium, alloxydim-sodium, allyl alchol, alorac, ametridione, ametryn, ambuzin, amiclabazone, amidochlor, amidosulfron (Amidosulfuron), aminocyclopyrachlor, aminocyclopyrachlor-methyl, aminocyclopyrachlor-potassium, aminopyralid, salt of aminopyralid (Aminopyralid-salts), amiprophos, amiprophos-methyl, amitrole, aminotriazole, ATA, ammonium sulfamate, AMS, anilofos, anisuron, Ashlam, ashlam salt (asulam-salts), atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, azyprotryn, barban, CBN, BCPC (BCPC), beflubutamid, beflubutamid-M, beflubutamid-M, benazolin, benazolin-ethyl, benazolin-salts, bencarbazone, bencarbazone, benfluralin, benfluralin , Benfuresate, bensulfuron, bensulfuron-methyl, bensulide, SAP, bentazon, bentazone, bentazone-sodium, bentranil, benzadox (Benzadox), benzadox-ammonium, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop , Benzoylprop-ethyl, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bialaphos, bilanafosatriu Calcium cyanamide, binapacryl, bispyribac, bispyribac-sodium, bixlozone, borax, bromacil, bromacil-salts , Bromobonil, bromobutide, bromofenoxim, bromopyrazon, bromoxynil, bromoxynil-potassium, bromoxynil-esters, butachlor ), Butafenacil, butamifos, butenachlor, butralin, butraline, buthidazole, buthiuron, butroxydim, buturon, butyrate, butyrate (Cafenstrole), calcium cyanamide, cambendichlor, calcium chlorate, carbasulam, carbetamide, carboxazole, carfentrazone , Carfentrazone-ethyl, CDEA (CDEA), CEPC (CEPC), chlomethoxyfen, chlomethoxynil, chloramben, chloramben-salts, chloramben methyl (chloramben-salts) chloramben-methyl, chloramben-methylammonium, chloranocryl, dicryl, chlorazifop, chlorazihop propargyl (chlor) azifop-propargyl, chlorazine, chlorbromuron, chlorbufam, BIPC, chloreturon, chlorfenac, fenac, chlorfenac-salts, chlor. Fenprop (chlorfenprop), chlorfenprop-methyl, chlorflurazole, chlorflurenol, chlorflurenol-methyl, chloridazon, PAC, pyrazon (Chlorimuron), chlorimuron-ethyl, chlornidine, chlornitrofen, CNP, chloroacetic acid, monochloroacetic acid, sodium chloroacetate (SMA), chlorotoluron. , Chloroxuron, chloroxynil, chlorprocarb, chlorphtalim, chlorpropham, IPC, chlorsulfuron, chlorthal, TCTP, chlortal ester (chlorthal, TCTP) chlorthal-esters, chlorthiamid, DCBN, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clacyfos, clethodim, cliodinate, cliodinate (Clodinafop), clodinafop-propargyl, clodinafop (clofop), clodinafisobutyl (clofop-isobut) yl), clomazone, clomeprop, cloprop, cloproxydim, clopyralid, clopyralid-methyl, clopyralid-salts, chloranthrum (clopyralid-salts) cloransulam), cloransulam-methyl, copper sulfate (divalent) (copper sulfate), CPMF (CPMF), CPPC (CPPC), credazine, cresol, cumyluron, cyanatrin (Cyanatryn), cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, COMU ), Cyhalofop, cyhalofop-butyl, cyperquat, cyperquat-chloride, cyprazine, cyprazole, cypromid, daimuron , Dymron, dalapon, salt of dalapon (dalapon-salts), dazomet, sodium dazomet-sodium, delacrol, desmedipham, desmetryn, dialate (dazomet) di-allate, dicamba, MDBA, dicamba-salts, dicamba-esters, dichlobenil (DBN), dichloraurea, DCU, dichlormate, ortho Dichlorobenzene (DCB), dichloroprop (dichl) orprop), dichlorprop-salts, dichlorprop-esters, dichlorprop-P, dichlorprop-P-salts, dichlorprop-P-salts Chlorprop-P ester (dichlorprop-P-esters), dichlorofop, diclohop-methyl, diclohop-P, dichlorofop-P-methyl, diclosulam , Diethamquat, diethamquat dichloride, diethatyl, diethatyl-ethyl, difenopenten, difenopenten-ethyl, difenoxuron , Difenzoquat, difenzoquat metilsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, diflufenzopyr-sodium, dimefuron, dimepiperate ), Dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-p, dimethenamid-p, dimexano, dimidazon, dimethyl disulfide, dimethyl disulfide. Dinitramine, dinophenate, dinoprop, dinosam, dinoseb, DNBP, dinoseb-salts, dinoseb-esters, dinoterb, dinoterb, dinoterb, dinoterb, DNBP Dinoseb salt (dinoterb-sa) lts, dinoterb-esters, diphenamid, dipropalin, dipropetryn, diquqt, diquqt dibromide, disul, 2,4-PS , Disul-sodium, dithiopyr, diuron, DCMU, DMPA (DMPA), DNOC (DNOC), DNOC salts (DNOC-salts), EBEP (EBEP), eglinazine , Eglinazine-ethyl, endothal, endothal-salts, epronaz, EPTC (EPTC), erbon, esprocarb, ethachlor ), Ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, etaprochlor, ethidimuron, ethiolate, ethiozin, etohet. ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD (EXD), fenasulam, Fenoprop (fenoprop, 2,4,5-TP, silvex), Fenoprop-salts, Fenoprop-esters, fenoxaprop, fenoxaprop- Ethyl), fenoxaprop-p, fenoxaprop-p-ethyl, fenoxasulfo ne, fenquinotrione, fenteracol, fenthiaprop, fenthiaprop-ethyl, fentrazamide, ferrous ester, phenurone (Fenuron), Fenuron TCA (fenuron-TCA), flamprop (flamprop), flamprop-esters, flamprop-M, flamprop-M-esters, Flazasulfuron, florasumam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-esters, fluazifop- P), fluazifop-p-esters, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, fluphenylaset (Flufenacet), flufenican, flufenpyr, flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac, flumiclorac-pentyl , Flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, fluoromidine, fluoronitrophen (fluoromidine) flu oronitrofen, CFNP), fluothiuron, flupoxam, flupropacil, flupropanate, tetrapion, flupropanate-sodium, flupyrsulfuron, flupyrsulfuron methyl (Flupyrsulfuron-methyl), flupyrsulfuron-sodium, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, ester of fluroxypyr (fluroxypyr) fluroxypyr-esters, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine ), Fosamine-ammonium, furyloxyfen, glufosinate, glufosinate-salts, glufosinate-P, glufosinate-P-salts ), Glyphosate, Glyphosate-salts, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxydine, haloxyfop, haloxyfop-sodium, haloxyfop-esters, haloxyfop-P , Haloxyfop-p-esters, herbimycin, hexachloroacetone, HCA, hexazinone, imazamethabenz, imazamethabenz-methyl, imazamethabenz-methyl (imazamethabenz-methyl) imazamox), imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquinmethyl (Imazaquin-methyl), imazaquin-salts, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indaziflam Iodosulfuron, iodosulfuron-sodium, iodosulfuron-methyl, iodosulfuron-methyl-sodium, iofensulfuron, yofensulfuron Sodium (iofensulfuron-sodium), ioxynil, ioxynil-salts, ioxynil-esters, ipazine, ipfencarbazone, iprymidam, isocarbamide (Isocarbamid), isocil, isoprocil, isomethiozin, isonoluron, isopolinate, isopropalin, isoproturon (Isoproturon), isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, Ketospiradox-potassium, lactofen, lancotrione, lancotrione-sodium, lenacil, linuron, MCPA (MCPA), MCPA salts (MCPA) -salts), MCPA Esters (MCPA-esters), MCPB (MCPB), MCPB Salts (MCPB-salts), MCPB Esters (MCPB-esters), Mecoprop, MCPP, Mecoprop-salts ), Mecoprop-esters, Mecoprop-P, Mecoprop P salt (mecoprop-P-salts), Mecoprop P ester (mecoprop-P-esters), Medinoterb, Medino Terbuacetate (medinoterb actate), mefenacet, mefluidide, mefluidide-salts, mesoprazine, mesosulfuron, mesosulfuron-methyl, mesosulfuron-methyl, mesosulfuron-methyl Metam, carbam, metam-salts, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, metabenzthiazuron, methibenzuron), metalpropalin (methalpropalin), metazol (methaz) ole, methiobencarb, methiuron, methometon, methoprotryne, methoprotryn, methoxyphenone, methiopyrisulfuron, methiopyrisulfuron, methiozolin, methyl azide , Methyl bromide, methyl dymron, methyl iodide, methyl isothiocyanate, metobenzuron, metobromuron, metolachlor, S S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monalide, monalide ), Monolinuron, monosulfuron, monosulfuron-methyl, monuron, CMU, monuron-TCA, morfamquat, morfamquat dichloride. ), Naproanilide, napropamide, napropamide-M, naptalam, NPA, naptalam-sodium, neburon, nicosulfuron, nipyraclofen ), Nitralin, nitrofen, NIP, niclofen, nitrofluorfen, norflurazon, noru ron, norea, OCH (OCH), oleic acid, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, Oxapyrazine salts (oxapyrazon-salts), oxasulfuron, oxaziclomefone, oxyfluorfen, parafluron, paraquat, paraquat dichloride, paraquat dimethylsulfate. dimetilsulfate, pebulate, pelargonic acid, nonanoic acid, pendimethalin, penoxsulam, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenol lau Rate (pentachlorophenyl laurate), pentanochlor (solan, CMMP), pentoxazone (pentoxazone), perfluidone, petoxamide (pethoxamid), phenisopham, phenmedipham, phenmedipham ethyl (phenmedipham) -ethyl, phenobenzuron, picloram, picloram-salts, picloram-esters, picolinafen, pinoxaden, piperophos, hydrangea Potassium azide, potassium cyanate, pretilachlor, pr imisulfuron, primisulfuron-methyl, propyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, proglinazine ethyl (Proglinazine-ethyl), prometon, prometryn, prometryne, propachlor, propanil, DCPA, propaquizafop, propazine, propham, propiso Propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, pronamide, prosulfalin, prosulfocarb, Prosulfuron, proxan, IPX, proxan-sodium, prynachlor, pydanon, pyraclonil, pyraflufen, pyraflufen- Ethyl, pyrasulfotole, pyrazolynate, pyrazolate, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyrivanbenz-isopropyl, pyrivanbenz Propyl (pyribambenz-propyl), pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridi Pyridate, pyriftalid, pyriminob
ac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinchlorac quinclorac, quinclorac-dimethylammonium, quinclorac-methyl, quinmerac, quinoclamine, ACN, quinonamid, quizalofop, quizalofop ester -esters, quizalofop-P, quizalofop-P-esters, rhodethanil, rimsulfuron, saflufenacil, sebuthylazine, secbmethon Sethoxydim, siduron, simazine, CAT, simeton, simetryn, simetryne, sodium azide, sodium chlorate, sulcotrione , Sulfallate, CDEC, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, sulforic acid, sulglycapin, sweep (Swep, MCC), tabron, TCA (TCA, trichloroacetic acid), TCA salt (TCA-salts), TCA esteryl (TCA-ethadyl), tebutam, butam, tebuthiuron, Tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbutol, MPMC, terbuchlor, terbumeton, terbuthylazine, terbuthylazine (Terbutryn), tetflupyrolimet, tetrafluron, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazimin, thidiazuron, thiencarbazone Methyl (thiencarbazone-methyl), thifensulfuron, thifensulfuron-methyl, thiobencarb, benthiocarb, tiafenacil, tiocarbazil, tioclorim, tolpyralate ), Topramezone, tralkoxydim, triafamone, triallate, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron -methyl, tricamba, triclopyr, triclopyr salts (triclopyr-salts), triclopyr esters, tridiphane, trietazine, trifloxysulfuron ), Trifloxysulfuron-sodium, trifludimoxazin, tri Trifluralin, triflusulfuron, triflusulfuron-methyl, trifop, trifop-methyl, trifopsime, trihydroxytriazine, cyanuric acid , Trimeturon, tripropindan, tritac, tritosulfuron, vernolate, xylachlor, 6-{(difluoromethyl) thio} -N2, N4 -Diisopropyl-1,3,5-triazine-2,4-diamine (CAS 103427-73-2), (R) -2-[{7- (2-chloro-4- (trifluoromethyl) phenoxy) naphthalene -2-yl} oxy] Methyl propanoate (CAS 103055-25-0), Propan-2-one O- (12H-dibenzo [d, g] [1,3] dioxosin-6-carbonyl) oxime (CAS 503819) -68-9), [{(2- (N-methylmethylsulfonamide) -2-oxoethyl) amino} methyl] phosphonic acid (CAS 98565-18-5), 2-[{2- (4-(((() 6-Chloroquinoxalin-2-yl) oxy) phenoxy) propanoyl} oxy] -3-methyl-3-butenoate (CAS 1191932-79-2), 2- (3,7-dichloroquinolin-8-carbonyl) -3-Hydroxy-2-cyclohexene-1-one (CAS 1350901-36-8), O- (2,4-dimethyl-6-nitrophenyl) O-methylisopropylphosphoramidothioate (CAS 189517-75-7) ), 5- [N-{(4,6-dimethylpyrimidine-2-yl) carbamoyl} sulfamoyl] -1- (pyridin-2-yl) -1H-pyrazol-4-carboxylate (CAS 104770-29-) 8), 4- [2-Chloro-3-{(3,5-dimethyl-1H-pyrazol-1-yl) methyl} -4- (methylsulfonyl) benzoyl] -1,3-dimethyl-1H-pyrazol- 5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate (CAS) 1911613-97-2), 4- [2-Chloro-4- (methylsulfonyl) -3-{(2,2,2-trifluoroethoxy) methyl} benzoyl] -1-ethyl-1H-pyrazol-5- Il 1,3-dimethyl-1H-pyrazole-4-carboxylate (CAS 1992017-55-6), 1- {2-chloro-3- (3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazole) -4-carbonyl) -6- (trifluoromethyl) phenyl} piperidine-2-one (CAS 1855929-45-1), 1,3-dimethyl-4- {2- (methylsulfonyl) -4- (trifluoro) Methyl) benzoyl} -1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazol-4-carboxylate (CAS 1622908-18-2), 2-[{3- (2-chloro-4-fluoro-) 5- (3-Methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidine-1 (2H) -yl) phenoxy) pyridin-2-yl} oxy] ethyl acetate (CAS 353292) -31-6), 2-Methyl-N- (5-Methyl-1,3,4-oxadiazol-2-yl) -3- (Methylsulfonyl) -4- (Trifluoromethyl) benzamide (CAS 1400904) -50-8), 2-chloro-N- (1-methyl-1H-tetrazole-5-yl) -3- (methylthio) -4- (trifluoromethyl) benzamide (CAS 1361139-71-0), 2 -Chloro-N- (1-methyl-1H-tetrazole-5-yl) -3- (methylsulfonyl) -4- (trifluoromethyl) benzamide (CAS 1361139-73-2), 4- (4-fluorophenyl) ) -6- (2-Hydroxy-6-oxo-1-cyclohexene-1-carbonyl) -2-methyl-1,2,4-triazine-3,5 (2H, 4H) -dione (CAS 1353870-34-) 4), 4-Amino-3-chloro-5-fluoro-6- (7-fluoro-1H-indol-6-yl) picolinic acid (CAS 1628702-28-2), 2- (3,4-dimethoxyphenyl) ) -4- (2-Hydroxy-6-oxocyclo-1-hexene-1-carbonyl) -6-methylpyridazine-3 (2H) -one (CAS 2138855-12-4), 3- (2,6-dimethyl) Phenyl) -6- (2-hydroxy-6-o) Xocyclo-1-hexene-1-carbonyl) -1-methylquinazoline-2,4 (1H, 3H) -dione (CAS 1639426-14-4), F4050 (test name), F9960 (test name), OK-701 (Test name), SL-1201 (test name) and the like can be mentioned. These components can be used alone or in combination of two or more, and the ratio when mixed can be freely selected.

Examples of the drug damage reducing agent include benoxacor, BPCMS (BPCMS, CSB), cloquintocet, cloquintocet-mexyl, cumyluron, cyometrinil, and cyprosul. Cyprosulfamide, daimuron, dymron, dichlormid, dicyclonon, diclonon, dietholate, dimepiperate, disulphoton, fenchlorazole, fenchlorazole. Ethyl (fenchlorazole-ethyl), fenclorim, flurazole, fluxofenim, furilazole, hexim, isoxadifen, isoxadifen-ethyl, MCPA ( MCPA), mecoprop, mefenpyr, mefenpyr-diethyl, mephenate, metcamifen, methoxyphenone, 1,8-naphthalic anhydride , NA), octamethylene-diamine, oxabetrinil, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (AD67, MON4660), 4-carboxy-3, 4-Dihydro-2H-1-benzopyran-4-acetic acid (CL304415), 2,2-dichloro-N- [2-oxo-2- (propenylamino) ethyl] -N-2-propenylacetamide (DKA-24) , 2- (Dichloromethyl) -2-methyl-1,3-dioxolane (MG191), 2-propenyl 1-oxa-4-azaspiro [4,5] decane-4-carbodithioate (MG838), (3- Dichloroacetyl-5- (2-furyl) -2,2 -Dichlorooxalidine) (MON13900), (N-allyl-N-[(1,3-dioxolane-2-yl) methyl] dichloroacetamide (PPG-1292), 3- (dichloroacetyl) -2,2- Examples thereof include dimethyl-1,3-oxazolidine (R28725), 3- (dichloroacetyl) -2,2,5-trimethyl-1,3-oxazolidine (R29148) and 1-dichloroacetyl azepan (TI-35). .. These components can be used alone or in combination of two or more, and the ratio when mixed can be freely selected.

Hereinafter, the present invention will be described in more detail by specifically describing synthetic examples and test examples of the cyclopentene compound represented by the formula (1) used as the active ingredient in the herbicide of the present invention as examples. The present invention is not limited thereto.

[Synthesis example]
For the medium pressure preparative liquid chromatography described in the following synthesis example, a medium pressure preparative device manufactured by Yamazen Co., Ltd .; YFLC-Wprep (flow velocity 18 ml / min, silica gel 40 μm column) was used.

The proton nuclear magnetic resonance chemical shift values of example, using _Me 4 Si (tetramethylsilane) as the reference substance, was measured at 300 MHz. Moreover, the solvent used for the measurement is described in the following synthesis example. The symbols in the proton nuclear magnetic resonance chemical shift values of the examples have the following meanings.
s: singlet, brs: broad singlet, m: multiplet Synthesis example 1: 5- (2,4-dimethoxyphenyl) -3-hydroxy-2- (2-methoxy-4,6-dimethylphenyl) cyclopent-2- Synthesis of En-1-one (Compound No. 1-001 of the present invention) 2- (2-Methoxy-4,6-dimethylphenyl) cyclopent-4-ene-1,3-dione 460 mg, 1,3-dimethoxybenzene To a mixed solution of 276 mg and 10 ml of dichloromethane was added 0.26 ml of the borontrifluoride-ethyl ether complex at room temperature. After completion of the addition, the mixture was stirred at room temperature for 21 hours. After completion of the reaction, 3 ml of a 1 mol / L hydrochloric acid aqueous solution and 3 ml of a saturated brine were added to the reaction mixture, and the mixture was extracted with chloroform (5 ml × 1). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 70: 0 to 0: 100 (volume ratio, the same applies hereinafter)) to obtain 88 mg of the desired product. Obtained as a white solid.

The compound of the present invention can be synthesized according to the above-mentioned production method and Examples. Table 1 shows examples of the compound of the present invention produced in the same manner as in Synthesis Example 1.

In the table, the description of "Me" is methyl, the description of "Et" is ethyl, the description of "n-Pr" is normal propyl, the description of "i-Pr" is isopropyl, and the description of "=" is. Represents each double bond.

In the table, the description of Z-1 and Z-2 represents the following structure.

Number described in the above structural formula is intended to represent the substitution position of the substituents ^{X 1,} for example, in the table, the description "Z-1 [2-OMe, 4-OMe, 5-Cl] " means It represents "2,4-dimethoxy-5-chlorophenyl", and the description "Z-2 [4-Me]" represents "5-methylfuran-2-yl". Further, in the case of no substitution, it is represented by "-", and for example, the description of "Z-1 [-]" represents "phenyl".

In addition, the description of "* 1" in the table means "resin-like".

[Table 1]

-------------------------------------------------- -
No. Z ⁴ Z mp (℃)
-------------------------------------------------- -
1-001 OMe Z-1 [2-OMe, 4-OMe] * 1
1-002 Me Z-1 [2-OMe, 4-OMe] 248-250
1-003 Me Z-1 [2-OMe, 4-OMe, 5-OMe] 230-232
1-004 OMe Z-1 [2-OMe, 4-OMe, 6-OMe] * 1
1-005 OMe Z-1 [2-OMe, 3-OMe, 4-OMe] * 1
1-006 OMe Z-1 [2-OMe, 4-OMe, 6-Me] 242-244
1-007 Me Z-1 [2-OMe, 4-OMe, 6-Me] 229-231
1-008 Me Z-1 [2-OMe, 4-OMe, 6-Br] 234-236
1-009 OMe Z-1 [2-OMe, 4-OMe, 5-Br] 202-204
1-010 Me Z-1 [2-OMe, 4-OMe, 5-Br] 129-131
1-011 OMe Z-1 [2-OMe, 4-OMe, 5-Cl] 200-202
1-012 Me Z-1 [2-OMe, 4-OMe, 5-Cl] 128-130
1-013 OMe Z-1 [2-OEt, 4-OEt] 170-172
1-014 Me Z-1 [2-OEt, 4-OEt] 129-131
1-015 OMe Z-1 [2-On-Pr, 4-On-Pr] 105-107
1-016 Me Z-1 [2-On-Pr, 4-On-Pr] 104-106
1-017 OMe Z-1 [2-OMe, 4-OMe, 5-CH ₂ CN] * 1
1-018 Me Z-1 [2-OMe, 4-OMe, 5-CH ₂ CN] 232-234
1-019 Me Z-1 [2-OMe, 3-Me, 4-OMe] 116-118
1-020 Me Z-1 [2-OMe, 4-OMe, 6-OMe] 246-248
1-021 OMe Z-1 [2-OMe] * 1
1-022 OMe Z-1 [3-OMe] * 1
1-023 OMe Z-1 [4-OMe] * 1
1-024 OMe Z-1 [3-OMe, 4-OMe] 170-173
1-025 OMe Z-1 [3-OMe, 5-OMe] 114-116
1-026 OEt Z-1 [2-OMe, 4-OMe] * 1
1-027 OMe Z-1 [4-OCF ₃ ] * 1
1-028 OMe Z-1 [3-OCF ₃ ] * 1
1-029 OMe Z-1 [4-On-Pr] * 1
1-030 OMe Z-1 [3-SMe] 110-111
1-031 OMe Z-1 [4-i-Pr] 199-201
1-032 OMe Z-1 [4-C (O) OMe] * 1
1-033 OMe Z-1 [4-NMe ₂ ] * 1
1-034 OMe Z-1 [4-C (= NOMe) Me * 1
1-035 OMe Z-1 [-] * 1
1-036 OMe Z-1 [2-F, 4-F] * 1
1-037 OMe Z-1 [2-Me] * 1
1-038 OMe Z-1 [4-Me] 95-97
1-039 OMe Z-1 [4-SMe] * 1
1-040 OMe Z-2 [-] * 1
1-041 OMe Z-2 [4-CH ₂ OCH ₃ ] 70-73
1-042 OMe Z-2 [4-Me] 152-155
1-043 OMe Z-2 [4-Et] * 1
1-044 OMe Z-2 [4-n-Pr] 64-67
-------------------------------------------------- -
^{Table 2 shows 1 1} H-NMR data of the compounds of the present invention for which the melting point is not described.

The symbols in Table 2 have the following meanings. brs: Broad singlet, m: Multiplet. The description of "* 3" indicates that the signal corresponding to the hydroxy proton was not observed.

[Table 2]
――――――――――――――――――――――――――――――――――――――
No. ¹ H-NMR (CDCl ₃ , Me ₄ Si, 300MHz)
――――――――――――――――――――――――――――――――――――――
1-001; δ7.2-7.05 (m, 1H), 6.8-6.6 (m, 3H), 6.75-6.6 (m, 2H), 4.55-3.85 (m, 1H), 3.85-3.7 (m, 9H) , 3.25-2.4 (m, 2H), 2.33 (brs, 3H), 2.25-2.15 (m, 3H).
1-004; δ6.8-6.4 (m, 3H), 6.2-6.05 (m, 2H), 4.85-4.25 (m, 1H), 3.9-3.6 (m, 12H), 3.2-2.6 (m, 2H) , 2.33 (s, 3H), 2.3-2.15 (m, 3H).
1-005 (* 3); δ7.0-6.55 (m, 4H), 4.55-3.7 (m, 13H), 3.2-2.45 (m, 2H), 2.4-2.25 (m, 3H), 2.2-2.1 ( m, 3H).
1-017 (* 3); δ6.8-6.4 (m, 4H), 4.55-3.5 (m, 10H), 3.2-2.5 (m, 2H), 2.4-2.15 (m, 8H).
1-021 (* 3); δ7.4-6.55 (m, 6H), 4.7-3.7 (m, 7H), 3.2-2.4 (m, 2H), 2.35-2.1 (m, 6H).
1-022 (* 3); δ7.35-6.6 (m, 6H), 4.55-3.7 (m, 7H), 3.35-2.45 (m, 2H), 2.35-2.05 (m, 6H).
1-023 (* 3); δ7.3-7.3 (m, 2H), 6.9-6.5 (m, 4H), 4.4-3.65 (m, 7H), 3.15-2.4 (m, 2H), 2.31 (s, 3H), 2.13 (s, 3H).
1-026 (* 3); δ7.3-6.4 (m, 5H), 4.6-3.7 (m, 9H), 3.25-2.35 (m, 2H), 2.35-2.0 (m, 6H), 1.45-1.3 ( m, 3H).
1-027 (* 3); δ7.4-7.15 (m, 4H), 6.8-6.5 (m, 2H), 4.25-3.7 (m, 4H), 3.3-2.4 (m, 2H), 2.4-2.0 ( m, 6H).
1-028 (* 3); δ7.4-7.1 (m, 4H), 6.8-6.5 (m, 2H), 4.25-3.7 (m, 4H), 3.35-2.4 (m, 2H), 2.4-2.0 ( m, 6H).
1-029 (* 3); δ7.4-7.1 (m, 2H), 7.0-6.45 (m, 4H), 4.2-3.45 (m, 6H), 3.3-2.4 (m, 2H), 2.4-2.0 ( m, 6H), 1.9-1.7 (m, 2H), 1.1-1.0 (m, 3H).
1-032 (* 3); δ8.05-7.95 (m, 2H), 7.45-7.3 (m, 2H), 6.8-6.55 (m, 2H), 4.25-3.75 (m, 7H), 3.3-2.4 ( m, 2H), 2.4-2.0 (m, 6H).
1-033 (* 3); δ7.3-7.1 (m, 2H), 6.75-6.55 (m, 4H), 4.1-3.7 (m, 4H), 3.2-2.4 (m, 8H), 2.4-2.0 ( m, 6H).
1-034 (* 3); δ7.65-7.55 (m, 2H), 7.35-7.2 (m, 2H), 7.8-7.55 (m, 2H), 4.2-3.75 (m, 7H), 3.3-2.4 ( m, 2H), 2.4-2.0 (m, 9H).
1-035 (* 3); δ7.4-6.3 (m, 7H), 4.3-3.5 (m, 4H), 3.35-2.4 (m, 2H), 2.4-2.0 (m, 6H).
1-036 (* 3); δ7.4-6.4 (m, 5H), 4.2-3.5 (m, 4H), 3.3-2.4 (m, 2H), 2.4-2.0 (m, 6H).
1-037 (* 3); δ7.4-6.55 (m, 6H), 4.5-3.7 (m, 4H), 3.35-2.0 (m, 11H).
1-039 (* 3); δ7.7-7.45 (m, 2H), 7.3-7.15 (m, 2H), 6.8-6.6 (m, 2H), 4.2-3.6 (m, 4H), 3.3-2.0 ( m, 11H).
1-040 (* 3); δ6.9-6.2 (m, 5H), 4.2-3.7 (m, 4H), 3.2-2.6 (m, 2H), 2.35-2.0 (m, 6H).
1-043 (* 3); δ6.9-5.85 (m, 4H), 4.3-3.7 (m, 4H), 3.2-2.5 (m, 2H), 2.4-2.0 (m, 8H), 1.3-1.15 ( m, 3H).
――――――――――――――――――――――――――――――――――――――
Test Examples Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples, but the present invention is not limited to these.
[Test Example 1] Test of herbicidal effect by pretreatment for weed growth under flooded conditions After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to obtain a flooded condition with a water depth of 4 cm. After the seeds of Tainubie were mixedly sown in the above cup, rice seedlings at the 2.5 leaf stage were transplanted. On the day of sowing, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dosage and treated on the surface of the water. The cups were placed in a greenhouse at 25 to 30 ° C. to grow plants, and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the following criteria. The results are shown in Table 3.

Judgment Criteria 5 ... Weed killing rate 90% or more (almost complete death)
4… Weeding rate 70% or more and less than 90% 3… Weeding rate 40% or more and less than 70% 2… Weeding rate 20% or more and less than 40% 1… Weeding rate 5% or more and less than 20% 0… Weeding rate 5% or less (almost effective) none)
[Test Example 2] Test of herbicidal effect by weed growing season treatment under flooded conditions After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to obtain a flooded condition with a water depth of 4 cm. The seeds of Tainubier were mixedly sown in the above cups and placed in a greenhouse at 25 to 30 ° C. to grow plants. When Tainubie reached the 1st or 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dosage and treated on the surface of the water. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 4.
[Test Example 3] Test of herbicidal effect by foliage treatment After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to make the condition of water depth 0.1 to 0.5 cm. Seeds of barnyard grass, leptochloa zebra and rice were sown and placed in a greenhouse at 25 to 30 ° C. to grow plants. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage, and the foliage was uniformly treated with a small spray. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 5.
[Test Example 4] Test of herbicidal effect by soil treatment Put sterilized corn soil in a plastic box with a length of 21 cm, a width of 13 cm, and a depth of 7 cm. Seeds of corn, soybean, wheat, beet and rapeseed were sown in spots and covered with soil by about 1.5 cm. Next, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage, and the soil surface was uniformly treated with a small spray. Plants were grown by placing a plastic box in a greenhouse at 25 to 30 ° C., and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 6.
[Test Example 5] Test of herbicidal effect by foliage treatment Put sterilized corn soil in a plastic box with a length of 21 cm, a width of 13 cm, and a depth of 7 cm. Seeds of corn, soybean, wheat, beet and rapeseed were sown in spots, covered with soil of about 1.5 cm, and then the plants were grown in a greenhouse at 25 to 30 ° C. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage, and the foliage was uniformly treated with a small spray. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 7.

The symbols in Tables 3 to 7 have the following meanings.
A: Tainubier, B: Azegaya, C: Mehishiba, D: Enocologsa, E: Inubier, F: Karasumugi, G: Blackgrass, H: Italian ryegrass, I: Seiyounukabo, a: Transplanted rice, b: Directly sown rice, c : Corn, d: Soybean, e: Wheat, f: Beet, g: Rapeseed In addition, the treated dose (g / ha) is the gram (g) of the value described when converted per hectare (1 ha). Indicates that the concentration has been adjusted so that only the number is processed.

[Table 3]
―――――――――――――――――――――――――
No. Processing dose A a
(g / ha)
―――――――――――――――――――――――――
1-001 80 5 1
1-002 320 5 0
1-004 320 3 0
1-013 80 5 0
1-019 80 3 0
1-021 320 4 3
1-022 320 3 3
1-023 320 5 4
1-026 80 3 0
1-027 80 4 0
1-028 80 3 0
1-029 80 5 0
1-030 80 3 0
1-032 80 4 0
1-034 80 5 3
1-037 80 5 0
1-038 80 3 0
1-040 320 5 5
―――――――――――――――――――――――――
[Table 4]
―――――――――――――――――――――――――
No. Processing dose A
(g / ha)
―――――――――――――――――――――――――
1-001 80 3
1-005 80 3
1-009 80 3
1-011 80 4
1-013 80 3
1-014 80 3
1-015 80 3
1-019 80 4
1-021 320 5
1-022 320 4
1-023 320 5
1-024 80 3
1-029 80 3
1-034 80 3
1-037 80 3
1-040 320 5
―――――――――――――――――――――――――
[Table 5]
―――――――――――――――――――――――――
No. Treatment dose EB b
(g / ha)
―――――――――――――――――――――――――
1-001 80 5 5 4
1-002 320 4 4 0
1-004 320 3 0 0
1-005 80 4 3 3
1-006 80 3 0 0
1-008 80 3 0 0
1-009 80 3 0 0
1-011 80 3 3 0
1-013 80 4 3 3
1-014 80 4 3 3
1-015 80 3 3 0
1-016 80 0 3 3
1-017 157 3 3 0
1-019 80 3 3 3
1-020 80 3 0 1
1-021 320 5 5 5
1-022 320 4 5 5
1-023 320 5 5 5
1-024 80 5 5 5
1-025 80 3 3 5
1-026 80 4 4 0
1-027 80 4 5 5
1-029 80 4 5 5
1-030 80 4 3 3
1-031 80 3 5 4
1-032 80 4 5 5
1-033 80 4 5 0
1-034 80 4 5 3
1-035 80 4 5 0
1-036 80 4 5 2
1-037 80 5 4 3
1-038 80 4 5 4
1-040 320 5 5 5
1-041 320 5 4 2
1-042 80 4 5 3
1-043 80 3 5 0
1-044 80 3 4 0
―――――――――――――――――――――――――
[Table 6]
――――――――――――――――――――――――――――
No. Treatment dose CDEFGHI cdefg
(g / ha)
――――――――――――――――――――――――――――
1-001 80 2 5 5 1 0 4 4 0 0 0 0 0
1-002 320 3 4 2 0 0 0 0 0 0 0 0 0
1-011 80 0 0 0 0 5 5 5 0 0 0 0 0
1-013 80 3 4 0 0 3 5 5 1 0 0 0 0
1-021 320 4 4 5 1 0 4 4 3 0 0 0 0
1-022 320 3 1 4 0 0 4 1 0 0 0 0
1-023 320 5 5 5 3 4 5 5 3 0 0 0 0
1-027 80 0 0 0 0 1 5 0 0 0 0 0
1-034 80 3 4 3 0 3 4 4 1 0 0 0 0
1-037 80 0 0 0 0 0 4 3 0 0 0 0 0
1-038 80 0 0 0 0 0 3 2 0 0 0 0 0
1-040 320 4 4 5 5 5 5 5 4 0 3 0 0
――――――――――――――――――――――――――――
[Table 7]
――――――――――――――――――――――――――――
No. Treatment dose CDEFGHI cdefg
(g / ha)
――――――――――――――――――――――――――――
1-001 80 4 5 5 5 5 5 5 5 0 4 0 0
1-002 320 4 4 3 0 4 5 0 3 0 0 0 0
1-005 80 3 3 3 3 5 5 5 1 0 2 0 0
1-009 80 1 3 3 1 5 4 5 1 0 0 0 0
1-011 80 2 0 2 0 5 5 5 0 0 0 0 0
1-013 80 3 2 3 5 5 5 5 0 0 3 0 0
1-014 80 1 0 1 0 5 5 0 0 0 0 0 1
1-015 80 0 1 3 1 4 2 5 0 0 0 0 0
1-019 80 0 2 3 0 0 3 0 1 0 1 0 3
1-021 320 5 5 5 4 5 5 5 4 0 0 0 1
1-022 320 1 4 5 2 5 5 5 1 0 0 0 4
1-023 320 5 5 5 4 5 5 5 5 1 2 0 4
1-024 80 4 5 5 3 5 4 4 5 1 2 0 3
1-026 80 0 3 4 0 4 3 1 0 0 0 0
1-027 80 2 4 4 0 5 5 5 1 0 1 0 4
1-028 80 0 0 0 0 0 3 0 0 0 0 0 1
1-029 80 5 4 5 1 5 5 5 5 0 3 0 3
1-030 80 2 3 2 0 0 0 0 2 0 0 0 0
1-031 80 0 0 0 0 5 5 3 2 0 0 0 1
1-032 80 0 0 0 0 0 2 3 1 0 1 0 4
1-033 80 4 4 4 0 0 1 0 2 0 1 0 0
1-034 80 5 5 4 1 5 5 5 5 2 4 0 2
1-035 80 0 0 3 0 2 3 0 1 0 0 0 0
1-036 80 0 0 4 0 0 2 0 0 0 0 0 0
1-037 80 3 3 5 3 4 5 4 3 0 0 0 0
1-038 80 0 0 2 2 4 5 3 3 0 0 0 2
1-040 320 5 5 5 5 5 5 5 5 3 5 0 4
1-041 320 2 3 5 0 0 0 0 3 0 0 0 0
1-042 80 1 2 3 0 0 1 0 1 0 0 0 0
――――――――――――――――――――――――――――

The cyclopentene compound of the present invention is a novel compound and is useful as a selective herbicide for rice, corn, soybean, wheat, beet and rapeseed.

Claims (3)

Equation (1):

[In the formula, A represents a hydrogen atom,
Z ⁴ represents methyl or methoxy,
Z ⁶ and Z ⁸ represent methyl,
Z represents Z-1 or Z-2

t3 represents an integer of 0 or 1 and represents
t5 represents an integer of 0, 1, 2 or 3
X ¹ is a halogen atom, C _{1 to} C ₆ alkyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C _{1 to} C ₆ alkyl thio, C _{1 to} C ₆ alkoxycarbonyl, C (= NOR). ¹ ) Represents (C _{1- C 6} ) alkyl ^{substituted with R 2} , N (R ³ ) R ⁴ or R ^5.
R ¹ , R ² , R ³ and R ⁴ independently represent _{C 1 to} C ₆ alkyl, respectively.
R ⁵ represents C _{1 to} C ₆ alkoxy or cyano. ], A cyclopentene compound or a salt thereof. A pesticide containing at least one selected from the cyclopentene compound according to claim 1 and a salt thereof as an active ingredient. A herbicide containing at least one selected from the cyclopentene compound according to claim 1 and a salt thereof as an active ingredient.