EP0258391A1 - Use of heterocyclic nitrogen-containing compounds for reducing moisture loss from plants and increasing crop yield - Google Patents
Use of heterocyclic nitrogen-containing compounds for reducing moisture loss from plants and increasing crop yieldInfo
- Publication number
- EP0258391A1 EP0258391A1 EP87901826A EP87901826A EP0258391A1 EP 0258391 A1 EP0258391 A1 EP 0258391A1 EP 87901826 A EP87901826 A EP 87901826A EP 87901826 A EP87901826 A EP 87901826A EP 0258391 A1 EP0258391 A1 EP 0258391A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- substituted
- unsubstituted
- halogen
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 230000001965 increasing effect Effects 0.000 title claims abstract description 12
- -1 nitrogen-containing heterocyclic compound Chemical class 0.000 claims abstract description 819
- 238000000034 method Methods 0.000 claims abstract description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 260
- 229910052736 halogen Inorganic materials 0.000 claims description 188
- 150000002367 halogens Chemical class 0.000 claims description 176
- 150000003839 salts Chemical class 0.000 claims description 154
- 125000003342 alkenyl group Chemical group 0.000 claims description 148
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 136
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 126
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 126
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 126
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 124
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 115
- 125000003545 alkoxy group Chemical group 0.000 claims description 114
- 125000001424 substituent group Chemical group 0.000 claims description 112
- 229910052739 hydrogen Inorganic materials 0.000 claims description 104
- 239000001257 hydrogen Substances 0.000 claims description 104
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 101
- 125000004414 alkyl thio group Chemical group 0.000 claims description 95
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 94
- 150000002431 hydrogen Chemical class 0.000 claims description 93
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 125000000304 alkynyl group Chemical group 0.000 claims description 83
- 229910052760 oxygen Inorganic materials 0.000 claims description 76
- 229910052717 sulfur Inorganic materials 0.000 claims description 76
- 125000004423 acyloxy group Chemical group 0.000 claims description 75
- 125000001188 haloalkyl group Chemical group 0.000 claims description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 241000196324 Embryophyta Species 0.000 claims description 73
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 73
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 72
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 71
- 125000003435 aroyl group Chemical group 0.000 claims description 71
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 71
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 71
- 125000004104 aryloxy group Chemical group 0.000 claims description 70
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 68
- 125000005110 aryl thio group Chemical group 0.000 claims description 68
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 65
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 65
- 125000005333 aroyloxy group Chemical group 0.000 claims description 65
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 65
- 125000001769 aryl amino group Chemical group 0.000 claims description 65
- 150000004676 glycans Chemical class 0.000 claims description 64
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 63
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 63
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 63
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims description 63
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 63
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 63
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 63
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 63
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 63
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 63
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 63
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 63
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 63
- 125000005239 aroylamino group Chemical group 0.000 claims description 63
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 63
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 63
- 125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 63
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 63
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 63
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 63
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 63
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 63
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 63
- 125000005252 haloacyl group Chemical group 0.000 claims description 63
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 63
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 63
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 63
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 63
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 63
- 229920001282 polysaccharide Polymers 0.000 claims description 63
- 239000005017 polysaccharide Substances 0.000 claims description 63
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 63
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 63
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 63
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 63
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 62
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 62
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 62
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 62
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 62
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 61
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 61
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 61
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 60
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 60
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 59
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 59
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims description 59
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 54
- 125000005842 heteroatom Chemical group 0.000 claims description 51
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 48
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 48
- 229920006395 saturated elastomer Polymers 0.000 claims description 44
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 125000002252 acyl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000004122 cyclic group Chemical group 0.000 claims description 25
- 125000002837 carbocyclic group Chemical group 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 20
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000001118 alkylidene group Chemical group 0.000 claims description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 230000000243 photosynthetic effect Effects 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
- 101150065749 Churc1 gene Proteins 0.000 claims description 6
- 102100038239 Protein Churchill Human genes 0.000 claims description 6
- 208000005156 Dehydration Diseases 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 125000004442 acylamino group Chemical group 0.000 claims 9
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- 125000006357 methylene carbonyl group Chemical group [H]C([H])([*:1])C([*:2])=O 0.000 claims 8
- 125000000732 arylene group Chemical group 0.000 claims 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 6
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 6
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims 6
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 6
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 6
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims 4
- 244000061176 Nicotiana tabacum Species 0.000 claims 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 4
- 240000003768 Solanum lycopersicum Species 0.000 claims 4
- 230000003698 anagen phase Effects 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- 230000001850 reproductive effect Effects 0.000 claims 4
- 239000002689 soil Substances 0.000 claims 4
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 3
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 3
- QVFHFKPGBODJJB-UHFFFAOYSA-N 1,3-oxathiane Chemical compound C1COCSC1 QVFHFKPGBODJJB-UHFFFAOYSA-N 0.000 claims 3
- WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 claims 3
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 3
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims 3
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims 3
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 claims 3
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 claims 3
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims 3
- YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 claims 3
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims 3
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 3
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 3
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 3
- 150000001602 bicycloalkyls Chemical group 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims 3
- 125000001485 cycloalkadienyl group Chemical group 0.000 claims 3
- 125000002772 cycloalkatrienyl group Chemical group 0.000 claims 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 3
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 3
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims 3
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims 3
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 3
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 3
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims 3
- SCXKWEIRWVHPIN-UHFFFAOYSA-N pyran-2-thione Chemical compound S=C1C=CC=CO1 SCXKWEIRWVHPIN-UHFFFAOYSA-N 0.000 claims 3
- WWANKXYUVUCOMI-UHFFFAOYSA-N pyran-4-thione Chemical compound S=C1C=COC=C1 WWANKXYUVUCOMI-UHFFFAOYSA-N 0.000 claims 3
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 3
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 229930192474 thiophene Natural products 0.000 claims 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
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- C07—ORGANIC CHEMISTRY
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
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- C—CHEMISTRY; METALLURGY
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- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/04—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
Definitions
- This invention relates to the use of heterocyclic nitrogen-containing compounds for reducing transpirational moisture loss from plants and also for increasing crop yield. This invention further relates to novel heterocyclic nitrogen-containing compounds and processes for the preparation thereof.
- Transpiration is a well known physiolpgical process involving the passage of water in the form of a vapor through living tissues.
- the water vapor passes through plant stomatal openings into the atmosphere, thus facilitating the absorption and translocation of aqueous nutrients by plant root systems.
- the stomatal openings also permit necessary gaseous interchange between plant tissues and the external air. It is believed that only about one percent of the total water absorbed by plant roots is used for plant growth, the remainder being released through plant stomatal openings into the atmosphere by transpiration.
- transpiration water loss from plants is important for several reasons; in particular, for decreasing requirements for irrigation water especially in dry climate regions, for protecting plants from wilting or other damage during transplantation or shipment or during severe cold weather, and for alleviating water stress in certain types of environments.
- Water stress as used herein occurs when the transpiration rate exceeds the rate of water uptake by the plant. Water stress appears as a decrease in plant water potential and turgor and can result in wilting or other forms of damage or even plant death.
- This invention relates to a method for reducing moisture loss from plants which comprises applying to the plant surface an effective amount, sufficient to reduce moisture loss from the plant surface without substantially inhibiting plant photosynthetic electron transport, of a compound having the formula:
- R 1 , R 2 and X are as defined hereinafter.
- This invention also relates to a method of increasing crop yield which comprises applying to the crop an effective amount, sufficient to increase crop yield without substantially inhibiting plant photosynthetic electron transport, of a compound having the formula:
- R 1 , R 2 and X are as defined hereinafter.
- This invention further relates to novel heterocyclic nitrogen-containing compounds and also to processes for the preparation of said compounds.
- this invention relates to a method of reducing moisture loss from plants and increasing crop yields by the use of certain heterocyclic nitrogen-containing compounds. More particularly, this invention involves a method for reducing transpirational moisture loss from plants and increasing crop yield which comprises applying to the plant surface or crop an effective amount, sufficient to reduce moisture loss from the plant surface or to increase crop yield without substantially inhibiting plant photosynthetic electron transport, of a compound having the formula:
- R 1 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylaIkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl,
- R 1 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, aIkylcarbonylaIkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkyIsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, diaIky
- X is a covalent single bond or double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbony
- R 2 is a substituted or unsubstituted, heterocyclic ring system having at least one nitrogen atom which is selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulf
- R 3 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamid
- -X - R 3 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylamino
- Y 1 and Y 4 are independently oxygen or sulfur
- Y 2 and Y 3 are independently oxygen. sulfur, amino or a covalent bond;
- R 4 and R 5 are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl in which the permissible substituents (Z) are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, a1
- alkenyl, haloalkenyl or polyhaloalkenyl alkylthio, polyhaloalkylthio, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkylsulfonylamino, aIkylcarbonylamino, polyhaloalkylsulfonylamino, polyhaloalkylcarbonylamino, trialkylsilyl, aryldialkylsilyl, triarylsilyl, sulfonic acid and derivative salts, phosphonic acid and derivative salts, alkoxycarbonylamino, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkenyl, polyhaloalkenyl, alkenyloxy, alkynyl, alkynyloxy, polyhaloalkenyloxy, polyhaloalkynyl,
- the alkyl-containing moieties above may contain from about 1 to about 100 carbon atoms or greater, preferably from about 1 to about 30 carbon atoms, and more preferably from about 1 to about 20 carbon atoms.
- the polysaccharide moiety may contain up to about 50 carbon atoms. It is appreciated that all compounds encompassed within formula 1 are compounds having no unfilled bonding positions. It is further appreciated that in order for a substi-tuent to be permissible for the compounds encompassed within formula 1, the valence of the substituent must be appropriate with the bonding capability of the particular carbon atom or heteroatom.
- B 1 represents a saturated or unsaturated carbon atom and A 1 represents a ring-forming chain of atoms which together with B 1 forms a cyclic system containing from 0 to 4 double bonds or from 0 to 2 triple bonds.
- a 1 may contain entirely from 2 to 12 carbon atoms, may contain a combination of from 1 to 11 carbon atoms and from 1 to 4 heteroatoms which may be selected independently from N, O, S, P or other heteroatoms, or may contain 4 ring-forming heteroatoms alone.
- Monocyclic ring systems encompassed by R 2 in formula 1 may include any monocyclic ring system of R 1 and R 3 having at least one nitrogen atom.
- Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic and aliphatic N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide moieties.
- Selected carbon atoms contained in cycles formed by B 1 and A 1 containing more than 3 ring-forming atoms may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino groups or substituted or unsubstituted methylidene groups.
- the group designated as Z represents one or more substituents selected independently from among the group of substituents defined for Z herein.
- the cycle formed by B 1 and A 1 contains fewer than 4 ring forming members, it should be a saturated carbocycle, i.e. cyclopropyl.
- the cycle formed by B and A contains fewer than 5 ring-forming members, it should contain no more than 1 heteroatom.
- Bicyclic ring systems encompassed by R 1 and R 3 in formula 1 may be represented by generalized formulae 3 and 4 as follows:
- B 2 and B 3 may be independently a saturated or unsaturated carbon atom or a saturated nitrogen atom
- a 2 and A 3 independently represent the ring-forming chains of atoms described below and Z represents one or more substituents selected independently from among the group of substituents defined for Z herein.
- Combinations of A 2 and A 3 may contain in combination with B 2 or B 3 from 0 to 5 double bonds.
- a 2 and A 3 independent of B 2 and B 3 , may contain entirely from 1 to 11 carbon atoms, may contain a combination of 1 to 3 heteroatoms which may be selected independently from among N, O, S, P of other heteroatoms together with from 1 to 10 carbon atoms or may contain from 1-3 ring-forming heteroatoms alone.
- Ring-forming heteroatoms may in some cases bear oxygen atoms, as in aromatic and aliphatic
- N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups are N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups.
- Selected carbon atoms contained in A 2 and A 3 may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino groups or substituted or unsubstituted methylidene groups.
- Bicyclic ring systems encompassed by R 2 in formula 1 may include any bicyclic ring system of R 1 and R 3 having at least one nitrogen atom.
- bicyclic ring systems defined for R 1 and R 3 may be spirocyclic ring systems and are not limited to the fused bicyclic structures of formulae 3 and 4.
- Spirocyclic ring systems may be saturated or unsaturated carbocyclic or- heterocyclic and may be independently substituted by one or more substituents Z as defined herein.
- Polycyclic ring systems i.e., greater than 2 rings, encompassed by R 1 and R 3 in formula 1 may be represented by generalized formulae 5, 6, 7 and 8 as follows:
- B 4 , B 5 , B 6 and B 7 may be independently a saturated or unsaturated carbon atom or a saturated nitrogen atom, and A 4 , A 5 , A 6 and A 7 independently represent ring forming chains of atoms which may contain together with one or the other (but not both) of their two associated bridgehead atoms, from 0-2 double bonds.
- Z represent one or more substituents selected independently from among the group of substituents defined for Z herein.
- the ring-forming elements of A 4 , A 5 , A 6 and A 7 independent of B 4 , B 5 , B 6 and B 7 may contain from 1-11 carbon atoms, may contain a combination of from 1-10 carbon atoms and from 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 1-3 heteroatoms alone.
- Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic N-oxides and ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups.
- the group A 6 may at times be defined as a bond.
- Selected carbon atoms contained in A 4 , A 5 , A 6 and A 7 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups.
- the groups B 8 , B 9 and B 10 represent independently a saturated or unsaturated carbon atom or a saturated nitrogen atom.
- the group B 11 may represent a saturated or unsaturated carbon atom or a nitrogen or phosphorous atom.
- the groups A 8 , A 9 and A 10 represent ring-forming chains of atoms which may contain together with 1 of the groups B 8 , B 9 , B 10 and B 11 from 0-2 double bonds.
- the ring-forming elements of groups A 8 , A 9 and A 10 independent of groups B 8 , B 9 , B 10 and B 11 may contain from 2-10 carbon atoms, may contain from 1-10 carbon atoms in combination with 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 2-3 heteroatoms alone. Ring-forming heteroatoms may in some cases bear oxygen atoms as in aromatic N-oxides and in ring systems containing the sulfinyl, sulfonyl, selenoxide and phosphine oxide groups. Selected carbon atoms contained in groups A 8 , A 9 and A 10 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups.
- polycyclic ring systems defined for R 1 and R 3 may be spirocyclic ring systems and are not limited to the fused polycyclic structures of formulae 5, 6, 7 and 8.
- Spirocyclic ring systems may be saturated or unsaturated, carbocyclic or heterocyclic and may be independently substituted by one or more substituents Z as defined herein.
- Polycyclic ring systems encompassed by R 2 of formula 1 may include any polycyclic ring system or R 1 and R 3 having at least one nitrogen atom.
- Illustrative polycyclic ring structures which are encompassed by R 1 and R 3 in formula 1 include the following:
- Bridged bicyclic structures encompassed by R 1 and R 3 in formula 1 may be represented by generalized formulae 9, 10, and 11 as follows:
- B 12 and B 13 may be independently a saturated carbon atom optionally substituted by Z or a nitrogen atom, and the groups A 11 , A 12 and A 13 independently represent ring-forming chains of atoms which may contain, independently of B 12 and B 13 , from 0-2 double bonds.
- the groups Z represent one or more substituents selected independently from among the groups of substituents defined for Z herein.
- the ring-forming elements of A 11 , A 12 and A 13 may contain entirely from 1-11 carbon atoms, may contain a combination of from 1-10 carbon atoms and from 1-3 heteroatoms which may be selected independently from among N, O, S, P or other heteroatoms, or may contain from 1-3 heteroatoms alone with the proviso that when one of the groups A 11 , A 12 and A 13 is a single heteroatom, the other two groups should contain two or more ring-forming atoms.
- a second proviso is that when one or both of the groups B 12 and B 13 is nitrogen, the groups A 11 , A 12 and A 13 should contain at least two saturated ring-forming atoms.
- Ring-forming heteroatoms may in some cases bear oxygen atoms as in the sulfinyl, sulfonyl, selenoxide and phosphine oxide moieties.
- Selected carbon atoms contained in A 11 , A 12 and A 13 may bear one or more carbonyl, thiocarbonyl or substituted or unsubstituted imino groups.
- Bridged bicyclic structures encompassed by R 2 of formula 1 may include any bicyclic bridged system of R 1 and R 3 having at least one nitrogen atom.
- the substituent X may be an unsubstituted heteroatom such as an oxygen or sulfur, as in carbonyl and thiocarbonyl systems, or may be a substituted heteroatom or carbon atom.
- X may also be a covalent single or double bond.
- X may further be a saturated or unsaturated, branched or straight chain of carbon atoms; a branched or straight, saturated or unsaturated chain of atoms consisting of both carbon atoms and heteroatoms; or may be a branched or straight, saturated or unsaturated chain consisting entirely of heteroatoms.
- Selected heteroatomic components of X may bear oxygen atoms as in the case of groups containing the sulfonyl, sulfinyl, N-oxide and phosphine oxide moieties.
- Selected heteroatomic components of X may bear one or more substituents Z as defined herein.
- Selected carbon atoms participating in X may bear carbonyl, thiocarbonyl, substituted or unsubstituted imino, substituted or unsubstituted alkylidene or one or more substituents Z as defined herein.
- R 10 and R 11 are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl in which the permissible substituents are as defined for Z herein.
- formula 1 encompasses a wide variety of heterocyclic nitrogen-containing compounds.
- Illustrative heterocyclic nitrogen-containing compounds within the scope of formula 1 which may be used for reducing transpirational moisture loss from plants and increasing crop yield are included in Tables 1 through 43 below.
- novel heterocyclic nitrogen-containing compounds of this invention can be depicted by the following formulae:
- R 24 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl; x 10 represents O, S, SO, SO 2 , NH,
- Y 19 is the same or different and represents halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl; provided that (i) at least two ring position pairs selected from 2 and 4, 2 and 6, 2 and 3, and 3 and 4 are substituted with the same or different halogen; (ii) when ring positions 2,4 and 6 are substituted with chlorine and j is a value of 0 and X 10 is
- R 24 is not unsubstituted phenyl
- R 25 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X 11 represents O, S, SO, SO 2 , NH,
- b is a value of 2 to 3;
- Y 20 is the same or different and represents halogen, alkyl, cyano, polyhaloalkyl, polyhaloalkoxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl provided that at least two ring position pairs selected from 2 of Y 20 are halogen;
- R 26 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X 12 represents O, S, SO, SO , NH,
- Y 21 and Y 22 are independently the same or different halogen
- Y 23 represents hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl;
- R 27 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X represents O, S, SO, SO 2 , NH,
- Y 24 represents halogen
- Y 25 and Y 26 independently represent hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl provided that at least one of Y 25 and Y 26 is halogen and further provided that when Y 24 , Y 25 and Y 26 are chloro and X 13 is O, then R 27 is not unsubstituted phenyl;
- R 28 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X 14 represents O, S, SO, SO 2 , NH,
- Y 27 and Y 28 are independently halogen
- Y 29 represents hydrogen, halogen, alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl;
- R 29 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X 15 represents O, S, SO, SO 2 , NH,
- Y 30, Y 31 and Y 32 independently represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro. acyl or polyhaloalkylsulfonyl provided that at least 2 of
- Y 30 , Y 31 and Y 32 are halogen
- R 30 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X 16 represents O, S, SO, SO 2 , NH,
- Y 33 , Y 34 and Y 35 independently represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl or polyhaloalkylsulfonyl provided that (i) at least 2 of Y 33 , Y 34 and Y 35 are halogen, (ii) when Y 34 and Y 35 are both chloro and X 16 is O, then
- R 30 is not unsubstituted phenyl, and (iii) when Y 33 and Y 34 are both chloro and X 16 is O, the
- R 30 is not unsubstituted phenyl or 4-methoxyphenyl
- d is a value of from 0 to 4 inclusive
- e is a value of 1 or 2 provided that d and e are not greater than 5;
- R 31 is the same or different and represents unsubstituted or substituted aryl provided that when R 31 is 2- or 4-aryl then d is not O, aralkyl provided that when R 31 is R-aralkyl then d is not O, alkoxy.
- cycloalkoxy, aryloxy, aralkoxy provided that when R 31 is 4-aralkoxy then d is not O, arylaryloxy, aralkoxyaralkyl, arylaralkoxy.aryloxyaralkyl, aryloxyalkyl, aryloxyaryloxy, aralkoxyaralkoxy, aryloxyalkoxy, alkylthio, alkenylthio, arylthio, aralkylthio, arylthioaralkyl, arylsulfonylarylsulfonyl, alkylamino, dialkylamino, acyloxy, aroyloxy, alkoxycarbonyloxy, phenylazo provided that X 17 is O or S, naphthylazo, or -OCH 2 O- or -OCH 2 CH 2 O which join adjacent carbon atoms to form a five- or six-membered ring;
- X 17 represents O, S, NH, CH 2 , -CH 2 O-, -CH 2 S- or -OCH 2 CH 2 O-;
- Y 37 represents halogen
- Y 38 represents halogen, alkoxy. alkylthio, alkylsulfonyl, polyhaloalkoxy, polyhaloalkyl, cyano, nitro or unsubstituted or substituted arylthio, aryloxy or arylsulfonyl;
- f is a value of from 0 to 5;
- R 32 is the same or different and represents halogen, alkyl, alkenyl, alkynyl, polyhaloalkyl, cyano, nitro, alkylamino, dialkylamino, alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, CO 2 (alkyl), CONH(alkyl), CON(alkyl) 2 , SO 2 N(alkyl) 2 , alkylcarbonyloxy, alfcoxycarbonyloxy, or unsubstituted or substituted aryloxy, arylthio, arylsulfonyl or aroyl;
- X 18 represents O, S, CH 2 , a single covalent bond or -C ⁇ C-;
- Y 39 represents halogen, polyhaloalkoxy, polyhaloalkyl. cyano, alkylsulfonyl, alkylsulfonyloxy, polyhaloalkylsulfonyl or polyhaloalkylsulfonyloxy; and Y 40 represents haloalkyl, polyhaloalkyl, alkoxy provided that X 18 is not S or a single covalent bond; polyhaloalkoxy, cyano, alkylthio provided that X 18 is not 0 or a single covalent bond; alkylsulfonyl, nitro, dialkoxyphosphinyl or trialkylammonium;
- Y 41 is the same or different and represents halogen
- Y 42 is the same or different and represents halogen, alkoxy, alkylthio or polyhaloalkoxy:
- Y 52 and Y 53 are independently halogen; g is a value of from 0 to 5 inclusive;
- X 20 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -CH 2 O-, -CH 2 -, -C(halogen) 2 , -OCH 2 O-, -OCH 2 CH 2 O- or -C ⁇ C- provided that g is a value of at least 1;
- R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
- Y 44 are independently O or S
- R 35 represents an unsubstituted or substituted heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4,-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothizole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, isoquinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzofuran, dibenzothiophene, benzox
- X 21 represents O, S or NH provided that when X 21 is NH then R 35 is not pyridine, and when X 21 is S then R 35 is not unsubstituted benzothiazole;
- Y 45 and Y 46 are independently halogen
- R 37 and R 38 independently represent halogen, nitro, cyano, polyhaloalkyl, polyhaloalkoxy, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, alkoxycarbonyl, polyhaloalkylsulfonyl or R 39 -X 22 - Provided that only one of R 37 and R 38 may be R 39 -X 22 - at any one time;
- R 39 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X 22 represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, -CH 2 S-,
- Y 47 represents halogen
- B 14 represents O, S, NH or N R 40 wherein
- R 40 represents alkyl, alkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylamino, aroyl or arylsulfonyl; provided that (i) when B 14 is
- R 39 - , R 39 -alkyl- R 39 -C( O)- ,
- R 37 and R 38 are other than R 39 - X 22 -; (ii) when B 14 is other than R 39 - , R 39 -alkyl- ,
- R 41 and R 42 independently represent halogen or R 43 - X 23 - provided that only one of
- R 41 and R 42 may be R 43 - X 23 - at any one time;
- R 43 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl
- X 23 represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, CH 2 S-,
- B 15 represents O, S, NH or N R 44 wherein
- R 44 represents alkyl, alkylsulfonyl, polyhaloalkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl; unsubstituted or substituted aryl, aralkyl, aryloxy, arylamino, aroyl or arylsulfonyl; provided that when R 15 is
- R 41 and R 42 are other than R 43 -X 23 -; and further provided that when B 15 is other than
- R 45 , R 46 , R 47 , and R 48 independently represent hydrogen, halogen, nitro, cyano, polyhaloalkyl, polyhaloalkoxy, alkylsulfonyl, polyhaloalkylsulfonyl, acyl, alkylthio, alkyl, alkoxy, alkylsulfinyl or R 49 -X 24 - provided that one of R 45 , R 46 , R 47 , and R 48 is
- R 47 and R 48 include no more than two of hydrogen, alkyl or alkoxy at any one time;
- R 49 represents unsubstituted or substituted phenyl, 1- or 2-naphthyl or heteroaryl;
- X represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, -CH 2 S-,
- Y 48 represents halogen
- B 16 represents O, S or NH
- R 50 represents an unsubstituted or substituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated;
- Y 54 and Y 55 are independently halogen
- R 51 represents or unsubstituted or substituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated;
- B 19 represents -CH 2 - or -CH(alkyl)-; and i is a value of 0 or 1;
- Y 56 and Y 57 are independently halogen
- B 20 represents -CH 2 C(CH 3 ) 4 SCH 2 -
- -CH 2 CH C(CH 3 )OCH 2 -, -CH 2 CH 2 SCH 2 CH(CH 3 )-,
- R 52 represents hydrogen, alkenyl; unsubstituted or substituted aryl or alkaryl;
- Y 58 and Y 59 are independently halogen
- X 25 represents O, S, NH, CH 2 -CH 2 O- or a single covalent bond
- R 54 is the same or different and is one or more hydrogen, halogen, alkyl, aryl, aralkyl, alkenyl, alkynyl, polyhaloalkyl, NH 2 , NH(alkyl),
- N(alkyl) 2 alkoxy, polyhaloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, aralkoxy, CO 2 alkyl,
- X 26 represents O, S, SO, SO 2 , CH 2 , a single covalent bond, -CH 2 O-, -CH 2 S-,
- Y 50 and Y 51 are the same or different and are halogen
- R 68 represents unsubstituted or substituted phenyl or 1- or 2-naphthyl
- X 27 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -C(halogen) 2 , -OCH 2 O-, -OCH 2 CH 2 O-, -CH 2 O-, -C ⁇ C-, -OCH(alkyl)-,
- R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
- Y 44 are independently O or S
- Z 1 and Z 2 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl: and
- Y 67 and Y 68 are the same or different and represent hydrogen,halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino;
- R 69 represents unsubstituted or substituted phenyl or 1- or 2-naphthyl
- X 28 is NH, CH 2 or a covalent bond
- Z 3 and Z 4 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
- Y 69 and Y 70 are the same or different and represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylammo, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino, with the proviso that Y 69 and Y 70 taken together do not represtt eeiitthheerr the same halogen or halogen and hydrogen;
- R 70 represents an unsubstituted or substituted, unsaturated or saturated, aromatic or non-aromatic heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4,-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothizole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, isoquinoline, quinazoline, phthalazine, benzopyridazine, benzopyrazine, carbazole, dibenzo
- X 29 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -CH 2 O-, -CH 2 -, a covalent bond, -C(halogen) 2 , -OCH 2 O-,
- R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
- Y 44 are independently O or S;
- Z 5 and Z 6 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl , aryl, aralkyl , alkenyl or alkynyl ; and
- Y 71 and Y 72 are the same or different and represent hydrogen, halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, amino, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, alkoxycarbonyl, alkylaminocarbonyl, aminocarbonyl, dialkylaminocarbonyl, dialkylaminosulfonyl, alkylaminosulfonyl, .aminosulfonyl, dialkoxyalky
- R 71 represents unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicycloalkyl, bicycloalkenyl, bicycloalkadienyl, tricycloalkyl, tricycloalkenyl or tricycloalkadienyl:
- X 30 represents -CH(alkyl)O-, -C(alkyl) 2 O-, -OCH 2 -, -CH 2 O-, -CH 2 -, a covalent bond, -C(halogen) 2 , -OCH 2 O-, -OCH 2 CH 2 O-, -C ⁇ C-, -OCH(alkyl)-, -OC(alkyl) 2 , -OCH(alkyl)O-, -OC(alkyl) 2 O-, -OCH(alkyl)CH 2 O-, -OCH(alkyl)CH(alkyl)O-, -CH(alkyl)CH(alkyl)-, -CH(alkyl)-, -C(alkyl) 2 -, -CH 2 CH 2 O-, -OCH 2 CH 2 -, -CH(alkyl)CH 2 O-, -CH 2 CH 2 -, -CH(CN)O
- R 34 represents acyl, alkylsulfonyl, polyhaloalkyl, polyhaloacyl, polyhaloalkylsulfonyl or unsubstituted or substituted aroyl or arylsulfonyl and Y 43 and
- Y 44 are independently O or S;
- Z 7 and Z 8 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
- Y 73 and Y 74 are the same or different and represent hydrogen,halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, aryl, polyhaloalkylsulfonyl, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy and polyhaloalkylsulfonyloxy;
- B 21 represents -CH 2 C(CH 3 ) 2 SCH 2 -
- R 52 represents hydrogen, alkenyl; unsubstituted or substituted aryl or alkaryl; Z 9 and Z 10 are independently O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
- Y 75 and Y 76 are the same or different and represent hydrogen,halogen, alkyl, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, amino, alkylamino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino;
- R 72 represents unsubstituted or substituted phenyl or 1- or 2-naphthyl
- X 31 represents -OCH 2 -, -CH 2 -, a covalent bond, -C(halogen) 2 , -C ⁇ C-, -OCH(alkyl)-,
- h is a value of from 0 to 2 inclusive
- Z 11 represents O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
- Y 77 , Y 78 and Y 79 are the same or different and represent hydrogen,halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, aIkylamino, amino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino, with the proviso that when Y 77 is halogen and
- Y 79 is hydrogen then Y 78 cannot be amino, alkylamino, dialkylamino or acylamino and with the further proviso that when Y 77 and Y 78 are the same halogen then Y 79 cannot be hydrogen or hydroxy;
- R 73 represents an unsubstituted or substituted, unsaturated or saturated, aromatic or non-aromatic heterocyclic ring system selected from isoxazole, isothiazole, pyrazole, imidazole, 1,2,4-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4,-thiadiazole, 1,3,4-thiadiazole, oxazole, thiazole, benzopyrazole, benzimidazole, benzoxazole, benzothizole, indole, pyrrole, furan, thiophene, benzofuran, benzothiophene, pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, quinoline, isoquinoline, quinazo ⁇ ine, phthalazine, benzopyridazine, benzopyrazine, carbazole, di
- X 32 represents -OCH 2 -, -CH 2 -, a covalent bond, -C(halogen) 2 , -C ⁇ C-, -OCH(alkyl)-, -OC(alkyl) 4 , -CH(alkyl)CH(alkyl)-, -CH(alkyl)-,
- h is a value of from 0 to 2 inclusive
- Z 12 represents O, S, C 1 -C 8 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl; and
- Y 80 , Y 81 and Y 82 are the same or different and represent hydrogen,halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, alkylamino, amino, dialkylamino, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfonyloxy, polyhaloalkylsulfonyloxy, phosphono or phosphino;
- R 74 represents unsubstituted or substituted alkyl, alkenyl, alkynyl, cyploalkyl cycloalkenyl, cycloalkadienyl, cycloalkatrienyl, bicycloalkyl, bicycloalkenyl, bicycloalkadienyl, tricycloalkyl, tricycloalkenyl or tricycloalkadienyl;
- X 33 represents -OCH 2 -, -CH 2 -, a covalent bond, -C(halogen) 2 , -C ⁇ C-, -OCH(alkyl)-, -OC(alkyl) 2 , -CH(alkyl)CH(alkyl)-, -CH(alkyl)-,
- h is a value of from 0 to 2 inclusive
- Z 13 represents O, S, H 2 -H 2 alkylidene, substituted or unsubstituted benzylidene, NH or NR''' wherein R''' is alkyl, aryl, aralkyl, alkenyl or alkynyl: and Y 83 , Y 84 and Y 85 are the same or different and represent hydrogen, halogen, alkyl, hydroxy, cyano, polyhaloalkyl, alkoxy, polyhaloalkoxy, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro, acyl, polyhaloalkylsulfonyl, alkylamino, amino, dialkylammo, acylamino, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkenylsulfonyloxy, haloalkylsulfon
- Y 62 , Y 63 , Y 64 , Y 65 and Y 66 are the same or different and are halogen;
- R 1 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formaraidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhalo
- R 1 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylammocarbonyl, diaIkylaminocarbony
- X is a covalent single bond or double bond, a substituted or unsubstituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, al
- R 36 is a substituted or unsubstituted, asymmetrical heterocyclic ring system having at least three nitrogen atoms which are selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxys
- R 3 is a substituted or unsubstituted, carbocyclic or heterocyclic ring system selected from a monocyclic aromatic or nonaromatic ring system, a bicyclic aromatic or nonaromatic ring system, a polycyclic aromatic or nonaromatic ring system, and a bridged ring system which may be saturated or unsaturated in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhalo
- R 3 is a substituted heteroatom or substituted carbon atom, or a substituted or unsubstituted, branched or straight chain containing two or more carbon atoms or heteroatoms in any combination in which the permissible substituents are the same or different and are one or more hydrogen, halogen, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,
- Y 1 and Y 4 are independently oxygen or sulfur
- Y 2 and Y 3 are independently oxygen, sulfur, amino or a covalent bond
- R 4 and R 5 are independently hydrogen or substituted or unsubstituted alkyl, polyhaloalkyl, phenyl or benzyl in which the permissible substituents are the same or different and are one or moris hydrogen, halogen, alkylcarbonyl , alkylcarbonylalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkylthio, polyhaloalkenylthio, thiocyano, propargylthio, hydroxyimino, alkoxyimino, trialkylsilyloxy, aryldialkylsilyloxy, triarylsilyloxy, formamidino, alkylsulfamido, dialkylsulfamido, alkoxysulfonyl, polyhaloalkoxysulfonyl, hydroxy, amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylamin
- the heterocyclic nitrogen-containing compounds encompassed within formula 1 can be prepared by conventional methods known in the art, and many may be available from various suppliers.
- the novel heterocyclic nitrogen-containing compounds of formulae (i) through (xxxiii) above which may be used in the method of this invention can be prepared by reacting appropriate starting ingredients in accordance with conventional procedures described in the art as illustrated below.
- novel heterocyclic nitrogen-containing compounds of formula (i) can be prepared by the following general reaction scheme:
- R 24 , X 10 , a, j and Y 19 are as defined hereinabove.
- Reactions of this general type for preparing substituted pyridines including process conditions are described for example by Mertel, H.E., The Chemistry of Heterocyclic Compounds, Pyridine and Derivatives-Part Two, Halopyridines, P. 351, Interscience, Wiley, New York (1961). Intermediates such as 2,4,6-trichloropyridine are described in U.S. Patent 3.830,820.
- other preparation methods for the novel compounds of formula (i) are described in Fuson. R.C., Advanced Organic Chemistry, p. 124, Wiley, New York (1950), and Ochiai, E., Aromatic Amine Oxides, p. 21, Elsevier, New York (1967).
- novel heterocyclic nitrogen-containing compounds of formula (ii) can be prepared by the following general reaction scheme:
- R 25 , X 11 , b and Y 20 are as defined hereinabove. Reactions of this general type for preparing substituted pyrazines including process conditions are described for example in U.S. Patent 4.254,125.
- novel heterocyclic nitrogen-containing compounds of formula (iii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (v) can be prepared by the following general reaction scheme:
- R 28 , X 14 , Y 27 , Y 28 and Y 29 are as defined hereinabove.
- Reactions of this general type for preparing 5-substituted pyrimidines including process conditions and intermediate preparations are described for example by Fieser, L.F. and Fieser, M., Organic Chemistry, p. 310, Heath, Boston (1972) also Brown, D.J., The Pyrimidines; The Chemistry of Heterocyclic Compounds, pp. 50, 166, Interscience, Wiley, New York (1962).
- the novel heterocyclic .nitrogen-containing compounds of formula (vi) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (vii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (viii) can be prepared by the following general reaction scheme:
- 1,3,5-triazines including process conditions and intermediate preparations are described for example in German Patent 952,478, U.S. Patent 2,824,823.
- R 32 , f, X 18 , Y 39 , Y 40 and Y 49 are as defined hereinabove.
- Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are described for example in U.S. Patent 3,316,264.
- Intermediates such as 2,4-dichloro-6-(diethoxyphosphinyl)-1,3,5-triazine are described in Japan Patent 74 46635.
- Other preparation methods for the novel compounds of formula (ix) are described in Mendoza, C.E. et al., J. Ag. Food Chem., 19, (1), 41-45 (1972).
- novel heterocyclic nitrogen-containing compounds of formula (x) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xi) can be prepared by the following general reaction scheme:
- R 33 , g, X 20 , Y 52 , Y 53 and Y 49 are as defined hereinabove.
- Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
- Other preparation methods for the novel compounds of formula (xi) are described in Allen, C.F.H. and Converse, S., Org. Syn. Coll., Vol. I, 226-227, U.S. Patent 1,911,689, Bessiere-Chretien, Y. and Serne, H., Bull. Soc. Chim. France. (6).
- novel heterocyclic nitrogen-containing compounds of formula (xii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xiii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xiv) can be prepared by the following general reaction scheme:
- R 37 , R 38 , B 14 and Y 47 are as defined hereinabove.
- Reactions of this general type for preparing substituted azoles including process conditions and intermediate preparations are described in Pahanayak, B.K., J. Ind. Chem. Soc., 55, (3), 264-267 (1978) and Young. T.E. and Amstutz, E.D., J. Amer. Chem. Soc., 73, 4773-4775. (1951).
- Other preparation methods for the novel compounds of formula (xiv) are described by Tripathi, H. et al., Agric. Biol. Chem., 37, 1375 (1973) and Young, T.E. and Amstutz, E.D., J. Amer. Chem. Soc. 73, 4773-4775 (1951).
- novel heterocyclic nitrogen-containing compounds of formula (xv) can be prepared by the following general reaction scheme:
- R 41 , R 42 , and B 15 are as defined hereinabove.
- Reactions of this general type for preparing substituted 1,2,4-azoles including process conditions and intermediate preparations are described by Selim, M. and Selim, M. , Bull. Soc. Chim. France. 1219-1220 (1967).
- novel heterocyclic nitrogen-containing compounds of formula (xvi) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xvii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xviii) can be prepared by the following general reaction scheme:
- R 50 , B 17 , Y 54 , Y 55 and Y 49 are as defined hereinabove.
- Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
- Other preparation methods for the novel compounds of formula (xix) are described by Beech, W.F., J. Chem. Soc., (C), 466-472 (1967).
- novel heterocyclic nitrogen-containing compounds of formula (xx) can be prepared by the following general reaction scheme:
- 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
- novel heterocyclic nitrogen-containing compounds of formula (xxi) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xxii) can be prepared by "the following general reaction scheme:
- R 53 , X 25 , Y 60 , Y 61 and Y 49 are as defined hereinabove. Reactions of this general type for preparing substituted 1,3,5-triazines including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (viii) above.
- novel heterocyclic nitrogen-containing compounds of formula (xxiii) can be prepared by the following general reaction scheme:
- R 54 , X 26 , Y 50 and Y 51 are as defined hereinabove. Reactions of this general type for preparing hexahydro-1,3,5-triazines including process conditions are described for example by
- novel heterocyclic nitrogen-containing compounds of formula (xxiv) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xxvi) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xxvii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xxviii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xxix) can be prepared by the following general reaction scheme:
- Suitable halogenating agents include, for example, PCL 5 , POCl 3 , PBr 5 and POBr 3 and mixtures thereof.
- Reactions of this general type for preparing substituted pyridazinones including process conditions and intermediate preparations are described for example in Yuki Gosei Kagaku Kyotai Shi 28, (4), 462-463 (1970).
- Other preparation methods for the novel compounds of formula (xxix) are described in Yakugaku Zasshi 86, (12), 1168-1172 (1966), Acta Dol. Pharm.
- novel heterocyclic nitrogen-containing compounds of formula (xxx) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xxxi) can be prepared by the following general reaction scheme:
- R 74 , X 33 , Z 13 , Y 83 , Y 84 AND Y 85 are as defined hereinabove. Reactions of this general type for preparing substituted pyridazinones including process conditions and intermediate preparations are similar to the procedures employed for preparing compounds of formula (xxix) above.
- novel heterocyclic nitrogen-containing compounds of formula (xxxii) can be prepared by the following general reaction scheme:
- novel heterocyclic nitrogen-containing compounds of formula (xxxiii) can be prepared by the following general reaction scheme:
- the antitranspirant compounds of formula 1 have been found to significantly reduce plant and crop usage of water, i.e., reduce transpiration rate, and increase the resistance of plant leaf surfaces to the loss of moisture vapor, i.e., increase diffusive resistance.
- the antitranspirant compounds used in this invention are substantially non-inhibiting of photosynthetic light-requiring reactions, substantially non-phytotoxic to growing plants and serve to increase crop yields in comparison with untreated crops at similar conditions, especially in regions where plants are subject to moisture stress conditions.
- the antitranspirant compounds used in this invention provide for the conservation of soil moisture by reducing plant and crop usage of water during certain development periods, e.g., vegetative period, thereby making the unused water available at other periods of plant or crop development, e.g., reproductive growth period.
- stomata are minute openings in the epidermis of plant leaf surfaces through which occurs gaseous interchange between the atmosphere and the intercellular spaces within the leaf. It is believed that the antitranspirant compounds of formula 1 effectively reduce the transpiration rate in plants by closing plant stomata or constricting plant stomatal openings to such a degree that moisture loss is reduced and, in addition, the compounds exhibit substantially no detrimental effect on photosynthetic electron flow.
- the photosynthetic process in plants consists of light-requiring reactions, i.e., light reactions, and non-light-requiring reactions, i.e., dark reactions.
- the dark reactions in general involve a complex of enzyme-mediated reactions which provide for the conversion of carbon dioxide to sugar.
- Photosystem I and Photosystem II Two light-requiring reactions are involved in plant photosynthesis and are conventionally termed Photosystem I and Photosystem II. See. for example, Salisbury. F.B. and Ross, C.W., Plant Physiology, pp. 131-135 (1978). These photosystems are interconnected by an electron transport chain, and provide reducing power and chemical energy to the dark reactions. Inhibition of either or both of these photosystems can detrimentally affect photosynthesis, thereby causing plant injury or even plant death.
- the antitranspirant compounds used in this invention have been found to cause no or substantially no inhibition of Photosystem I or Photosystem II.
- the herbicide atrazine is known to substantially inhibit the light reactions of photosynthesis, particularly the electron transport chain. See, for example, Jachetta, J.J. and Radosevich, S.R., Weed Science 29: 37-43 (1981).
- Such herbicidal inhibition leads to a buildup of carbon dioxide within the leaf which causes closure of the stomates.
- the antitranspirant activity of atrazine is associated with its herbicidal properties.
- substantially no inhibition of photosynthetic electron transport refers to no or little inhibition of photosynthetic electron transport.
- an effective amount of a heterocyclic nitrogen-containing compound for reducing moisture loss from plants refers to an antitranspirationally effective amount of the compound sufficient to reduce transpirational moisture loss from plants without substantially inhibiting plant photosynthetic electron transport.
- an effective amount of a heterocyclic nitrogen-containing compound for increasing crop yield refers to a yield enhancing effective amount of the compound sufficient to increase crop yield without sustantially inhibiting plant photosynthetic electron transport.
- the effective amount of compound can vary over a wide range depending on the particular compound employed, the particular crop to be treated, environmental and climatic conditions, and the like, provided that the amount of compound used does not cause substantial inhibition of plant photosynthetic electron transport or substantial phytotoxicity, e.g., foliar burn, chlorosis or necrosis, to the plant.
- the compound can preferably be applied to plants and crops at a concentration of from about 0.25 to 15 pounds of compound per acre as more fully described below.
- heterocyclic nitrogen-containing compounds contemplated by formula 1 may be employed according to a variety of conventional methods known to those skilled in the art.
- Compositions containing the compounds as the active ingredient will usually comprise a carrier and/or diluent, either liquid or solid.
- Suitable liquid diluents or carriers include water, petroleum distillates, or other liquid carriers with or without surface active agents.
- Liquid concentrates may be prepared by dissolving one of these compounds with a nonphytotoxic solvent such as acetone, xylene, nitrobenzene, cyclohexanone or dimethylformamide and dispersing the active ingredients in water with the aid of suitable surface active emulsifying and dispersing agents.
- dispersing and emulsifying agents are dictated by the nature of the composition and the ability of the agent to facilitate the dispersion of the active ingredient. Generally, it is desirable to use as little of the agent as is possible, consistent with the desired dispersion of the active ingredient in the spray so that rain does not re-emulsify the active ingredient after it is applied to the plant and wash it off the plant.
- Nonionic, anionic. or cationic dispersing and emulsifying agents may be employed, for example, the condensation products of alkylene oxides with phenol and organic acids, alkyl aryl sulfonates, complex ether alcohols, quaternary ammonium compounds, and the like.
- the active ingredient is dispersed in and on an appropriately divided solid carrier such as clay, talc, bentonite, diatomaceous earth, fuller's earth, and the like.
- an appropriately divided solid carrier such as clay, talc, bentonite, diatomaceous earth, fuller's earth, and the like.
- the aforementioned dispersing agents as well as lignosulfonates can be included.
- the required amount of the active ingredient contemplated herein may be applied per acre treated in from 1 to 200 gallons or more of liquid carrier and/or diluent or in from about 5 to 500 pounds of inert solid carrier and/or diluent.
- concentration in the liquid concentrate will usually vary from about 5 to 95 percent by weight and in the solid formulations from about 0.5 to about 90 percent by weight.
- Satisfactory sprays or dusts for general use contain from about 0.1 to about 100 pounds of active ingredient per acre, preferably from about 0.25 to about 15 pounds of active ingredient per acre, and more preferably from about 0.5 to about 5 pounds of active ingredient per acre.
- Formulations useful in the conduct of this invention can also contain other optional ingredients such as stabilizers or other biologically active compounds, insofar as they do not impair or reduce the activity of the active ingredient and do not harm the plant being treated.
- Other biologically active compounds include, for example, one or more insecticidal, herbicidal, fungicidal, nematicidal, miticidal, plant growth regulators or other known compounds. Such combinations may be used for the known or other purpose of each ingredient and may provide a synergistic effect.
- the antitranspirant compounds of formula l. are preferably applied to plants and crops under substantially little or no water stress conditions, or what can be considered as average or normal growing conditions.
- a preferred condition for compound application is prior to substantial soil moisture loss. While not wishing to be bound to any particular theory, it is believed that application of the antitranspirant compounds does not result in a reduction of the minimum total water requirements of a treated plant or crop, but rather the application of such compounds serves to promote more efficient water utilization by treated plants and crops.
- the antitranspirant effect does not reduce the total amount of water needed to grow a given plant or crop except for water savings which may be realized for some crops under irrigation, but rather such antitranspirant effect is manifested by an increase in yield of treated crops having no or limited irrigation and rainfall in comparison with untreated crops at similar conditions.
- the antitranspirant compounds of formula 1 are preferably applied to plants and crops under conditions which favor large gradients in water vapor pressure between the saturated atmosphere within the leaf and the atmosphere around the leaf. Such conditions include low atmospheric humidity, high light/heat loads on the leaf, and high rates of air movement.
- the application of the antitranspirant compounds of formula 1 to plants reduces the amount of water utilized by the plane for on the order of about a 1 to 6 week period and therefore provides for a greater amount of reserve water available in the soil during other developmental periods such as the critical reproductive growth phase.
- This soil moisture conservation can minimize any water deficit within plant tissues during critical developmental periods such as the reproductive growth phase resulting in increased crop yield.
- the antitranspirant compounds used in this invention may likewise be applied during the plant reproductive growth phase to obtain similar results.
- the antitranspirant compounds of formula 1 are useful for decreasing irrigation water requirements especially in dry climate regions, for protecting plants from wilting or other damage during transplantation or shipment or during severe cold weather, and for alleviating water stress in certain types of environments as indicated above.
- Such compounds are useful in agriculture, horticulture and related fields and can be applied to vegetation such as non-deciduous ornamental shrubs, evergreens, trees, and the like, to protect them against winter kill.
- a chief cause of winter kill is an excessive loss of moisture from leaf surfaces on sunny or windy days when the ground is frozen and the root systems cannot replace the water loss.
- the antitranspirant compounds can also be applied to other ornamentals such as roses and other flowers, Christmas trees, and the like, to preserve freshness and retard needle drop.
- the antitranspirant compounds can further be used in avoiding or minimizing the effects of summer scald and transplant shock.
- antitranspirant compounds of formula 1 may also be used to control foliar diseases on crops such as wheat and oats. See, for example, Avant Gardener, Vol. 18, No. 1, November, 1985, in which antitranspirants are used to control fungus diseases.
- plants refer in general to any agronomic or horticultural crops, ornamentals and turfgrasses.
- Illustrative of plants which may be treated by the antitranspirant compounds of formula 1 according to the method of this invention include, for example, corn, cotton, sweet potatoes, white potatoes, alfalfa, wheat, rye, upland rice, barley, oats, sorghum, dry beans, soybeans, sugar beets, sunflowers, tobacco, tomatoes, canola, deciduous fruit, citrus fruit, tea, coffee, olives, pineapple, cocoa, banana, sugar cane, oil palm, herbaceous bedding plants, woody shrubs, turfgrasses, ornamental plants, evergreens, trees, flowers, and the like.
- crops refer in general to any of the illustrative agronomic or horticultural crops above.
- Transplanted stock refers in general to tobacco, tomatoes, eggplant, cucumbers, lettuce, strawberries, herbaceous bedding plants, woody shrubs, tree seedlings and the like.
- the antitranspirant compounds contemplated herein reduce transpirational moisture loss from plants and increase crop yields.
- Such compounds have a high margin of safety in that when used in sufficient amount to provide an antitranspirant effect or yield enhancing effect, they do not inhibit plant photosynthetic electron transport or burn or injure, the plant, and they resist weathering which includes wash-off caused by rain, decomposition by ultraviolet light, oxidation, or hydrolysis in the presence of moisture or, at least, such decomposition, oxidation, and hydrolysis as would materially decrease the desirable antitranspirant characteristic of the active ingredient or impart undesirable characteristics, for instance, phytotoxicity, to the active ingredients.
- Mixtures of the active compounds may be employed if desired as well as combinations of the active compounds with other biologically active compounds or ingredients as indicated above.
- Compound 48 This compound is referred to hereinafter as Compound 48.
- Example VIII In a manner similar to Example VIII, 4.63 grams (0.04 mole) of 2-chloroaniline and 6.69 grams (0.04 mole) of cyanuric chloride were reacted in the presence of 3.89 grams (0.04 mole) of 2,6-lutidine except that the cooling bath was removed at the end of the feed period and the stirred mixture allowed to warm to room temperature. After filtering off lutidine hydrochloride, the filtrate was freed of acetone solvent under reduced pressure and the resulting solid was crystallized from a mixture of hexane and benzene.
- This compound is referred to hereinafter as Compound 66.
- Example XIV Into a solution containing 600 milligrams (0.002 mole) of 4,6-dichloro-2-(4'-nitrophenylamino)-1,3,5-triazine prepared in Example XIV in 300 milliliters of CH 2 Cl 2 was bubbled HBr gas at room temperature for a period of 4 hours. The resulting mixture was stored in a refrigerator for about 48 hours and an oil, which separated from CH 2 Cl 2 , was collected by decantation.
- This compound is referred to hereinafter as Compound 67.
- This compound is referred to hereinafter as Compound 68.
- Compound 70 This compound is referred to hereinafter as Compound 70.
- This compound is referred to hereinafter as Compound 71.
- This compound is referred to hereinafter as Compound 73.
- Part B Preparation of 2,4-dichloro-6- (4'-sec-butyloxyphenoxy)-1,3,5-triazine Into a 100 mill iliter 3-necked round bottom f lask equipped with a thermometer, addition funnel and nitrogen inlet was added cyanuric chloride (2.22 grams, 0.01 mole) dissolved in 20 milliliters of acetone. After cooling to a temperature of 0-5oC, 4-(sec-butyloxy) phenol (2.0 grams, 0.01 mole) prepared in Part A and 2,6-lutidine (1.40 milliliters, 0.01 mole) dissolved in 20 milliliters of acetone were slowly added dropwise via the addition funnel.
- the temperature of the reaction was maintained between 0-5oC during the addition.
- the reaction mixture was then stirred at room temperature for a period of 16 hours. After this period, the reaction mixture was filtered through a Celite pad and the pad rinsed with acetone. Ice-water was added and the oil which precipitated was extracted with EtOAc. The EtOAc layers were washed with water, dried (MgSO 4 ) and cpncentrated to give a brown semi-solid.
- This compound is referred to hereinafter as Compound 74.
- Example XXIV Into a solution containing 2.0 grams (0.007 mole) of 4-chloro-6-methyl-2-(2',4'-dichlorophenoxy)-1,3,5-triazine prepared in Example XXIV in 300 milliliters of CH 2 Cl 2 was bubbled dry HBr gas for a period of 3 hours. The mixture was allowed to stand at room temperature for about 18 hours. The suspension was then filtered and the solids partitioned between NaHCO solution and CH 2 Cl 2 .
- This compound is referred to hereinafter as Compound 88.
- Example XXVIII The column chromatography fractions from Example XXVIII were examined and a group identified as containing 4-chloro-6-(2',2',2'-trifluoroethoxy)-2-phenyl-1,3,5-triazine as a second component. These were combined and purified by preparative liquid chromatography (silica gel) using 10% ethyl acetate in hexane as the eluent to give 320 milligrams (0.001 mole) of 4-chloro-6-(2',2',2'-trifluoroethoxy)-2-phenyl-1,3,5-triazine as an oil. Elemental analysis of the product indicated the following:
- Compound 90 This compound is referred to hereinafter as Compound 90.
- This compound is referred to hereinafter as Compound 92.
- Example XXXII In a manner similar to that employed in Example XXXII, other compounds were prepared.
- reaction mixture was then diluted with 150 milliliters of water and extracted with CH 2 Cl 2
- 2,4-Dichlorobenzaldehyde oxime prepared in Part A was reacted with cyanuric chloride using a procedure similar to that described in Example XXXII above.
- the reaction mixture was filtered to remove the precipitate and the filtrate was poured onto ice causing a yellow solid to form.
- the solid was separated and recrystallized from acetone-water to yield 2.1 grams (0.006 mole) of 2,4-dichlorobenzaldehyde O-(4, 6-dichloro-1,3,5-triazin- 2-yl)oxime as pale yellow needles having a melting point of 124°C-124.5°C. Elemental analysis of the product indicated the following:
- This compound is referred to hereinafter as Compound 96.
- the compound is referred to hereinafter as Compound 97.
- This compound is referred to hereinafter as Compound 98.
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Application Number | Priority Date | Filing Date | Title |
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US82438986A | 1986-01-23 | 1986-01-23 | |
US824389 | 1986-01-23 | ||
US93941686A | 1986-12-15 | 1986-12-15 | |
US939416 | 1986-12-15 |
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EP87901826A Withdrawn EP0258391A1 (en) | 1986-01-23 | 1987-01-23 | Use of heterocyclic nitrogen-containing compounds for reducing moisture loss from plants and increasing crop yield |
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EP (1) | EP0258391A1 (pt) |
KR (1) | KR880700635A (pt) |
AU (1) | AU7031687A (pt) |
DK (1) | DK496187A (pt) |
FI (1) | FI874111A0 (pt) |
GR (1) | GR870094B (pt) |
IL (1) | IL81307A0 (pt) |
OA (1) | OA08675A (pt) |
PT (1) | PT84183B (pt) |
TN (1) | TNSN87008A1 (pt) |
WO (1) | WO1987004321A2 (pt) |
ZW (1) | ZW1287A1 (pt) |
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WO1996004278A1 (fr) * | 1994-08-02 | 1996-02-15 | Nippon Soda Co., Ltd. | Derive d'oxazole, son procede de production et herbicide |
HUP9901155A3 (en) | 1996-02-13 | 2003-04-28 | Astrazeneca Ab | Quinazoline derivatives as vegf inhibitors |
DE69709319T2 (de) | 1996-03-05 | 2002-08-14 | Astrazeneca Ab, Soedertaelje | 4-anilinochinazolin derivate |
GB9707800D0 (en) | 1996-05-06 | 1997-06-04 | Zeneca Ltd | Chemical compounds |
GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
CA2263479A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Quinoline derivatives inhibiting the effect of growth factors such as vegf |
AU8816298A (en) | 1997-08-22 | 1999-03-16 | Zeneca Limited | Oxindolylquinazoline derivatives as angiogenesis inhibitors |
PT1119567E (pt) | 1998-10-08 | 2005-08-31 | Astrazeneca Ab | Derivados de quinazolina |
AU763618B2 (en) | 1999-02-10 | 2003-07-31 | Astrazeneca Ab | Quinazoline derivatives as angiogenesis inhibitors |
GB9910580D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
GB9910579D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
SK287401B6 (sk) | 1999-11-05 | 2010-09-07 | Astrazeneca Ab | Deriváty chinazolínu, spôsob ich prípravy, farmaceutická kompozícia, ktorá ich obsahuje, a ich použitie |
DE60121931T2 (de) | 2000-04-07 | 2007-03-01 | Astrazeneca Ab | Chinazolinverbindungen |
DE60137234D1 (de) | 2000-08-09 | 2009-02-12 | Astrazeneca Ab | Cinnoline verbindungen |
JP2004505964A (ja) | 2000-08-09 | 2004-02-26 | アストラゼネカ アクチボラグ | Vegf阻害活性を有するキノリン誘導体 |
US20030078347A1 (en) * | 2001-08-28 | 2003-04-24 | General Electric Company | Triazine compounds, polymers comprising triazine structural units, and method |
BR0307151A (pt) | 2002-02-01 | 2004-12-07 | Astrazeneca Ab | Composto ou um sal do mesmo, processo para a preparação do mesmo, composição farmacêutica, uso do composto ou de um seu sal, método para produzir um efeito antiangiogênico e/ou redutor da permeabilidade vascular em um animal de sangue quente, como um ser humano, que necessita de um tratamento do tipo referido, e, processos para a preparação de 5-bromo-7- azaindol, e para a produção de 5-metóxi-7-azaindol |
GB0330002D0 (en) | 2003-12-24 | 2004-01-28 | Astrazeneca Ab | Quinazoline derivatives |
JPWO2007010731A1 (ja) | 2005-07-15 | 2009-01-29 | Jsr株式会社 | 含窒素芳香族化合物およびその製造方法、重合体およびプロトン伝導膜 |
US8084454B2 (en) * | 2007-04-11 | 2011-12-27 | Canbas Co., Ltd. | Compounds with anti-cancer activity |
KR101741415B1 (ko) * | 2009-04-29 | 2017-05-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR20120125270A (ko) | 2010-02-02 | 2012-11-14 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 트리아진-기재 기록 단량체를 갖는 광중합체 배합물 |
WO2014122669A1 (en) | 2013-02-07 | 2014-08-14 | Subramanyam Sundaresan | A total foliar product for agriculture / horticulture / tissue culture and hydroponic cultivation |
CN103290678B (zh) * | 2013-04-13 | 2015-07-22 | 徐茂航 | 一种用于纺织品抗菌整理剂 |
US10435365B2 (en) | 2014-03-16 | 2019-10-08 | Hadasit Medical Research Services And Development Ltd. | Type III deiodinase inhibitors and uses thereof |
EA202190847A1 (ru) | 2018-09-27 | 2021-06-23 | Фмк Корпорейшн | Промежуточные продукты для получения гербицидных пиридазинонов |
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GB1419632A (en) * | 1972-04-11 | 1975-12-31 | Ici Ltd | Hydroxyphenoxy-s-triazine derivatives |
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- 1987-01-22 PT PT84183A patent/PT84183B/pt not_active IP Right Cessation
- 1987-01-23 TN TNTNSN87008A patent/TNSN87008A1/fr unknown
- 1987-01-23 WO PCT/US1987/000240 patent/WO1987004321A2/en not_active Application Discontinuation
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- 1987-01-23 AU AU70316/87A patent/AU7031687A/en not_active Abandoned
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- 1987-09-21 FI FI874111A patent/FI874111A0/fi not_active IP Right Cessation
- 1987-09-22 KR KR870700857A patent/KR880700635A/ko not_active Application Discontinuation
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AU7031687A (en) | 1987-08-14 |
PT84183A (pt) | 1987-02-01 |
OA08675A (fr) | 1989-03-31 |
FI874111A (fi) | 1987-09-21 |
KR880700635A (ko) | 1988-04-11 |
TNSN87008A1 (fr) | 1990-01-01 |
GR870094B (en) | 1988-09-28 |
WO1987004321A3 (en) | 1987-11-05 |
DK496187D0 (da) | 1987-09-22 |
IL81307A0 (en) | 1987-08-31 |
PT84183B (pt) | 1989-09-14 |
WO1987004321A2 (en) | 1987-07-30 |
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